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Condo vacation rentals in Chicago Loop

Find and book unique condos on Airbnb

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Popular amenities for Chicago Loop condo rentals

Weekly condo rentals

Top guest favorite
Condo in West Loop
5 out of 5 average rating, 30 reviews

Private rooftop | Breathtaking skyline view

BrianRating, 5 stars2 weeks ago
The space was exactly as advertised, roof top patio was awesome. Location was great and Anna was easy to work with. Definitely recommend, we would stay here again.
Guest favorite
A spacious kitchen is equipped with modern appliances and sleek cabinetry. A large white dining table with black chairs is prominently featured, allowing ample seating. Bright overhead lights illuminate the area, while a doorway leads to a living space beyond.
Condo in River North
5 out of 5 average rating, 19 reviews

Gold Coast/Downtown Hideaway

JohnRating, 5 stars2 months ago
These hosts were excellent. Our family of four enjoyed our three nights immensely. Quiet neighborhood. Close to everything. Hosts were responsive, accurate in their description of the apartment, and pleasant folks. Highly recommend this place.
Top guest favorite
A spacious rooftop deck features a charcoal grill alongside a comfortable seating area. A sectional sofa is set on a patterned rug, surrounded by greenery hanging from the trellis above. The deck's wood-planked flooring enhances the outdoor living experience with views of the surrounding city.
Condo in West Loop
5 out of 5 average rating, 57 reviews

Sun-Soaked West Loop Penthouse - Private Rooftop

KendallRating, 5 stars2 weeks ago
We stayed at Reggie’s place for Memorial Day weekend as a family of 5 (2 Adults, a 4 year old, twin 2 year olds). Reggie was very easy to communicate with from the first booking request. He let us know that there couldn’t be loud noise after 10 am (no issue for us) before confirming the booking. We had no issues with check in or check out, and he was responsive to every question. The location was perfect and walkable to so many things, including all the restaurants in west loop and worked well for our family and dog.
Guest favorite
An inviting outdoor patio area features comfortable seating on a sectional sofa and two additional chairs. String lights hang above, illuminating the space. A rectangular coffee table sits on a green rug, surrounded by lush greenery, creating a relaxing atmosphere for casual gatherings.
Condo in West Loop
4.9 out of 5 average rating, 86 reviews

Welcome to the Chi! Close to Downtown

MartelRating, 5 stars1 month ago
Enjoyed my stay at Jasna's. Great unit in a great location
Superhost
A functional kitchen features warm wood cabinetry and modern stainless-steel appliances. A large island with a stainless-steel surface provides additional workspace, while a subtle area rug adds comfort. Natural light is provided by the window above the sink, illuminating the elegant granite countertops.
Condo in West Town
4.89 out of 5 average rating, 37 reviews

Rustic Cozy Haven in West Town

KatieRating, 5 stars1 week ago
Yara was a great host! Very responsive, clear instructions to get into the Airbnb. The place was spacious and very clean, looked exactly like the photos. Would definitely stay there again!
Guest favorite
An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.
Condo in Woodlawn
5 out of 5 average rating, 39 reviews

University of Chicago Condo-Upgraded and Spacious

TiaraRating, 5 stars4 weeks ago
I had a wonderful stay! The place was exactly as described—clean, cozy, and in a great location. The host was super friendly and responsive, which made the whole experience smooth and welcoming. I especially appreciated the thoughtful touches like I’d definitely stay here again and highly recommend it to others!
Top guest favorite
A coffee bar area features a sleek coffee machine and a pod system, neatly arranged on a granite countertop. Disposable cups and a variety of coffee pods are organized in trays, providing convenience for guests. Natural wood cabinetry complements the setup.
Condo in Near West Side
5 out of 5 average rating, 28 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars6 days ago
Thomas is an amazing host! He was very proactive in communicating right from the start of the trip ,was very welcoming and warm. This Airbnb house is spic and span. It is very clean , beautifully decorated and has everything you need to be comfortable in a home. The Kitchen is stocked with all vessels , has basic pantry supplies and has a gas for cooking warm meals. Thomas and his wife were also very thoughtful and considerate and left us a basket full of snacks and coffee pods - that was a really sweet gesture from their end.The coat closet has umbrellas , incase you need one , which I thought was very considerate as well. Thomas also regularly checked in on us to ensure we had a smooth stay - his check in and checkout instructions were uber clear and made it possible to check in and check out without any hassles. There is a starbucks and a bunch of small restaurants on a 10 - 13 min walk from the house.Overall , I would highly recommend his house to other guests.
Top guest favorite
A black metal staircase leads to a second-floor apartment, framed by greenery and soft lighting. A spacious outdoor patio is visible, furnished with chairs and a dining table, while large glass doors suggest a bright interior. The surrounding area is neatly paved, enhancing accessibility.
Condo in Roscoe Village
5 out of 5 average rating, 71 reviews

