Vacation Rentals By Owner In Chicago, IL

Lakeview is a great location with a mixed residential and business feel. This newly redecorated studio is larger than most in the neighborhood with a sleeping area and living area in the main space. There is a large kitchen, with new stainless steel appliances . The apartment is walking distance from Wrigley Field , Boystown, grocery stores, CTA public transportation, restaurants , sport bars and more.

Cozy Studio In Lakeview, Near Wrigley field

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1264.75

Enjoy a stylish and spacious Chicago stay in this beautifully designed 3-bedroom, 2-bath home located on the city’s West Side. Perfect for families, groups, and business travelers, this property offers a clean modern design, private balcony, and an open layout that makes relaxing and gathering effortless.brWith comfortable furnishings, a full kitchen, and thoughtfully designed interiors, this home provides everything needed for a smooth and enjoyable Chicago stay.brbr♥ Why Guests Love Staying Herebr• 3 private bedrooms with queen beds for restful sleepbr• 2 full bathrooms for convenience and group comfortbr• Private balcony with outdoor seatingbr• Open-concept living, dining, and kitchen layoutbr• Full kitchen with essential appliances for easy mealsbr• Bright, modern interiors with hardwood floorsbr• Designed for both relaxation and functionalitybrbr❋ The SpacebrStep into a bright and welcoming home where modern design meets everyday comfort. The open-concept layout connects the living room, dining area, and kitchen, creating a natural flow for socializing, dining, or unwinding after a long day.brThe space is thoughtfully arranged to give guests both shared areas for gathering and private bedrooms for rest. Clean finishes, stylish décor, and natural light create a warm and polished atmosphere throughout.brbr➤ Sleeping ArrangementsbrBedroom 1br• 1 Queen bedbr• Direct access to balconybrBedroom 2br• 1 Queen bedbrBedroom 3br• 1 Queen bedbrBathroomsbr• 2 full bathroomsbr• One with walk-in showerbr• One with tub and shower combinationbrbr➤ Kitchen & DiningbrThe kitchen is fully equipped for everyday cooking and group meals, offering both convenience and functionality.brKitchen Featuresbr• Refrigeratorbr• Gas stove and ovenbr• Microwavebr• Dishwasherbr• Coffee makerbr• Toasterbr• Electric kettlebr• Sink and ample counter spacebr• Cabinet storagebrDining Areabr• Glass dining tablebr• Seating for 6 guestsbrbr➤ Living & ComfortbrThe living area is designed for relaxation and comfort, providing a welcoming space to unwind.br• Spacious seating areabr• Natural light from multiple windowsbr• Modern lighting throughoutbr• Ceiling fans for added comfortbr• Clean, contemporary furnishingsbrbr➤ Outdoor SpacebrStep outside to your private balcony, a perfect extension of the living space.br• Outdoor seatingbr• Table for drinks or coffeebr• Covered area for comfort in any weatherbrbr➤ Location & Nearby AttractionsbrConveniently located with easy access to major Chicago destinations.br• United Center – home of the Chicago Bulls and Blackhawksbr• Rush University Medical Center and Illinois Medical Districtbr• University of Illinois Chicago (UIC)br• Garfield Park Conservatorybr• Quick access to downtown Chicago, dining, and entertainmentbrbr➤ Perfect Forbr• Families visiting Chicagobr• Groups traveling togetherbr• Business travelersbr• Medical stays near nearby hospitalsbr• University visitsbr• Weekend city getawaysbrbr★ Guest ExperiencebrGuests appreciate homes like this for the balance of space, comfort, and functionality. With three separate bedrooms, two full bathrooms, and a shared living area, the layout is ideal for both privacy and connection.brbr✓ Book Your StaybrExperience a comfortable and convenient Chicago stay in a space designed to meet the needs of modern travelers. Whether visiting for work or leisure, this home offers the right combination of location, comfort, and thoughtful design.brReserve your stay today and enjoy a seamless Chicago experience.

