Vacation Rentals By Owner In Chicago, IL

$1266.73

Luxury Fulton Market Penthouse Amazing City Views

Chicago, Illinois, United States

Summary:brbrNEW PENTHOUSE LOFT IN FULTON MARKET!brbrbrbrEnjoy your own private luxury loft in Chicago's bustling Fulton Market-the city's center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse features 12 foot open lofted ceilings, a personal home gym w/ Peleton+, free onsite garage parking, 4 bedrooms/4.5 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!brbrbrbrThe Space:brbrLocated on the top floor of a boutique apartment building with views overlooking the city and just steps from Fulton Market, your luxurious penthouse sleeps 16+ people and is perfectly situated for large groups, families, events, work trips, and curated dinners. Everything flows around the spacious and open living room and chef's kitchen, add the floor to ceiling windows and the space becomes a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combo is decorated in modern contemporary art and features a large sectional, accent chairs, dining table for 10+ people, smart TV (Netflix, Hulu, Prime, etc. compatible) and record player for entertainment.brbrbrbrAttached to the dining room, the chef's kitchen is outfitted with gas-powered Viking ranges, an oven, restaurant sized refrigerator and freezer, plenty of cabinetry, plates, cups, and cutlery in addition to state-of-the-art kitchen appliances including a Nespresso coffee maker, amongst others.brbrbrbrIn addition, enjoy your own private workout room featuring Peleton+, yoga mats, exercise bands, and coffee nook with table and chairs.brbrbrbrThis one of a kind loft comfortably sleeps 16+ people and has 4 bedrooms and 4.5 bathrooms. The main bedroom with a king bed, full bath, outfitted with a relaxing jacuzzi hot tub and waterfall shower. Two additional bedrooms feature two queen beds per room, each with private bathrooms. The fourth and final bedroom sleeps 4 additional people, with two side-by-side enlarged stacked bunk beds with queen size mattresses on the bottom and full size mattresses on top, comfortable for both children and adults. Each bedroom has its own full private bathroom.brbrbrbrSleeping arrangements/room layout:brbrMain bedroom (bedroom 1): King Bed, private bathroom with jacuzzi and showerbrbrBedroom 2: Two queen beds, private bathroom with tub and shower brbrBedroom 3: Two queen beds, private bathroom with tub and showerbrbrBedroom 4: Two full-over-queen bunk bed sets, private bathroom with tub and showerbrbrbrbrWe provide one dedicated parking space in the building garage. There is free street parking directly in front of the building should you need more parking.brbrbrbrOur units are made up fresh before each guest and their group arrives. Our cleaning services that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is striped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may 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, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrThe Neighborhood:brbrNearby Fulton Market has a cool industrial vibe that bursts with activity, thanks to tons of trendy restaurants and bars that have taken over the old warehouse spaces. Between meals, you can explore the West Loop's art galleries, cool shops, and boutique hotels. Check out the year-round Randolph Street Market for unusual vintage and antique finds. In the summer, the market heads outdoors with live music and pop-up bars.brbrbrbrGetting Around:brbrCovered garage parking (1 spot) included in rental. Central access to the CTA (Blue Line 1 block away, Pink and Green Lines 5 blocks away) and Metra lines (rail). Heavy UBER/Lyft coverage locally. Divvy bikes and Lyft scooters readily available nearby.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.

4

Bed

4

Bath

16

Sleeps

$424.94

/ Nightly

Hotel

1BR King Suite w/ Kitchenette | 4mi to Scenic Riverfront Park

Chicago, Illinois, United States

Experience the heart of River North, ideal for families, pets, and business. Steps from the Riverwalk and Magnificent Mile, you’ll enjoy world-class dining and shopping. Iconic sites like Millennium Park and Willis Tower are within a mile. With easy airport access and stunning city views, this is the ultimate home base for exploring Chicago. Perfect for extended stays—book your urban escape now!brbrThis listing is for a room within a hotel.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

