Vacation Rentals By Owner In Chicago, IL

$496.54

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers.brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

2

Bed

1

Bath

4

Sleeps

$829.27

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

3

Bed

2

Bath

6

Sleeps

$1001.89

/ Nightly

Hotel

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, Illinois, United States

Summary:brbrDiscover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it's the perfect base for exploring Chicago. Book your stay now!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than the current photos. brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrParkingbrbrWe include parking for one vehicle in the lot directly across the street at no additional charge! Any additional vehicles will receive a discounted rate.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

4

Bed

3

Bath

8

Sleeps

$778.41

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy top floor living as this unit sits on the 9th level. The building also features a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

3

Bed

2

Bath

6

Sleeps

$1051.81

/ Nightly

Hotel

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, Illinois, United States

Summary:brbrDiscover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it's the perfect base for exploring Chicago. Book your stay now!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrParkingbrbrWe include parking for one vehicle in the lot directly across the street at no additional charge! Any additional vehicles will receive a discounted rate.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

4

Bed

3

Bath

8

Sleeps

$1085.28

/ Nightly

Hotel

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, Illinois, United States

Summary:brbrDiscover The Plymouth Chicago, a historic 1899 landmark offering 30 stylish apartments right in the heart of downtown. This apartment features a full kitchen, in-unit laundry, and comfortable living spaces, perfect for families and extended stays. Enjoy amenities like a lobby pool table, fitness center, and a rooftop with grills and stunning city views. Located steps from Printers Row, Millennium Park, and various attractions, it's the perfect base for exploring Chicago. Book your stay now!brbrbrbrThe Space:brbrThis newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king sized bed and the other three bedrooms feature double sized beds. Clean lines and modern touches create a relaxing environment to recharge. The three full sized bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrParkingbrbrWe include parking for one vehicle in the lot directly across the street at no additional charge! Any additional vehicles will receive a discounted rate.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