Modern 3BR Downtown Chicago Retreat Near United Center & West Loop

Chicago, Illinois, United States

Bed

Bath

8

Sleeps

$253.97

Looking for a luxurious getaway in the heart of the city Look no further than this stunning 3 bedroom, 2 bath modern apartment. Perfectly situated just minutes from the bustling city center, this apartment combines the comfort and convenience of a modern home with all the amenities you need to make your stay unforgettable.brbrFeaturing a chic and stylish aesthetic, this apartment boasts plenty of natural light, sleek furnishings, and contemporary art pieces throughout. In the spacious living area, you'll find a plush couch and state-of-the-art entertainment center, perfect for relaxing after a long day of sightseeing. The adjoining kitchen is fully equipped with high-end stainless steel appliances, granite countertops, and all the utensils and cookware you need to whip up a delicious meal.brbrEach of the three bedrooms features a comfortable queen-size bed, soft linens, and plenty of storage space for all your belongings. The two pristine bathrooms are stocked with fluffy towels, organic toiletries, and all the modern amenities you need to refresh and rejuvenate during your stay.brbrOther features of this stunning apartment include high-speed Wi-Fi, flat-screen TVs in every room, a private balcony with stunning city views, and a full-size washer and dryer for added convenience. Whether you're here for a romantic weekend, a family vacation, or a business trip, this modern luxury apartment is the perfect home base for all your adventures in the city.

Modern luxury apartment in West Town Chicago

Chicago, Illinois, United States

Bed

Located in the heart of Lakeview, between Lincoln and Southport, you will be wowed by the 17-foot ceilings and city views from the main floor terrace, 2nd floor office and 3rd floor private roof deck. This 3-bedroom, 2-bath condo in a boutique elevator building is an entertainer's heaven but also offers all the comforts of home in its 2,600 SF. The location is extremely walkable to multiple coffee shops, restaurants/bars (our favorites are one block way - Que Rico, Sal's, Southport Betty's, Sidestreet Saloon, Heritage, Dopio, etc.) grocery stores, post office, dry cleaner - you name it. This well-appointed home will satisfy every Chicago-lover's dreams. All 3 bedrooms are spacious with plenty of closet space. Main areas include an additional office, living room with TV, massive kitchen island, dining table and living room with gas fireplace. The primary suite was remodeled in 2024 and offers heated floors, standalone tub and gorgeous marble tile -- a retreat ready for relaxation. One heated garage space and utilities included. The condo is available for stays 60+ days or more from October - June. Please reach out with any questions!

Bath

8

Sleeps

Select Dates for Price

Condo

Soaring ceilings, city views and private rooftop deck!

Chicago, Illinois, United States

Bed

Bath

6

Sleeps

$208.0

Discover the best of Chicago, with this one bedroom apartment in The Loop with high floor views over the city. It’ll be easy to simply show up and start living in this furnished apartment with its fully equipped kitchen, living room, and our dedicated, on-the-ground support. (ID #CHI668)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 lovely 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 The Loop apartment has to offer. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Doormanbr - Dryerbr - Elevatorbr - Washing machinebr - Loungebr - Pets allowedbr - Rooftop BBQbrbrArrival 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 situated in the most dynamic and convenient place to live in Chicago, The Loop. With its endless shopping, fine dining, stunning park, river and lake views, and entertainment opportunities, everything is possible at a moment’s notice. The area is a cultural getaway for professionals and students, who can combine work with pleasure. Discover landmark buildings like the Willis Tower and The Art Institute of Chicago. Millenium Park, near Lake Michigan, is always worth a visit. The Loop is within reach of accessible transportation, offering non-stop public transit, buses, and taxis. Union Station is approximately a 10 minute train ride.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 - Building requires 48h to confirm the booking and validate the required documents