1

Bed

1

Bath

4

Sleeps

$487.13

/ Nightly

Hotel

Elevated City View King Suite: Kitchenette & Pool | 1 mi to Performing Arts Ctr

Chicago, Illinois, United States

Experience the heart of River North, ideal for families, pets, and business. Steps from the Riverwalk and Magnificent Mile, you’ll enjoy world-class dining and shopping. Iconic sites like Millennium Park and Willis Tower are within a mile. With easy airport access and stunning city views, this is the ultimate home base for exploring Chicago. Perfect for extended stays—book your urban escape now!brbrThis listing is for a room within a hotel.brbr✦ Your room is 450 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

1

Bed

1

Bath

4

Sleeps

$341.6

/ Nightly

Hotel

Studio w/ King Bed & Kitchenette; Free Hot Breakfast | 1 mi to Tanger Outlets

Chicago, Illinois, United States

Experience the heart of River North, ideal for families, pets, and business. Steps from the Riverwalk and Magnificent Mile, you’ll enjoy world-class dining and shopping. Iconic sites like Millennium Park and Willis Tower are within a mile. With easy airport access and stunning city views, this is the ultimate home base for exploring Chicago. Perfect for extended stays—book your urban escape now!brbrThis listing is for a room within a hotel.brbr✦ Your room is 350 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

1

Bed

1

Bath

4

Sleeps

$343.94

/ Nightly

Hotel

Stylish King Studio Escape | Skyline View & Gym | 1 mi Convention Center

Chicago, Illinois, United States

Experience the heart of River North, ideal for families, pets, and business. Steps from the Riverwalk and Magnificent Mile, you’ll enjoy world-class dining and shopping. Iconic sites like Millennium Park and Willis Tower are within a mile. With easy airport access and stunning city views, this is the ultimate home base for exploring Chicago. Perfect for extended stays—book your urban escape now!brbrThis listing is for a room within a hotel.brbr✦ Your room is 350 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

Bed

Bath

Sleeps

$311.11

/ Nightly

Hotel

Studio w/ Queen Bed & Kitchenette; Free Hot Breakfast | 1 mi to Tanger Outlets

Chicago, Illinois, United States

Located in the vibrant River North neighborhood, this modern suite-style hotel offers spacious accommodations ideal for extended stays. Just minutes from the Magnificent Mile, Navy Pier, and Millennium Park, it provides easy access to Chicago’s top attractions and dining options.brbrThis listing is for a room within a hotel.brbr✦ Your room is 346 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

Bed

Bath

Sleeps

$332.24

/ Nightly

Hotel

Stylish Suite w/ City View | 4 mi to Scenic Riverfront Park

Chicago, Illinois, United States

Experience the heart of River North, ideal for families, pets, and business. Steps from the Riverwalk and Magnificent Mile, you’ll enjoy world-class dining and shopping. Iconic sites like Millennium Park and Willis Tower are within a mile. With easy airport access and stunning city views, this is the ultimate home base for exploring Chicago. Perfect for extended stays—book your urban escape now!brbrThis listing is for a room within a hotel.brbr✦ Your room is 346 sq. ft, equipped with complimentary toiletries, high definition 49-inch TV, available with Premium cable, and Standard cable.brbr✦ Cleaning services are available upon request (additional fee may vary)brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 03:00 pm to 02:00 am.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Paid parking lot – 1 space(s), available for $67.63 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $75.00. Max 2 Dogs/Cats Only | Up to 25lbs per petbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A fee will be assessed for smoking in a non-smoking room. Please ask the Front Desk for locations of designated outdoor smoking areas.brbr✦ Free buffet breakfast available 6:00 AM to 9:00 AM on weekdays and 7:00 AM to 10:00 AM on weekends.

1

Bed

1

Bath

4

Sleeps

$326.33

/ Nightly

Apartment

1R - ❤️ Low Prices! Stylish 2BR Apartment in Logan Square!