Bed

Bath

Sleeps

$1212.47

/ Nightly

Apartment

2-Story Penthouse -Views, Fireplace, Pool, Gym

Chicago, Illinois, United States

Summary:brbrThe Penthouses at Grand Plaza PH#4: brbrSoar above Chicago in this stunning 2-story penthouse with unmatched skyline & Lake Michigan views. This luxury 2-bed, 2-bath duplex comfortably sleeps 7. Features a private balcony, gas fireplace, and access to resort-style amenities like a pool, fitness center, and sundeck. Experience the best of the city from this unparalleled location.brbrbrbrThe Space:brbrStep into a world of light and air, where your living room feels like a private gallery suspended over the city. The two-story, floor-to-ceiling windows frame the breathtaking cityscape, while a gorgeous gas fireplace adds warmth and ambiance to your evenings.brbrbrbr-Two-story, 2-bedroom, 2-bathroom duplex apartment.brbr-Primary bedroom with a King bed, an en-suite full bath, and a spacious walk-in closet with a dresser for your belongings.brbr-Second bedroom furnished with a comfortable Queen bed.brbr-Flexible sleeping arrangements with a Queen sleeper sofa in the living room and a Full sleeper sofa in the loft.brbr-A huge, oversized private balcony to enjoy the fresh air and stunning views.brbr-Fully equipped kitchen featuring modern stainless steel appliances.brbr-A dedicated workspace for when you need to connect.brbr-Convenient in-unit washer and dryer, with detergent and fabric softener provided.brbr-Stay entertained with fast Wi-Fi and a Smart TV.brbrbrbrGuest Access:brbrGuests will have exclusive and private access to the entire two-story penthouse apartment, including the private balcony.brbrAdditionally, as our guest, you'll enjoy full access to the Grand Plaza's resort-style amenities, creating a complete luxury experience:brbr-Sparkling outdoor pool and sundeck.brbr-Outdoor kitchen and dining area, perfect for grilling and entertaining.brbr-State-of-the-art fitness center.brbr-Indoor basketball court.brbr-Outdoor running track.brbr-Business center with dedicated workstations.brbr-In-building Jewel/Osco grocery store for ultimate convenience.brbr-24-hour door staff and on-call maintenance for security and peace of mind.brbr-Discounted Indoor parking garage at $46/daybrbr-On-call maintenancebrbrbrbrThe Neighborhood:brbrRiver North is one of Chicago’s most vibrant and upscale neighborhoods, renowned for its perfect blend of culture, dining, and urban living. Just steps from the Magnificent Mile and the Chicago Riverwalk, this area offers a diverse range of attractions, from world-class restaurants and stylish cocktail bars to contemporary art galleries and iconic architecture. River North is ideal for exploring on foot, surrounded by designer boutiques, top-rated attractions, and easy access to public transit. It’s the perfect home base for both business and leisure travelers looking to experience the best of downtown Chicago.brbrbrbrGetting Around:brbr-Walk Score: 100 – steps from dining, shopping, and nightlifebrbr-50 feet to the Red Linebrbr-Near Magnificent Mile, Millennium Park, Riverwalkbrbr-Surrounded by top restaurants, coffee shops, and boutiquesbrbr-CTA Bus Stops Nearby – Multiple lines within 1 block for access to neighborhoods like West Loop, Lincoln Park, and Hyde Parkbrbr-Uber, Lyft & Taxis – Abundant and easily accessible at all hoursbrbr-Divvy Bike Station – 1 block eastbrbrbrbrOther Things to Note:brbr-Check-in is any time after 4:00 PM.brbr-Check-out is by 10:00 AM.brbr-A pack-n-play is available upon request for those traveling with young children. Please let us know in advance if you need one.brbr-A government-issued photo ID and a complete list of all guests are required prior to arrival for building registration.brbrCity of Chicago License: 2210737brbrbrbrInteraction with Guests:brbrWe are committed to ensuring you have a wonderful and seamless stay. While we respect your privacy, we are always available messaging platform to answer any questions or address any needs you may have during your visit. The building also features 24-hour door staff and on-call maintenance for any immediate building-related concerns.

2

Bed

2

Bath

7

Sleeps

$326.0

/ Nightly

Apartment

Tasteful Streeterville 1BR w/ Gym, Pool, near Navy Pier, by Blueground

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped Streeterville home with stunning high floor views over the city. (ID #CHI408)brbrDesigned with you in mindbrbrAs with any Blueground apartment, you’ll find a thoughtfully designed space complete with beautiful furniture and a fully equipped kitchen in this one bedroom property. And, thanks to our superior quality mattresses, fully stocked linens, and towels, you can relax knowing you’ll always feel comfortably at home. When you’re ready for some fun, you can take in the Chicago vibes or bring the entertainment to you with the premium wireless speaker or smart TV. brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryer in buildingbr - Elevatorbr - Swimming poolbr - Washing machine in buildingbr - Pets allowedbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is located in Streeterville, only a 5 minute walk from The Loop. One of the fastest-developing neighborhoods in Chicago, Streeterville extends out into Lake Michigan and attracts a blend of young professionals, students, and tourists. A plethora of amenities and activities exist for every lifestyle. From Navy Pier activities to luxury shopping on Michigan Avenue, it is a walkable community with easy access to entertainment.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - The apartment is in a busy location, so it will be noisy when your windows are open

1

Bed

1

Bath

2

Sleeps

$314.0

/ Nightly

Apartment

Elegant Streeterville Studio w/ Gym, Pool, near Navy Pier, by Blueground

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this pretty studio Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped Streeterville home with stunning high floor views over the lake. (ID #CHI406)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your stylish living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this Streeterville apartment has to offer. brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this studio apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryer in buildingbr - Elevatorbr - Swimming poolbr - Washing machine in buildingbr - Pets allowedbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is located in Streeterville, only a 5 minute walk from The Loop. One of the fastest-developing neighborhoods in Chicago, Streeterville extends out into Lake Michigan and attracts a blend of young professionals, students, and tourists. A plethora of amenities and activities exist for every lifestyle. From Navy Pier activities to luxury shopping on Michigan Avenue, it is a walkable community with easy access to entertainment.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - The apartment is in a busy location, so it will be noisy when your windows are open