Trendy Loop 1BR w/ Gym, Roof & Lounge, same block as L, by Blueground

Chicago, Illinois, United States

Bed

Bath

Sleeps

$390.0

* Clean, peaceful 3BR/2BA unit in a quiet 3-flat * Approx. 30 stairs to reach this 3rd-floor walk-up * Known for comfort, calm, and exceptional cleanliness * Skyline views + 3 private decks for relaxing or reading * Cozy, low-tech stay w/ Smart TV in living room & fast WiFi * Full kitchen, free street parking, family-friendly * Add-ons: seasonal bouquets, private chef dinners by request Experience a Chicago stay like no other at the Farmstay at Herban. Located on a working urban farm, this peaceful 3-bedroom, 2-bath unit offers a unique blend of relaxation, comfort, and natural beauty—just minutes from downtown and some of the city’s best dining and cultural spots. Tucked in a quiet, centrally located neighborhood, you’ll be close to downtown, Restaurant Row, and hidden neighborhood gems. Inside, enjoy: *12-ft ceilings and abundant natural light A fully equipped chef’s kitchen with modern finishes *Spa-style bathrooms for a relaxing retreat *1,600 sq ft of professionally decorated living space *3 private patios and a seasonal rooftop deck with skyline and farm views This low-tech, high-comfort space is perfect for families, couples, creatives, and anyone seeking rest and reconnection. Guests love the peaceful energy, spacious layout, and exceptional cleanliness. Available for vacation stays or as a filming location, the Farmstay at Herban offers a stay that’s as memorable as it is restorative. You'll have full access to the spacious 1,600 sq ft unit, including: Three private patios—perfect for relaxing, reading, or enjoying your morning coffee A bright, peaceful living space with modern comforts The unit is located on the third floor of a walk-up building (approx. 30 stairs). There is no elevator, so please plan accordingly. Want to enjoy more outdoor space Our courtyard is available upon request—just let us know! We respect your privacy but are always nearby if you need anything! Whether it’s a quick question, fresh flowers, or a curated recommendation, we’re happy to help make your stay feel personal and relaxed. We are very close to public transit. The CTA blue and green L stations and and block away from the Jackson bus. If you are unfamiliar with Chicago, we recommend getting around by car. We provide a detailed orientation guide to the house and a list of recommendations of things to see & do during your stay.

Private Vacation Home

Urban Farm Stay w/ Skyline Views + Free Parking

Chicago, Illinois, United States

Bed

Bath

7

Sleeps

$79.51

Discover the beauty of Chicago from this private bedroom apartment. This delightful space features a cozy living room with a sofa bed thats available for booking separately, dresser, work desk, mini portable closet and cupboard. Its perfect for relaxing after a day of exploring the city as its less than 30 minutes to the loop. The bedroom boasts a comfortable queen bed for a restful night's sleep. Enjoy the convenience of amenities like WiFi, AC, and a paid community washing machine. Unwind after a long day of traveling. Make your holiday one for the books with a stay at our place. There is two bottles of water per guest in the fridge. A water filter to refill your water with when needed as long as the water filter is filled up after. There is shelf space at the top of the fridge for your food. Items in the kitchen outside of pots, utensils and plates can be used if asked first.

Chic private bedroom housing close to public transportation to the loop.

Chicago, Illinois, United States

Bed

Bath

Sleeps

$191.26

Newly renovated condo, perfect for up to 4 guests. This spotless space is meticulously cleaned and maintained to ensure a comfortable stay. Enjoy the fully equipped kitchen with stainless steel appliances and all the cookware you need to prepare a great meal. The condo also features an advanced washer and dryer combo for your convenience. A striking hand-painted mural of Michael Jordan adds a unique touch to the décor. Located just minutes from I-290 and a short 7-minute drive to downtown Chicago, you're close to vibrant nightlife, restaurants, and entertainment. This cozy and impeccably clean space has everything you need for a comfortable, home-away-from-home experience.

Condo

Relaxing Chicago Vibe - Minutes away from major attractions

Chicago, Illinois, United States

Bed

Bath

Sleeps

$693.45

Our home is located in the quiet, but centrally located Buena Park neighborhood in an updated antique building. The location provides easy access to the Red and Purple train lines, as well as multiple bus lines to move you throughout the city. Nearby you will find many bars, restaurants, concert venues, and other great Chicago sites such as the Green Mill. Walking distance to Wrigley Field and Clark St. bars, Montrose Beach, Lakeview and Boystown bars.brThe spacebrRoommate style 2 bedroom condo. Each room has an attached bathroom. The back room has access to the back entrance of the building. The condo comes with washer and dryer. All kitchen appliances are new. There is plenty of room to spread out and make yourself comfortable. Wifi is provided, as well as toiletries, linens & towels, hair dryer, ambient noise machine, umbrellas, iPhone charger with Bluetooth speaker, and other creature comforts. I will also provide you with the basics (folding chairs, beach towel, picnic and beach blanket, large hand cooler, speaker, etc.,) for an enjoyable time at the beach, lake, riverwalk, or park.brbrRoom #1- The space is a large private room w/private entrance, bathroom, and fully furnished patio -all for your use only. This room is separated by two doors and a hallway from the rest of the condo, so you have full privacy, especially if you decide to use your private entrance. There is a queen bed that sleeps 2 and a twin folding bed (see last picture) that sleeps 1. The room also comes with a SAMSUNG 30 - 100 The Freestyle FHD HDR Smart Projector Home Theater. The bathroom has been recently renovated. This room has a kitchenette with a medium side fridge, microwave, Keuring coffee maker, air fryer, dishes, silverware, glassware, and a dinning room table for four.brbrRoom #2- This room has its private bathroom. There is a queen bed that sleeps 2 and a twin folding bed (see last picture) that sleeps 1. Two large closets. brbrThe train runs behind the building so expect occasional, but brief noise. No Parties are allowed- only the guests registered can be in the property unless you obtain special permission from me. Outdoor cameras monitor the back and front entrance.brGuest accessbrThe whole condobrRegistration numberbrR22000088593