Chicago, Illinois, United States

pWelcome to Chicago!/pbrbrpbr/pbrbrpOur 2-bedroom/1 bathroom apartment is perfect for getaway to Chicago. It's professionally designed with modern furniture that gives welcome feeling! We're located in Trendy Logan Square Designated parking spot is NOT available, but there is plenty of street parking available.-The entire condo is for your own use. /pbrbrpbr/pbrbrpIlluminated by sunny natural light, our 1BR features Queen-size bed, premium linens, and plenty of closet space so you can unpack and forget about your suitcase for a while. Enjoy the privacy of your own room, with doors that close and independently controlled air-conditioning units. The apartment includes one full bathroom, with a shower, sink, and toilet. We’re all about helping you look (and smell) your best, so we provide shampoo, conditioner, and body wash in addition to hand soap and fluffy towels. Trust us when we say there’s no better way to warm up after a Windy City walk than a hot shower! There’s ample space for guests to relax on the sofa and watch on a large flat-screen TV. Like the rest of the unit, you’ll live it up in luxury among hardwood floors and contemporary decor. The entire place has free, fast WiFi and Chicago sunshine streaming in through the windows./pbrbrpbr/pbrbrpWhether you’re craving a home-cooked meal or just somewhere to put the box of deep-dish, our kitchen is fully stocked with cookware, dishes, utensils, and has swanky granite countertops. Appliances include a full-sized fridge and freezer, gas stove, oven, microwave, toaster, and coffee maker. The only things missing are your favorite farmer’s market finds!!/p

2

Bed

1

Bath

4

Sleeps

$299.07

/ Nightly

Apartment

Spacious 3-bedroom Comfort Urban Chicago loft house

Chicago, Illinois, United States

Your cozy getaway awaits in Chicago at this marvelous apartment. With three bedrooms featuring a queen, full, and twin bed, there’s plenty of space for everyone. Two bathrooms add convenience, while the living room offers a comfy sofa bed for extra guests. Whether you’re relaxing indoors or exploring the city, this perfect spot provides a wonderful base for your adventures. We hope you'll enjoy your stay at our apartment.

3

Bed

2

Bath

6

Sleeps

$220.39

/ Nightly

Apartment

Chic 2-bedroom apartment w/free parking, quiet Bucktown, Walker/Biker paradise

Chicago, Illinois, United States

Your home away from home in Chicago with 2 lovely bedrooms. This terrific apartment features a queen bed and a full bed, perfect for a soothing night's sleep. Enjoy the convenience of a fully equipped kitchen, a cozy living room, and a bonus office space with a comfy murphy bed. With amenities like a washing machine, AC, and WiFi, guests will have everything they need for a relaxing stay. Book now and enjoy everything this apartment has to offer.

Bed

Bath

Sleeps

$538.31

/ Nightly

Private Vacation Home

Spacious 2BR Unit with Skyline View Near McCormick Place & Soldier Field

Chicago, Illinois, United States

Welcome and Experience modern comfort just minutes from downtown. Our 2-bedroom, 2-bath suite features city views, high ceilings, a full kitchen, EV charging, fast Wi-Fi, gym access, and sleeps 8 comfortably. Walk to McCormick Place, Museum Campus, and great eats. Optional parking available. Professionally cleaned & fully stocked. Perfect for families, groups, or event stays!brbrMessage us for special rates or long stays!brYour perfect Chicago stay starts here.brbrOur space combines urban elegance with homely charm. Featuring high ceilings, tall windows, and custom furnishings, this apartment gives you all the vibes of downtown life—with extra comfort.brbrSleeping arrangements:br2 Queen beds with fresh linens br1 Comfy sofa bedbr1 Queen air mattress (set up upon request)brbrAmenities you’ll love:brFully equipped kitchenbrCentral AC & HeatingbrLightning-fast Wi-Fibr4K Smart TV with NetflixbrIn-unit washer & dryerbrFitness center accessbrElevator buildingbrEV charging stationsbrbrPrime Location Perks:br7-min walk to McCormick Placebr5–10 min Uber to Soldier Field, Museum Campus, Grant Park & DowntownbrSurrounded by top restaurants, bars & cafés brWalkscore: 92brbrYou’ll love the balance of convenience, modern style, and local flair this suite offers.brbrGuests enjoy private access to:brEntire 2BR/2BA apartmentbrFitness room (2nd floor)brLaundry room (same floor)brOptional secured parking ($30/day)br24/7 security-monitored buildingbrbrSelf check-in makes arrival easy and stress-free.brbrMessage us for exclusive rates, group inquiries, or special requests!brOur unit is professionally cleaned between each stay brWe provide:br- Fresh towels & linens br- Shampoo, conditioner, soap br- Individually wrapped toothbrushes br- Starter paper products & kitchen basics brbrHot water is supplied by an 80-gallon tank—please use mindfully brOn-site parking available for just $30/day—a rare gem in downtown Chicago!brCheck-in: 4 PM | Check-out: 11 AM | Early/Late available for a feebrbrWhether you’re visiting for a convention, celebration, or city adventure—we’re ready to host you with care .