1

Bed

1

Bath

2

Sleeps

$504.91

/ Nightly

Condo

NEW! Heart of East Village 2-Bed 2-Bath Peaceful Oasis

Chicago, Illinois, United States

Enjoy a peaceful escape at this stylish and modern home. You'll love thebrbrquaint tree-lined street that is just steps away from amazing restaurants, anbrbrexciting nightlife and all that the city has to offer. Inside you'll find yourbrbrsanctuary, including an ensuite primary bathroom with a relaxing jacuzzi tub,brbrthe convenience of an in-unit washer and dryer. Or, perhaps you'd like to havebrbra glass of wine on the back patio that has a view of the John Hancockbrbrbuilding. This home has all you need! brbrGeneral Policies: brbr brbrGuest Age Policy – Guests aged 18-24 may book on an exception basis. Pleasebrbrinclude your age, reason for booking, and who will be staying with you in yourbrbrinquiry. brbr brbrLocal Guest Policy – Local guests are permitted to book on an exception basisbrbronly. Parties, gatherings, and group events are strictly prohibited.brbrUnauthorized gatherings or events will result in termination of reservationbrbrwithout refund. brbr brbrPrimary Guest Responsibility – The booking guest must stay for the fullbrbrduration and is responsible for all guests. If booking on behalf of someonebrbrelse, please contact us to discuss exceptions. brbr brbrParking – Street parking may be available but is not guaranteed. Read allbrbrposted signs to avoid tickets or towing. To secure a spot, use parking appsbrbrlike SpotHero or ParkWhiz. brbr brbrCity Noise – Some ambient noise is part of city living. brbrbrbr

2

Bed

2

Bath

4

Sleeps

$774.07

/ Nightly

Private Vacation Home

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago, Illinois, United States

Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home brought to you by CN Realty (Discounts available for stays beyond 4 days - email for pricing!)brbrThis home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here!brbrThis is a top of the line Custom Single Family home. You will not find a nicer, larger, newer, Single Family Home in Chicago. The house is 4200 square feet, it has 2 decks, an attached 2 car garage (you don't want to walk outside in the winter to get to your car). The master suite is top of the line with 2 huge closets, a marble bath with Jacuzzi tub and steam shower.brbrThis home is also an easy drive to the McCormick Place for Conventions and an easy drive or bus straight down Ashland to the United Center to catch a Blackhawks or Bulls game or other event.brbrJust check out the pictures and email for more details!brbrYes we are Licensed! # 2262746 so we will be around for your stay! We will not be shut down by the city by exceeding their limited # of stays for non licensed properties!brbr