Condo

SuperHost Large Roommate style 2 Bedroom, 2 Bath, Patio, Sunroom, L Kitchen

Chicago, Illinois, United States

Bed

Bath

7

Sleeps

$154.0

Feel at home wherever you choose to live with Blueground. You’ll love this beautiful West Loop furnished one bedroom apartment with its modern decor, fully equipped kitchen, and comfortable living room. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI1304)brbrDesigned with you in mindbrbrGorgeous furniture, fully equipped kitchen, smart TV, and a premium wireless speaker are just a few of the amenities you’ll find inside this one bedroom apartment. Ideally located in Chicago, you’ll find a lot to love outside as well. When you’re ready to relax, you’ll be happy to discover every Blueground bedroom comes with superior quality mattresses, fully stocked linens, and cozy towels. We handle everything so you can simply show up and start living. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Doormanbr - Dryerbr - Elevatorbr - Game roombr - Swimming poolbr - Washing machinebr - Loungebr - Pets allowedbr - Rooftop BBQbrbrArrival 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 LocatedbrbrLocated in West Loop, this furnished rental invites you to explore the edges of downtown Chicago. From endless dining and bar options to art galleries and stylish shops, West Loop has emerged with so much to offer daily. During weekends, residents savor trips to the Chicago French Market and the vibrant strip of Randolph Street. The latter is known as “Restaurant Row” and is lined with some of the city’s best eateries. Fulton Market, one of the hippest and fastest-growing neighborhoods, is ideal for dinner and drinks. Union Station is only a 5 to 10 minute walk away.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.

Blueground | West Loop, rooftop, nr Union Park

Chicago, Illinois, United States

Bed

Bath

Sleeps

$249.34

Welcome to your contemporary getaway in the vibrant South Side of Chicago! This stylish 3-bedroom Airbnb is perfect for families, friends, or business travelers seeking comfort and convenience. Situated directly across from Chicago State University, this property boasts easy access to I-94 one of Chicago's major expressways. Explore downtown Chicago and two casinos within 10 miles. Public transportation within walking distance. Book your stay today and enjoy all that Chicago has to offer!

Chic Retreat, Chic Retreat Your Urban Getaway

Chicago, Illinois, United States

Bed

Bath

Sleeps

$364.33

Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/1 bath with a sunny private patio deck in the rear with everything you need for a relaxing getaway in Chicago. It is walking distance to everything you need: grocery store (5 min walk), pharmacy (3 min walk), bars + restos (5 min walk), Brown line station Paulina (9 min walk), Hamlin Park (6 min walk), Wrigley Field (8 min drive). On-street parking is permitted.brThe spacebrThe apartment is the entire first floor of a wonderful 3-storey home. It has front-facing living room with large bay window, spacious kitchen, a tropical-themed full bathroom, 2 bedrooms with queen size beds (including one with a private entrance onto the rear patio deck and a working space), and a full sized office/den. Amenities include a large, brand new 65 smart TV in the living room, 50 smart TV in the main bedroom, WiFi, streaming services (Netflix, HBO Max, Disney), fully equipped kitchen, dining table with room for 6, en-suite washer + dryer, 2 work areas with desks and monitors, BBQ, smart locks for access. Backyard is shared with owner. Dogs under 30 lbs are allowed.brGuest accessbrGuests are welcome to use their own private rear patio deck with great sun exposure, patio furniture, and a BBQ for their own use.brRegistration numberbrR22000087251