2

Bed

2

Bath

8

Sleeps

$647.18

/ Nightly

Apartment

Stylish 2-Bedroom Retreat with Parking and Balcony

Chicago, Illinois, United States

Summary:brbrExperience upscale city living with TheDreamRentals in this stylish 2-bedroom, 2-bath Airbnb in Chicago’s Tri-Taylor neighborhood. brbrbrbr- Modern interiors with designer finishes brbr- Spacious bedrooms with queen beds brbr- Fully equipped gourmet kitchen brbr- Near the United Center brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrAs you step inside, be prepared to be awed by the contemporary design and impeccable attention to detail. The open-concept living area welcomes you with its abundance of natural light and stylish furnishings. The expansive windows not only fill the space with warmth and brightness but also offer breathtaking views of the surrounding cityscape. brbrbrbrComfortable Accommodation: brbr- 2 spacious bedrooms: One king and one queen brbr- Master bedroom features an ensuite bathroom brbr- Second bathroom nearby brbrbrbrInterior Feeling: brbr- High ceilings and large windows brbr- Contemporary design with stylish furnishings brbr- Plush sofa for relaxation brbr- Large flat-screen TV with cable channels brbrbrbrOutdoor Bliss: brbr- Private balcony with city views brbr- Perfect for enjoying fresh air brbr- One free garage spot includedbrbrbrbrDelightful Dining: brbr- Fully equipped gourmet kitchen brbr- Sleek countertops and modern appliances brbr- Ample storage space brbrbrbrProfessional Cleaning: brbr- Impeccable attention to detail in cleanliness brbr- Premium bath products in bathrooms brbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrGuests will have access to the entire unit.brbrbrbrThe Neighborhood:brbrIt is located in Chicago’s Tri-Taylor neighborhood, part of the broader Near West Side community. This area is just west of the Illinois Medical District and close to the University of Illinois at Chicago (UIC), making it a popular spot for medical professionals, students, and long-time residents alike. The neighborhood features a mix of historic brick two- and three-flats, quiet tree-lined streets, and newer developments. Tri-Taylor is known for its proximity to the historic Little Italy district along Taylor Street, home to old-school Italian restaurants, cafés, and bakeries. The area maintains a down-to-earth, residential feel with an increasing wave of investment and redevelopment, blending long-standing community roots with a growing influx of young professionals and families.brbrbrbrGetting Around:brbrPublic transit near is convenient and well-connected, centered around the CTA Pink Line’s Polk Station, just a block away. This line offers quick access to downtown Chicago (the Loop) and operates frequently from early morning to late night. Several CTA bus routes, including the #7 Harrison, #157 Streeterville/Taylor, and #12 Roosevelt, also run nearby, providing easy east-west access and connections to other train lines and neighborhoods. The area is highly walkable and transit-friendly, making it ideal for commuting to the Illinois Medical District, UIC, or downtown.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 penthouse. Please smoke outside.brbrbrbrPet Policy: We adore pets, but unfortunately, the penthouse 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.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the penthouse 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 $500 will be required before check in.brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrDue to a building requirement, primary guest must be 25 years or older to book!brbrbrbrShared Housing Unit Operation License Number: 2823378 brbrRegistration number: R25000130964brbrbrbrInteraction with Guests:brbrPrivacy 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.brbrbrbrOur goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.