Bed

Bath

Sleeps

$508.79

/ Nightly

Apartment

52nd Floor MagMile Penthouse Views Fireplace Pool

Chicago, Illinois, United States

Summary:brThe Penthouses at Grand Plaza PH#9brExperience elevated city living from this stunning penthouse, soaring 52 stories above Downtown Chicago. Enjoy floor-to-ceiling windows, a designer fireplace, and breathtaking views of Lake Michigan. Perfectly positioned between the elegance of the Magnificent Mile and the vibrant charm of River North, this residence offers refined comfort and an unforgettable stay in one of Chicago’s premier locations.brThe Penthouses at Grand Plaza. License #2210737brbrThe Space:br-OVERSIZED 1 bedroom apartment with floor-to-ceiling windowsbr-Large Living room with gas fireplacebr-Formal Dining areabr-Comfortable queen bed + plush seating area and large deskbr-Fully equipped kitchen with stainless steel appliancesbr-Fast Wi-Fi and Smart TVbr-Washer & dryer with detergent and fabric softener providedbrbrGuest Access:brEnjoy resort-style access to Grand Plaza's luxury amenities:br-Jewel/Osco is located in the buildingbr-Outdoor pool with sundeckbr-Outdoor kitchen & dining area for grilling and entertainingbr-Fitness center with state-of-the-art equipmentbr-Indoor basketball court and outdoor running trackbr-Business center with workstationsbr-24-hour door staff for secure entry and assistancebr-Discounted Indoor parking garage at $41/daybr-On-call maintenancebrbrThe Neighborhood:brRiver North In a city known for its style and art, no other neighborhood better represents Chicago.brbrWith more clubs, galleries and studios than any other part of Chicago, River North attracts creatives looking for a trendy community full of inspiration. A little over three square miles in size, River North is home to an estimated 27,000 people.brbrFoodies love River North. With new restaurants popping up in the neighborhood all the time, eating out never gets boring. When you’re looking to get outside, there are no shortage of options. Locals often enjoy picnics at Ward (A. Montgomery) Park on the north bank of the river, meet-ups at one of the neighborhood’s dog parks and strolls along the winding riverside.brbrOn top of great food and beautiful riverfront, locals benefit from the area’s location and well-connected transport system, high quality grade schools and several sports facilities for solo and team activitiesbrbrGetting Around:br-Walk Score: 100 – steps from dining, shopping, and nightlifebr-50 feet to the Red Linebr-Near Magnificent Mile, Millennium Park, Riverwalkbr-Surrounded by top restaurants, coffee shops, and boutiquesbr-CTA Bus Stops Nearby – Multiple lines within 1 block for access to neighborhoods like West Loop, Lincoln Park, and Hyde Parkbr-Uber, Lyft & Taxis – Abundant and easily accessible at all hoursbr-Divvy Bike Station – 1 block eastbrbrOther Things to Note:br-Check‑in: after 4:00 PMbr-Check‑out: by 10:00 AMbr-Children: Welcome - pack-n-play available upon requestbr-No events or parties allowedbr-No pets permittedbr-No smoking anywhere in the unitbr-Government-issued photo ID required before arrivalbr-Guest list required prior to check-in

1

Bed

1

Bath

4

Sleeps

$852.71

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbr*Please note that this unit is currently undergoing a full repaint. As a result, wall colors and decor may vary slightly from what is shown in the photos. However, the layout and bed sizes will remain exactly the same.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

Bed

Bath

Sleeps

$844.82

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best!brbrbrbrThe Space:brbrThis newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom features a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

3

Bed

2

Bath

6

Sleeps

$557.42

/ Nightly

Hotel

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers.brbrbrbrThe Space:brbrThis newly renovated plcae is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

2

Bed

1

Bath

4

Sleeps

$580.95

/ Nightly

Hotel

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym. Just minutes from all attractions, it’s an ideal home base for business travelers and city explorers.brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

2

Bed

1

Bath

4

Sleeps

$584.6

/ Nightly

Apartment

Plymouth Collection: Top Floor with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago, a historic 1899 landmark in the heart of Printers Row. Beautifully renovated in 2018 and thoughtfully redesigned in 2026, this stylish studio blends classic Chicago architecture with modern comfort. Enjoy top-floor living on the 11th floor, with added privacy and abundant natural light. The space includes a full kitchen, cozy living area, and in-unit laundry—perfect for longer stays. Play pool in the lobby, head up to the rooftop to grill, or workout in the gym!brbrbrbrThe Space:brbrThis newly renovated place located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away!brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping area features two comfortable beds both with double sized beds designed for restful nights, whether you’re visiting for business or a weekend getaway. Clean lines and modern touches create a relaxing environment to recharge. The bathroom is bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable.brbrbrbrAmentiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay. brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in.brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: One bedroom features a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