2BD/1 BA with summer patio in quiet Roscoe Village

Chicago, Illinois, United States

Bed

Bath

4

Sleeps

$167.0

Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped East Hyde Park home with stunning high floor views over the city. (ID #CHI1157)brbrDesigned with you in mindbrbrGorgeous furniture, fully equipped kitchen, smart TV, and a premium wireless speaker are just a few of the amenities you’ll find inside this one bedroom apartment. Ideally located in Chicago, you’ll find a lot to love outside as well. When you’re ready to relax, you’ll be happy to discover every Blueground bedroom comes with superior quality mattresses, fully stocked linens, and cozy towels. We handle everything so you can simply show up and start living. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - 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.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 is located near a railway, so expect to hear moderate noise when trains passbr - The building's sundeck is closed during winter months

Blueground | Hyde Park, AC, w/d, nr museum

Chicago, Illinois, United States

Bed

Bath

Sleeps

$79.0

Feel at home wherever you choose to live with Blueground. You’ll love this pretty East Hyde Park furnished one bedroom apartment with its modern decor, fully equipped kitchen, and spacious living room with great views. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI1159)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. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - 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.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 is located near a railway, so expect to hear moderate noise when trains passbr - The building's sundeck is closed during winter months

Blueground | Hyde Park, AC, w/d, nr museum

Chicago, Illinois, United States

Bed

Bath

Sleeps

$293.02

2nd-floor unit with two flights of stairs. Older building with radiant heat managed by the building.brbrThis apartment is conveniently located about 30 minutes from O’Hare International Airport. Close to hospitals, schools, stores, and highways—ideal for business or leisure stays. Enjoy nearby restaurants, bars, groceries, and parks all within walking distance. A quieter alternative to downtown, yet just 10 minutes from Wicker Park, Lincoln Park, and Logan Square.brbrOther things to notebrWe do not have designated parking but free street parking is available in the neighborhood. That said, please take care to read any signs indicating no parking or tow zones to avoid any issues. Parking availability can fluctuate depending on the time of day, and if you arrive later in the evening, there’s a chance that spots might be harder to find.brbrIn case you run into this situation, we suggest using the SpotHero app or ParkWhiz to easily locate an affordable and convenience parking spot nearby.brbrbr**HOUSE RULES**brbrbrWe want you to have a comfortable and enjoyable stay! To help keep the space safe, clean, and pleasant for everyone, please review and follow the house rules below. Failure to comply may result in cancellation or additional charges.brbrShoes off, please. Kindly remove shoes upon entering the unit.brbrNo smoking anywhere inside the unit or on the property. Smoking will result in immediate cancellation and a $200 damage fee.brbrNo drugs, including marijuana.brbrNo illegal activities anywhere on the property.brbrNo parties or events.brbrNo outside visitors.brbrNo overnight guests without prior approval from the host.brbrFood storage: Please store all food in designated areas and do not leave food out to help prevent pests.brbrKitchen use: Feel free to use the kitchen, but please clean up after yourself. Wash dishes, wipe counters, stove, and microwave. No dirty dishes left in the sink overnight.brbrDamages: If anything is broken or damaged, please let us know right away so we can arrange repair or replacement.brbrCheckout cleaning:brPlease wash dishes, return moved furniture to its original place, and take out the trash before checkout.brThe standard cleaning fee covers normal turnover cleaning. If the unit is left excessively dirty (dirty dishes, trash left throughout the unit, etc.), an additional cleaning fee of up to $100 may apply.brbrTowels & linens: Provided for your entire stay. If you need extras, please let us know in advance. A $50 fee applies to cover the cleaner’s trip. Paid laundry facilities are available in the building.brbrLost keys: A $300 fee applies for lock and key replacement. Please note that lost keys cannot be replaced immediately, and you may temporarily lose access to the unit and building amenities.brbrQuiet hours: Please observe quiet hours from 10:00 PM – 8:00 AM.brbrLate checkout: Checkout time is 11:00 AM. Late checkout without prior approval will incur a $50 fee, which covers the cleaner’s waiting time.brbrThank you for your understanding and cooperation -we truly appreciate it and look forward to hosting you!

Lovely Cozy Home with 2 Bedrooms and 1 Bath

Chicago, Illinois, United States

Bed

Bath

4

Sleeps

$1142.97

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 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.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.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.

Hotel

Plymouth Collection: 4BD 3BA with Rooftop & Lobby

Chicago, Illinois, United States

4

Bed

Bath

8

Sleeps

$874.63

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.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.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.