Bed

Bath

Sleeps

$293.06

/ Nightly

Apartment

A 3-bedroom, 2-bathroom residence that provides ample space and comfort.

Chicago, Illinois, United States

Your Chicago adventure begins at this 3-bedroom apartment. Step into a nice and serene space where guests can relax after a day of exploring. The apartment features two bathrooms, making it easy for everyone to get ready comfortably. With heating and air conditioning, the temperature stays just right no matter the season. An adorable living area invites guests to unwind and enjoy some downtime. Whether you’re here for work or leisure, this spot offers a peaceful retreat in the heart of the city. We look forward to hosting you at our place.

Bed

Bath

Sleeps

$1018.56

/ Nightly

Apartment

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, Illinois, United States

Perfectly located in the heart of Chicago in the River North neighborhood.brbrYou will experience Chicago easily from here!br• Surrounded by world class shopping on the Magnificent Milebr• In the heart of big-city nightlife and the city's best diningbr• Walk to Lake Michigan and Navy Pierbr• Steps from the local trains and buses to go anywhere in the citybrbrThis is an intimate building with no common areas which will reduce COVID risk.brbrSpacious open layout perfect for large groups, friends, and family. Also featuring:br• Fully stocked kitchen includes coffee machine, new appliances, and everything to have a home-cooked gourmet mealbr• Gameroom stocked with board games, poker chips, and a shuffleboard tablebr• Local artists exhibilition featuring Chicago landmarks, interesting local destinations, and pieces that make you feel the essence of Chicago!br• Equipped with high speed 150mbps wifi and large computer monitor (upon request)brbrImmediately outside the condo:br• Attached gated parking for 1 vehiclebr• Private large patio with a Weber Grill for the outdoor chefsbr• Keyless entry for your security and convenience

3

Bed

2

Bath

10

Sleeps

$180.37

/ Nightly

Apartment

3-bedroom apartment in phenomenal Chicago with WiFi, AC

Chicago, Illinois, United States

This awesome apartment in Chicago offers 3 cozy bedrooms - one with a queen bed, one with a twin bed, and a third with a comfy futon. With 2 bathrooms equipped with a hair dryer, bathtub, and shower, guests will feel right at home. Enjoy the welcoming atmosphere of this property, complete with AC, heating, WiFi, a washing machine, and an iron. Experience what Chicago has to offer with a stay at our apartment.

Bed

Bath

Sleeps

$184.25

/ Nightly

Private Vacation Home

3BR Monthly Rental Near Midway Airport/Downtown

Chicago, Illinois, United States

Summary:brbrDiscover a cozy Chicago retreat in this charming single-level house, ideal for families and small groups. Featuring three bedrooms, a fully-equipped kitchen, and a comfortable living area, it's designed for a relaxing stay. Conveniently located near Giordano's and Midway Airport, with easy access to public transport and downtown Chicago.brbrbrbrThe Space:brbrThis home offers a comfortable and practical layout, ideal for families, small groups, or business travelers. The space features three comfortable beds and one full bathroom, providing a relaxing setup for both short and extended stays.brbrbrbrThe living area is bright and inviting, with cozy seating perfect for unwinding after a day of exploring or gathering with your group. The fully equipped kitchen includes essential cookware, dishes, and appliances, making it easy to prepare meals or enjoy coffee at home.brbrbrbrEach sleeping area is thoughtfully designed with comfort in mind, featuring fresh linens, pillows, and storage to help you settle in with ease. The bathroom is clean and well-maintained, stocked with towels and basic essentials for your stay.brbrbrbrAdditional amenities such as high-speed Wi-Fi, a smart TV, climate control, and convenient self check-in ensure a smooth and stress-free experience. Located just 9 minutes from Midway Airport, this home is especially convenient for travelers seeking quick airport access without sacrificing comfort.brbrbrbrGuest Access:brbrYou have private access, including a private entrance, to the entire 3BR portion of the home. The basement level portion has a separate entrance and is rented by long-term tenants.brbrbrbrThe Neighborhood:brbrThe home is located in a convenient and residential Chicago neighborhood just minutes from Midway International Airport. The area offers a relaxed, local feel with easy access to restaurants, coffee shops, grocery stores, and everyday essentials. Guests will appreciate the quiet streets while still being close to major roads and public transportation, making it easy to get around the city. Whether you’re heading downtown, catching a flight, or exploring nearby neighborhoods, this location provides a great balance of comfort, accessibility, and convenience.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 house. Please smoke outside.brbrbrbrPet Policy: pets allowedbrbrbrbrQuiet 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.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.brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.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.brbrbrbrInteraction 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.brbrbrbrEmergency Assistance: In case of any emergencies or urgent matters, you'll find contact information for our responsive team in the provided house manual.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