Bed

Bath

Sleeps

$858.56

/ Nightly

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Summary:brbrWelcome to The Plymouth Chicago—an 1899 landmark brought to life with modern style and comfort! This freshly redesigned studio features a full kitchen, cozy living area, and in-unit laundry, making it perfect for longer stays. Enjoy the building’s lobby featuring a pool table, fitness center, and stunning rooftop with grills. Steps from Printers Row cafés, Millennium Park, and all of downtown, it’s the ideal spot for both work and play. Book your stay and experience Chicago at its best!brbrbrbrThe Space:brbrThis newly renovated place is located in the historic Printers Row at the iconic Plymouth Building. Originally built in 1899 during Chicago’s booming printing and publishing era, this building has been beautifully preserved and thoughtfully renovated in 2016 when it was marked as an official historic landmark. The entire building was redesigned in March 2026, complete with new furniture and amenities. Nestled just south of The Loop, you’ll be surrounded by historic architecture, charming cafés, bookstores, and some of Chicago’s most iconic attractions—all just minutes away.brbrbrbrLiving Room & KitchenbrbrDesigned for both comfort and convenience. The inviting living space offers a cozy place to relax after a day exploring the city or attending meetings downtown. Large windows provide natural light while the thoughtfully designed layout makes the space feel open and welcoming. The fully equipped kitchen includes everything you need to cook a meal, make your morning coffee, or enjoy a quick bite before heading out to explore Chicago.brbrbrbrBedroom & BathroombrbrThe sleeping areas features a comfortable beds designed for restful nights, whether you’re visiting for business or a weekend getaway. One bedroom feature a king bed while the other two feature double beds sleeping a total of 6 guests. Clean lines and modern touches create a relaxing environment to recharge. Both bathrooms are bright and modern, stocked with essentials and fresh towels to make your stay easy and comfortable. All bedrooms have been recently painted and might be slightly different than current photos. brbrbrbrAmenitiesbrbrGuests also have access to wonderful shared spaces throughout the building. The stylish lobby includes a lounge area with a pool table and a conference room, perfect for casual meetings or relaxing with friends. Head up to the rooftop to enjoy outdoor seating, grills, and a ping pong table—an ideal spot to unwind, enjoy the skyline views, and experience Chicago from above. The fitness center is open 24/7 and is equipped with all the essentials needed for a complete workout.brbrbrbrGuest Access:brbrGuests will have access to the entire unit as well as all common areas.brbrbrbrThe Neighborhood:brbrLocated just south of downtown, Printers Row is one of Chicago’s most charming and historic neighborhoods. Once the center of the city’s printing and publishing industry in the late 1800s, the area is now known for its beautiful brick loft buildings, quiet tree-lined streets, and classic Chicago character. Today, visitors can enjoy cozy cafés, local restaurants, bookstores, and easy access to nearby attractions like Grant Park, Millennium Park, and The Loop. With its mix of history, walkability, and downtown convenience, Printers Row offers a perfect blend of neighborhood charm and city energy.brbrbrbrGetting Around:brbrFor guests driving to the building, there is a paid parking lot directly across the street and several other parking garages within walking distance. We recommend using SpotHero to find the best prices during your stay.brbrbrbrIf arriving by train, several stations on the Chicago 'L' are within walking distance. The closest is Harrison Station, about a 4-minute walk away, providing direct access north to downtown attractions and south to neighborhoods across the city. LaSalle Station is also nearby and offers a direct train to O'Hare International Airport.brbrbrbrFor travelers arriving by air, the property is approximately a 20-minute drive from Chicago Midway International Airport and about 30–40 minutes from O'Hare International Airport depending on traffic. Taxis, rideshares, and CTA buses are widely available throughout the area, and many of Chicago’s top destinations are easily reachable by foot from the building.brbrbrbrOther Things to Note:brbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the unit or on the rooftop.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrRooftop: The rooftop will be open from 8AM - 10PM. Please clean up after yourself if you utilize this space.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $250 will be required before check in. brbrbrbrHeating and Cooling: As part of The Plymouth’s historic charm, the building operates on a centralized, seasonally adjusted climate system. This means the property runs on either heating or cooling depending on the season. Guests can personalize their in-room unit for comfort, including adjusting temperature and turning it off, as well as opening and closing windows, but cannot switch between heat and AC. We appreciate your understanding as we provide a balanced and comfortable experience for all guests.brbrbrbrPlease note: Two bedrooms feature a partial-height wall that does not extend fully to the ceiling, making the space partially open at the top that can be viewed on the living room photos. brbrbrbrLicense Number: 3069885brbrbrbrInteraction with Guests:brbrSeamless Check-In: We'll provide you with a unique keyless entry code before your arrival, allowing you to check in at your convenience. No need to worry about coordinating key handoffs or arrival times.brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.