Hotel

Plymouth Collection: 3BD 2BA with Gym & Rooftop

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1081.03

Huge, 2500 sqft Condo in Chicago's most Exciting, Safe, and Historic Neighborhood: Old Town. This is a Private, Full Floor Apartment with 11 foot high ceilings. Located on a Boutique and Restaurant-Lined Street (Wells St) in the Heart of all the Action. Walk to some of the city's best-loved Restaurants, Clubs, Pubs, Parks, Boutiques, and Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc. Grocery Store just a short walk away. Parking for 1 car includedbrbrWe offer a quick, in-person check-in. After that, we're available as needed for any questions or recommendations.

Lovely 4 Bedroom Spot located in Charming Old Town

Chicago, Illinois, United States

Bed

Bath

Sleeps

$1313.66

Welcome to The Luxurious Suite, your premier group getaway in Downtown Chicago’s South Loop!brPerfect for business groups, large families, and friends visiting McCormick Place, this 2,800 sq ft modern loft-style apartment comfortably sleeps up to 12 guests.brbrThis 6-bedroom, 3-bathroom luxury loft blends industrial charm and modern finishes, designed with the comfort of large groups in mind.brbr❤ Prime Location on Michigan AvenuebrbrWhether you’re here for a conference, exploring downtown, or just relaxing in style, the Michigan Suite is the perfect blend of convenience, comfort, and class.brbrBedroom Layout:br- 6 Queen size beds.br- Fresh linens, plush bedding, and blackout curtainsbr- Smart TVs in every bedroombrbrKitchen & Living:br- Stainless steel appliancesbr- Keurig coffee maker + tea stationbr- Cookware, utensils, and essentialsbr- Large dining table for group mealsbr- Oversized sectional sofa + board gamesbrbrNearby Landmarks:br- McCormick Place Convention Center – 9 min walkbr- Soldier Field – 5 min drive / 20 min walkbr- Museum Campus (Field, Shedd, Adler) – 7 min drivebr- Grant Park & Lakefront Trail – 5 min drivebr- Downtown / The Loop – 8 min Uberbr- Subway Station (Green/Red Line) – 6 min walkbr- Wintrust Arena, Chinatown, Roosevelt Collection Shops – all nearby!brbr✔ Amenities at a Glance:br 6 Bedrooms, Sleeps 12br• 3 Full Bathroomsbr• Superfast Wi-Fibr• Smart TVs in every roombr• Central A/C + Heatingbr• In-unit Washer & Dryerbr• Gym in Buildingbr• 24/7 Securitybr• Optional Parking ($30/day)br• EV Charging Availablebr• Family Friendly: Pack n’ Play, High Chair (upon request)br• Professionally Cleaned & Stockedbr• Coffee, Tea, Essentials IncludedbrbrThis property is top-rated for group stays in Chicago and offers exceptional value and location. Whether you're in town for business, events, or leisure, you'll enjoy the privacy, size, and comfort our Michigan Suite delivers.brbr✉ Contact us for longer stays or special requests – we’d love to host you!brbr FAQsbrQ:Check-in / Check-outbrA: Check-in: 4:00 PM | Check-out: 11:00 AMbrEarly check-in/late check-out may be available for an additional fee.brbrQ: Parking InfobrA: Optional Parking – $30/daybrParking in Chicago can be tough to find, so we're happy to offer our guests the convenience of optional parking for $30 per day. brbrIt works just like parking at a shopping mall —there are no reserved or dedicated spots, and parking is first come, first served. You’ll be able to park in any open space available when you arrive.brbrIf you're planning to bring a car, let us know in advance and we’ll guide you through the process to make things easy. brbrQ: Is the area safe brA: Absolutely! The building features 2-shift security and is located in a vibrant, walkable area with restaurants, cafes, and event venues.brbrQ: What’s provided brA: Fresh towels, linens, hairdryer, iron, shampoo, body wash, toothbrushes, toothpaste, and a starter pack of toiletries are all included.brbrQ: Are the beds comfortable brA: Extremely. Guests often ask where we bought our mattresses — they're that good!brbrQ: Is it clean brA: We take pride in a spotless, professionally cleaned unit between each stay.

Luxury 6BR Spacious Loft with Skyline Views Near McCormick Place & Soldier Field

Chicago, Illinois, United States

6

Bed