$230.19

/ Nightly

Apartment

The Avondale Lower Level

Chicago, Illinois, United States

Check out my basement apartment in Irving Park. The property is right off of Addison Street. Free parking and close to the 90/94 expressway. The Addison Blue Line subway is a 10 minute walk. brbrBasically a rec space, I rent this out at different times of the year as a convenience to those looking for an alternative to hotels and want to live like a local. I am not part of a property management group, but do love accommodating guests. brbr***This basement unit has low ceilings (not super low, but should be noted)***br***Pets live on the property and next door. Although not excessive, you will hear dogs at times***br***The back yard area is not available for use. brbrAs your host, I will help with any information you may need to make your stay in Chicago a memorable one. If I'm in town and not working I will be able to greet you upon your arrival. However majority of the time I am away, and will provide instructions on entering the unit. brbrYou have 100% Privacy. You will not be sharing this apartment with any one else. brbrThe unit also has a private entrance that only you will use. Plenty of permit parking available in front of the house. I provide the permits. brbrCooking ware provided. brbrA Smart TV is mounted in the living room. You can choose to stream or use antenna tv. There is no cable tv. brbrThe apartment has a full bathroom and laundry room.brbrThe master bedroom has a king bed, dresser, and closet. The second bedroom is smaller and has a full size bed. The entire space fits 4-5 people.

2

Bed

1

Bath

4

Sleeps

$445.94

/ Nightly

Condo

Elegant 3BR/2BA Hyde Park Retreat ~ Private Deck ~ Near UChicago & Lakefront

Chicago, Illinois, United States

Experience the perfect blend of space, comfort, and location in this beautifully appointed 3-bedroom, 2-bath condo in the heart of Hyde Park. Whether you're visiting Chicago for work, family, or a weekend getaway, this inviting home offers everything you need for a memorable stay.brbrThe SpacebrDesigned with both style and functionality in mind, this spacious condo features an open yet cozy layout with distinct living and dining areas—perfect for relaxing, entertaining, or spending quality time together.brbrSleeping & Layout:brbrPrimary Bedroom: King bed + private full bathroom + Twin to King Extendable DaybedbrSecond Bedroom: Queen bedbrThird Bedroom: Two Twin beds (great for kids or extra guests)brOptional sofa/air mattress for additional sleeping spacebrTwo full bathrooms with fresh towels and essential toiletriesbrbrHome Features:brbrBright, airy living room with comfortable seatingbrDedicated dining room—ideal for group meals or game nightsbrFully equipped kitchen with everything you need to cookbrPrivate back deck—perfect for morning coffee or evening unwindingbrHigh-speed Wi-Fi + workspace for remote workbrSmart TV for streaming entertainmentbrIn-unit laundry for added conveniencebrCentral heat & A/C for year-round comfortbrbrLocation – Prime Hyde ParkbrSituated on a quiet, tree-lined street, you’ll be just minutes from some of Chicago’s most beloved destinations:brbrUniversity of Chicago campusbrLake Michigan, beaches, and scenic trailsbrMcCormick Place Convention CenterbrLocal cafés, restaurants, and boutique shopsbrMuseums and cultural landmarksbrQuick and easy access to downtown ChicagobrbrPerfect For:brbrFamilies visiting students or exploring the citybrGroups traveling together who want space and comfort. Business travelers or academics needing longer stays. Anyone looking for a peaceful neighborhood with city accessbrbrGuest AccessbrEnjoy full, private access to the entire condo, including the back deck.brbrWhy You’ll Love ItbrThis home offers the rare combination of generous space, thoughtful amenities, and a prime location. Start your day with coffee on the deck, explore Hyde Park’s charm, and return to a comfortable, relaxing space that truly feels like home.brbrBook your stay today and enjoy Chicago in comfort and style!