Sunny Treetop Oasis in Roscoe Village - 1BR/1BA

KathleenRating, 5 stars1 month ago
I had an amazing stay. This place is cute and cozy. Exceeded my expectations. The inside is newly renovated and modern. Very, very clean. Nice little balcony and table if you want to eat outside. Neighborhood is calm, quiet, and I felt safe taking walks around Roscoe Village. Accurate description, great communication before, during, and after my stay. Detailed information in the email and guest guide were helpful. I got to meet Daran and his dog. Both were very friendly. A++ I Highly recommend!!! If I'm ever in the area, I will definitely stay again.

Pet-friendly condo rentals

Superhost
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in Pilsen Historic District
4.84 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

HasimeRating, 5 stars1 month ago
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.
Guest favorite
A cozy living area features a gray sectional sofa adorned with patterned cushions. A white coffee table sits on a soft area rug, while a vase of flowers adds a touch of elegance. An open kitchen with wooden cabinets is visible in the background.
Condo in Bridgeport
4.95 out of 5 average rating, 131 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

MarioRating, 5 stars2 weeks ago
I stayed at John’s Airbnb during my trip to Chicago, and I honestly couldn’t have asked for a better spot—especially being right in the heart of Chinatown. The place was spotless, super cozy, and had everything I needed for a comfortable stay. You can tell John takes pride in keeping it clean and well-stocked, which I really appreciated. What made it even better was the location. Chinatown in Chicago is such a vibe—full of culture, energy, and some of the best (and most affordable) eats in the city. If you’re a foodie like me, you’ll love exploring all the spots nearby. One place I highly recommend is Hing Kee. Their hand-pulled noodles and dumplings are on point—fresh, flavorful, and easy on the wallet. If you’re looking for a clean, convenient, and authentic Chicago experience, especially in Chinatown, John’s place is the move. I’d definitely stay here again.
Top guest favorite
The entryway features a wooden door with a glass panel, leading to a cozy living space. Gray walls complement modern kitchen cabinetry and stainless steel appliances. A comfortable sofa, adorned with white pillows and a soft throw blanket, sits invitingly in the foreground. Decorative elements add character.
Condo in Lake View
4.99 out of 5 average rating, 177 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

BenjaminRating, 5 stars1 day ago
My dad and I were on a baseball road trip and this was a perfect place for a cubs game! About a 15 minute walk. Will was responsive and friendly, and the place might have been one of the coolest bnbs. Such a fun and relaxing spot. Would easily stay again!
Guest favorite
A bright living area is illustrated with large windows allowing natural light to fill the space. A comfortable beige sectional sofa provides seating, while a wooden coffee table sits on an area rug. A desk with modern design and a chair are present, enhancing the workspace.
Condo in West Town
4.92 out of 5 average rating, 120 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

RachaelRating, 5 stars1 week ago
Our stay was fantastic. We have three children and everyone was comfortable. The location was perfect, the hosts were clear communicators and quick to respond. We would stay here again in a heartbeat.
Guest favorite
An open patio space features a light blue sofa adorned with decorative pillows in vibrant colors. A round wooden table sits nearby, complemented by a stylish green side table. Soft lighting from large windows enhances the cozy atmosphere of the room.
Condo in Pilsen Historic District
4.94 out of 5 average rating, 126 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 stars4 days ago
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!
Superhost
A modern kitchen area features white cabinetry and a central island equipped with a sink and stools. Stainless steel appliances are visible alongside a decorative backsplash. Natural light fills the space through overhead lighting and a nearby entryway.
Condo in Chicago
4.87 out of 5 average rating, 119 reviews

Unique 2BR/2BA FREE Street Parking/WI-FI Near DT

AlfredoRating, 5 stars2 weeks ago
Everything went well. Place was very nice and the host was very responsive when I needed help and accommodative as well. Highly recommend if needed a place near downtown.
Top guest favorite
Condo in Logan Square
4.92 out of 5 average rating, 347 reviews