3

Bed

2

Bath

6

Sleeps

$552.92

/ Nightly

Condo

NEW! Newly Renovated 3BR/2BA in Heart of Andersonville

Chicago, Illinois, United States

Amazing location! Experience the unparalleled comfort and style of this brand-brbrnew, fully renovated 3BR/2BA condo nestled in the heart of Andersonville!brbrSteps to Clark St shops, dining. 7min to beach. Stylish, full eat-in kitchen,brbrdining area, workspace, Wi-Fi, 65 4K TV, central AC/heat, in unit W/D, winebrbrcooler. brbr brbrSpa-inspired bathrooms: en suite w/heated towel rack, rainfall shower, doublebrbrvanity, Italian tile. brbr brbrFree easy street parking, close to transit, and nearby parks. Enjoy urbanbrbrluxury! brbrSpa-inspired bathrooms: en suite w/heated towel rack, rainfall shower, doublebrbrvanity, Italian tile. brbr brbrFree easy street parking, close to transit, and nearby parks. Enjoy urbanbrbrluxury! brbrGeneral Policies: brbr brbrGuest Age Policy – Guests aged 18-24 may book on an exception basis. Pleasebrbrinclude your age, reason for booking, and who will be staying with you in yourbrbrinquiry. brbr brbrLocal Guest Policy – Local guests are permitted to book on an exception basisbrbronly. Parties, gatherings, and group events are strictly prohibited.brbrUnauthorized gatherings or events will result in termination of reservationbrbrwithout refund. brbr brbrPrimary Guest Responsibility – The booking guest must stay for the fullbrbrduration and is responsible for all guests. If booking on behalf of someonebrbrelse, please contact us to discuss exceptions. brbr brbrParking – Street parking may be available but is not guaranteed. Read allbrbrposted signs to avoid tickets or towing. To secure a spot, use parking appsbrbrlike SpotHero or ParkWhiz. brbr brbrCity Noise – Some ambient noise is part of city living. brbrIf you are bringing a pet, only 1 dog is permitted. Pets are limited to 1brbrunless it's a service pet and cats are not allowed. Please send an inquiry ifbrbryou have further questions.brbrbrbr