3

Bed

2

Bath

11

Sleeps

$813.61

/ Nightly

Private Vacation Home

Wicker Park 4bd/3ba, Steps from CTA, Parking Incl by AllSet Turnover

Chicago, Illinois, United States

**Private Gated Parking for 2 Cars Included brbrYou'll love staying at our beautifully designed duplex up in Wicker Park. Ourbrbrhome has 4 bedrooms, 3 bathrooms, a gourmet kitchen, an entertainer's diningbrbrroom, open modern layout with 2 separate living spaces, plus a large outdoorbrbrpatio. Ideally located on a quiet street near the excitement of Milwaukee Avebrbrand Division Street, you certainly won't run out of things to do! Just stepsbrbrfrom the Blue line and only 15 minutes from the loop. Book today! 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. brbr**House Rules:** brbr brbrPlease respect our home and neighbors. Violations of ANY of the followingbrbrrules may result in fines and/or termination of your reservation without abrbrrefund. brbrbrbr 1. No parties or unapproved guests - Only registered guests may access the property. Parties, gatherings, and group events are strictly prohibited.brbr 2. No additional visitors - Only those listed on the reservation may enter the property. Any additional visitors must be declared and pre-approved.brbr 3. Respect quiet hours - Keep noise levels down, especially between 10:00 PM - 8:00 AM. Failure to respect quiet hours or disturbances from an unauthorized gathering will result in termination of the reservation without refund and may result in additional fines to pay city tickets or HOA fines for violations.brbr 4. Check-out on time - Please vacate the unit and return any issued keys by the agreed check-out time. Late check-outs will incur a $250 fee.brbr 5. No smoking - Smoking of any kind is prohibited inside the unit and on the building premises. Evidence of smoking, including odor, will result in a $500 remediation charge. Local laws also prohibit smoking within 15 feet of any entrance.brbr 6. Lockouts & lost keys - A $150 lockout fee applies per occurrence. Lost keys or remotes will incur a $50 replacement fee each.brbr 7. Lost & found - We are not responsible for lost items. If something is left behind, we will attempt to locate it and ship it at your expense. Please check all drawers and closets before departure.brbrbrbr brbrAdditional Policies:brbrbrbr * Guest verification - To comply with legal and security requirements, you may need to sign a rental agreement, provide a government-issued photo ID, confirm your contact details, and submit a selfie matching your ID.brbr * Guest screening - Guests must have a positive track record on the booking platform and provide details about their stay and the guests traveling with them.brbr * AutoHost verification - We conduct additional screening after booking and reserve the right to decline reservations that do not pass verification.brbrbrbr brbrBy completing your reservation, you agree to ALL policies and rules statedbrbrabove. TAX ID: R24000116181brbrbrbr