Susie's Space. 2BR easy parking & pet friendly

PennyRating, 5 stars3 weeks ago
Great neighbourhood! Susan was very communicative and a great host. Highly recommend.
Superhost
The spacious living area features high ceilings and large windows, allowing natural light to fill the room. A wooden dining table is accompanied by several chairs, while a sleek kitchen is visible in the background, highlighted by modern appliances and cabinetry.
Condo in Lincoln Park
4.79 out of 5 average rating, 224 reviews

Modern Luxury In Old Town - Sleeps 4

AlexanderRating, 5 stars4 weeks ago
I had a great stay! The Airbnb was easy to get to and in a fantastic location within walking distance to restaurants, bars, gyms, and public transportation. The space was very clean and well-maintained. Would definitely recommend and stay here again!

Condo rentals with a pool

Guest favorite
An outdoor pool area is shown, featuring a clear blue pool surrounded by lounge chairs. Trees provide a touch of greenery, while a modern glass structure offers shaded seating. Sunshine reflects off the water, creating a bright and inviting atmosphere.
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

AaronRating, 5 stars1 month ago
I would highly recommend Michelle's listing! The listing is spacious and perfect for a couple or small family (we had our <1 year old). Michelle is communicative, all the instructions are clear, and the location is convenient.
Guest favorite
Condo in Evanston
4.95 out of 5 average rating, 107 reviews

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

RemiRating, 5 stars1 month ago
Our Stay at The Bliss of Evanston was great. The host is very responsive and was very accommodating of our requests. The location and view can not be beat.
A serene bedroom is illuminated by soft purple lighting. A spacious bed with a polka dot blanket is centered in the room. Floor-to-ceiling glass doors reveal a view of a vibrant city skyline at night, with city lights twinkling in the background.
Condo in The Loop
4.4 out of 5 average rating, 10 reviews

voco: Balcony & City View

BrookeRating, 5 stars3 weeks ago
Our stay here worked out perfectly. The host was nice, and the location was centrally located to great shopping and restaurants. Very private and safe. The view at night was beautiful.
A cozy living area is highlighted by a wood-burning fireplace, where a warm fire flickers. A sleek coffee table sits in front of a comfortable sectional sofa, complemented by a textured area rug. Two glasses of wine rest atop the table, adding a touch of relaxation.
Condo in Lombard
4.84 out of 5 average rating, 56 reviews

Smoke & Pet Free, Washer Dryer, Fireplace, Balcony

LelandRating, 5 stars5 months ago
Briana was responsive before, during and immediately after our stay, always seeking to ensure our comfort and satisfaction. We would have no reservations about staying with them again if they have an opening during a future visit to the area.
An outdoor pool area features a clear, blue body of water surrounded by lounge chairs. Lush greenery is placed in large planters along the perimeter, with a backdrop of modern high-rise buildings and a cloudy sky.
Condo in Magnificent Mile
4.33 out of 5 average rating, 9 reviews

30 E. Huron #2603 Private Residence

Diego HernanRating, 5 stars25 months ago
Incredible experience. Kevin was very nice and helped us with everything. I would go back again to this amazing apartment and great location.
Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village
4.94 out of 5 average rating, 85 reviews

Just remodeled apartment close to airport and mall

MeagRating, 5 stars2 months ago
I am incredibly particular with places I stay. This place was simple, very clean, had everything you would need to be comfortable. Bed was great! ⭐️ ⭐️ ⭐️ ⭐️ ⭐️
Guest favorite
An outdoor swimming pool is surrounded by lounge chairs, offering a relaxing space. Trees are strategically placed around the area, and large glass walls provide views to the inside. Sunlight reflects off the water, enhancing the serene setting.
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

FeiRating, 5 stars2 days ago
You can walk to Northwestern University, and the surrounding environment is clean and comfortable.The house is fully furnished, I love cooking in the kitchen.Our whole family had a great week here.Would stay again.
Guest favorite
Condo in Evanston
4.96 out of 5 average rating, 100 reviews

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

AileenRating, 5 stars1 week ago
Space was clean and in a charming, walkable city. The view in the living room was beautiful. The neighbors were quiet. The coffee in the condo and in the lounge was surprisingly delightful. Our group of friends had a great time, and this would be a perfect place for a family.

Quick stats about condo rentals in Chicago Loop

  • Total rentals

    50 properties

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

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