Bed

Bath

Sleeps

$326.61

/ Nightly

Apartment

South Loop 2 Bedroom Apt

Chicago, Illinois, United States

Summary:brbrSouth Loop 2 bedroom apartment with 2 bathrooms. We are centrally located and very easy to get anywhere in the city! Walking, public transportation or Uber is a great way to get around! Two stories.brbrbrbrThe Space:brbrWe have 2 bedrooms with 2 bunk beds with full size mattresses and a queen size air mattress and a couch for sleeping arrangements. If doubled up, can sleep a MAXIMUM of 13 people. We are 1 block from the El Chicago's main transportation, the building is insulated so even with the train so close, you can hear it but he building does a great job of muffling the noise.brbrbrbrTwo story unit, there are entrances on each floor or there is a staircase inside the unit but it is very SKINNY. If you struggle with stairs we suggest using the building staircase.brbrbrbrGuest Access:brbrThe entire unitbrbrbrbrThe Neighborhood:brbrSet next to Museum Campus and including historic Printers Row, the large South Loop is a lively hub of classic bars and diverse restaurants, plus longtime clubs Jazz Showcase and Buddy Guy's Legends. Students and creative types frequent the Museum of Contemporary Photography, while blues label Chess Records offers tours of its recording studio.brbrbrbrGetting Around:brbrWe are right next to the train, so public transportation is very easy to get to and can take you anywhere in Chicago. Ubers are plentiful as well.brbrbrbrOther Things to Note:brbrBefore we can confirm any booking, we do need to know:brbr1. What brings you into town brbr2. How many people will be staying at the home brbr3. Do you expect any visitors, if so how many brbrbrbrWe may require an ID & signed Rental Agreement or a refundable deposit prior to check in.brbrbrbrWe do have Ring Cameras outside the property. Any blocking of the cameras will lead to an automatic eviction, forfeiture of security deposit, no refund and a fine. Please do not block these cameras.brbrbrbrWe do not have keys or access to our mailbox.brbrbrbrHOUSE RULESbrbr11:00 pm Quiet HourbrbrWe do NOT allow late check out. There is a charge of $25/10 min after 11AM. brbrMust 21+ to BookbrbrNo smoking or Vaping (of anything) inside the unit. $500 fine if home smells like smoke.brbrMust book for total number of guests staying/visiting the home. $250 per unauthorized guest/night. Ring cameras on the exterior of the property. These do record when it captures motion. Blocking of cameras will lead to eviction and $1000 fine. NO EXCEPTIONS!brbrIf a security team is called due to an infraction of the house rules, the guest agrees to pay for the security team ($500 minimum) and the duration of the reservation, even if removed by the security team due to the infraction.brbrDo not cover Ring Cameras, this will lead to an eviction and forfeiture of security deposit.brbrPlease DO NOT flush feminine products/paper towels/any foreign substance down the toilet (ONLY toilet paper). It is not good for the pipes and if there is an issue we may pass the charge onto the guest.brbr$500 for any unauthorized pets per nightbrbrRental agreement, ID, and/or security deposit may be asked prior to bookingbrbrbrbr$250 lockout fee if needed to call a locksmith to let in. If keys at property and lost this charge will apply. If no keys, this will not be applicable unless tampering was made with our digital door lock systembrbrbrbrPlease no burning of candles, incense, or anything else in the home. If done, this will be treated as “smoking” in our house rules. Thank you.brbrbrbrWe only provide the initial supplies for the stay. If more are needed throughout the trip, It will be the guest's responsibility.brbrbrbrLicense number: R24000120270brbrbrbrInteraction with Guests:brbrOur concierge team is available from 10am–8pm Sunday-Thursday and 10am–12am Friday and Saturday. Messages received outside of these hours will be addressed promptly the following day. We curate a refined, hands-off experience so you can immerse yourself in comfort and relaxation — with attentive support whenever needed.brbrbrbrSunday - Thursday: 10am - 8pmbrbrFriday & Saturday: 10am -12am

2

Bed

2

Bath

13

Sleeps

Vacation Rentals By Owner In Chicago, IL

$496.54

$829.27

$1001.89

$778.41

$1051.81

$1085.28

$1212.47

$326.0

$314.0

$504.91

$774.07

$508.79

$852.71

$844.82

$557.42

$580.95

$584.6

$858.56

$552.92

$326.61

Rent a place that suits your needs

Most popular vacation rentals in Chicago

$2319.21

$2427.16

$2731.80

$2999.50

$3259.71

$3780.16

$320.07

$317.86

$318.18

$318.68

Most Popular Cities in Illinois