4

Bed

3

Bath

7

Sleeps

$1197.3

/ Nightly

Private Vacation Home

Jacuzzi, Movie Theater, Game Room, Gym, Arcade, Backyard, King Ste, Portage Park

Chicago, Illinois, United States

Welcome to Portage Park! This beautifully remodeled 5-bedroom, 3-bathroom luxury style home is spacious 2,200 sq ft retreat designed for families, friends, and large groups of up to 16 guests. With 2 levels of living space, hot tub backyard, fun games, gym and a one of a kind entertainment basement inluding a home theater, game station for kids, game table & arcade machine, King Master with a private string light filled outdoor deck, we have everything you need for a memorable Chicago vacation!brbrBook this one of a kind luxury 5 bedroom home!brbrBedrooms & ComfortbrbrGet ready to relax in style! The master suite features a plush king bed, Smart TV, and a private deck with outdoor seating, glowing string lights, and charming neighborhood views. Two bedrooms feature double queen beds, while two additional bedrooms each offer a queen bed—all with Smart TVs and streaming access for cozy movie nights. With modern décor and space for everyone, you’ll rest easy after days of exploring Chicago.brbrBathroomsbrbrWith three full bathrooms, mornings and evenings are a breeze for large groups. Each bathroom is modern, clean, and designed to keep everyone comfortable and refreshed.brbrEntertainment BasementbrbrThe showstopper of this home is the spacious basement packed with unique amenities! Enjoy your own private movie theater with a projector, large screen, and velvet curtains for a true cinema vibe. Keep the fun going with an arcade machine, game table with board games, and a popcorn machine. There’s even a kids’ corner with climbing games to keep the little ones happy, plus a runway for exercise and a small gym for fitness lovers.brbrBackyard FunbrbrStep outside to the grass backyard, perfect for outdoor fun and relaxation in the steamy hot tub. Challenge friends to cornhole or giant Jenga. Whether it’s family game time or unwinding under the stars, this backyard is made for memories.brbrJacuzzi Hours are 8 am-10pm and it is available from March to December, please do not use the jacuzzi after 10 pm to respect our neighborhood guidelines. We have a fee of $30/day for the jacuzzi use and can share instructions on how to use. brbrPlease let me know if you are interested and how many days you plan on using the jacuzzi.brbrbrHome FeaturesbrbrCentral AC & heating for year-round comfortbrbrWasher & dryer for conveniencebrbrFully remodeled interiors with stylish finishes and modern touchesbrbrSpacious layout across two levelsbrbrLocationbrbrNestled in one of Chicago’s best neighborhoods, this home offers the perfect mix of peace and convenience. You’ll be just minutes from local dining, shopping, and attractions, making it easy to explore the best of the city while enjoying the privacy of a welcoming residential area.brbrThis home isn’t just a place to stay—it’s a place to play, relax, and connect. Whether you’re hosting a family reunion, friends’ trip, or group retreat, this Chicago vacation rental is ready to make your stay unforgettable.brbrRestaurants nearbybrbrTrattoria Porretta Ristorante Pizzeria (322 Feet)brLa Costa (Mexican Seafood) (1.9 Miles)brLatin Patio Restaurant (1.9 Miles)brCentral Gyros (2.0 Miles) brCommunity Tavern (2.0 Miles)brSmakosz (Polish / Pierogi spot) (2.2 Miles) brRoma’s Italian Beef & Sausage (2.2 Miles) brLa Fogata / Fiesta Mexicana (2.6 miles) brMarie’s Pizza & Liquors (2.8 Miles)brbrActivities/Things to do nearbybrbrCragin Park (1.5 Miles)brRiis Park & Riis Natural Area (2.2 Miles)brWrightwood Bungalow Historic District (2.5 Miles)brFalconer Bungalow Historic District (2.7 Miles)brHermosa Bungalow Historic District (3.0 Miles)brBelmont Avenue / Belmont-Central Shopping & br Dining Area (3.2 Miles)brPortage Park (3.3 Miles)brMillennium Park (Downtown) (8-9 Miles)brSkydeck Chicago at Willis Tower (9-10 Miles)brNavy Pier (9-10 Miles)brbrCheck-in, and address details will be sent prior to your arrival.brbrJacuzzi Hours are 8 am-10pm and it is available from March to December, please do not use the jacuzzi after 10 pm to respect our neighborhood guidelines. We have a fee of $30/day for the jacuzzi use and can share instructions on how to use. brbrPlease let me know if you are interested and how many days you plan on using the jacuzzi.brbrNo events or parties brbrQuiet hours are from 9 pm until 7 am.brbrNo pets are allowed.brbrNo smoking or vaping of any kind is allowed inside the house. If this rule is disregarded, we will pursue and charge a $1000 fee to cover costs of additional cleaning and deodorizing services. If smoking occurs inside the home during the stay, there will be a $1000 fine for this violation.

5

Bed

3

Bath

16

Sleeps

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