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Condo holiday rentals in Downtown Chicago

Find and book unique condos on Airbnb

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Popular amenities for Downtown Chicago condo rentals

Weekly condo rentals

Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 50 reviews

Downtown Park Mich Ave Penthouse - Rooftop & Gym

WendiRating, 5 stars3 weeks ago
Loved our stay at this centrally located condo. Building was secure and had great amenities like a gym (which we used) and a rooftop terrace with gorgeous views! The bed was very comfortable and the kitchen was well-stocked. My pup, Charlie, felt right at home too. 🐾 We would definitely stay here again. The hosts were very responsive throughout our stay, as well.
Guest favourite
Condo in Chicago
5 out of 5 average rating, 20 reviews

Gold Coast/Downtown Hideaway

HoldenRating, 5 stars1 week ago
Awesome place to stay at in Chicago! Very close to the “Chicago” red line stop with the “L”. Super thankful to have found this place and booked it!
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 116 reviews

Wrigleyville Inn. Historic Greystone, Free Parking

TeresaRating, 5 stars3 weeks ago
Had a great stay at Peter's apartment even better than photos. 5 minutes walk to red line for downtown. Wrigley field on doorstep good restaurants and bars within walking distance. If we are ever back in Chicago would definitely stay again
Superhost
Condo in Chicago
4.87 out of 5 average rating, 120 reviews

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

MelissaRating, 5 stars4 days ago
Awesome location, near lots of local restaurants, public transit and a major grocery store. China Town is a short bus ride away. The neighborhood itself is awesome, helpful neighbors and very friendly local vendors. The apartment itself is clean, inviting and has everything you could possibly need. Cory and Alexis were very inviting host, quick to respond to my questions and were very informative. I will be keeping this location in mind for my future Chicago travels.
Guest favourite
Condo in Chicago
4.94 out of 5 average rating, 102 reviews

NEW luxury Old Town 1-Bedroom condo

JoniRating, 5 stars1 week ago
We loved staying here during our recent trip to Chicago. We were traveling with two young children, and the space was perfect for us. We were also grateful for the parking permits that allowed us to park nearby. The location was great—the neighbor was lovely, and we were happy to be so close to Lincoln Park. Overall, we’d recommend the space!
Guest favourite
Condo in Chicago
4.87 out of 5 average rating, 127 reviews

Newly updated 1BD/1B in Old Irving Chicago!

JoseRating, 5 stars1 month ago
The time spent here was wonderful. This place has everything you need to feel at home away from home. Everything was clean and comfortable. The area was also really nice with tons of food and drinks within walking distance. The blue line is a short walk away and the busses run on the corner. I would definitely stay here again when coming back to Chicago.
Guest favourite
Condo in Chicago
4.95 out of 5 average rating, 42 reviews

University of Chicago Condo-Upgraded and Spacious

Tatiana ARating, 5 stars1 week ago
13/10 stars ✨. Run do not WALK on this property for booking. I don’t even know where to start! i’ll try to keep it short! This property and Host has been the best i’ve ever experienced, Everrr!. Let’s start at the bathroom the tub is huge and deep- the perfect relaxation at your finger tips.. Spacious Home and beautifully decorated.. and Clean.. When you enter the home the fresh clean smells takes you over.. from the personalized birthday note to snacks to checking in to making sure everything was to my liking .. Chef’s kiss ❣️ Diane’s place is a piece of Heaven snuggled in the city of Chi-Town! Ladiessss if you need the perfect home to feel like a princess on every level book nowww.. This property has the best combo for a man or woman ! i can go on and on but just make sure when y’all book - you leave some dates open because i’m coming back here EVERY time❣️😘
Top Guest favourite
Condo in Chicago
5 out of 5 average rating, 29 reviews

Quick Drive to Downtown Chicago & Early Check-In

RoopaRating, 5 stars1 week 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.

Pet-friendly condo rentals

Superhost
Condo in Chicago
4.83 out of 5 average rating, 363 reviews

Chic and Charming Vintage Condominium in Lincoln Park

FojanRating, 5 stars3 days ago
We enjoyed our stay! First and foremost Colin was superb! Very responsive and respectful. Many pros about the place: loved the bright bedroom, walkable to many restaurants, neighborhood felt safe, we did not travel with young kids but kids bedroom could have been fun for young kids, the parking spot provided was a huge plus. cons were loud AC, mattress was not as comfortable as one would hope. Place could use some simple aesthetic up keep. Overall, we enjoyed our star and felt very comfortable! Thank you Colin for being above and beyond host :)
Top Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 180 reviews

RockStar Pad W3A BoysTown/Wrigley Field/Parking

StevenRating, 5 stars2 days ago
Will’s flat was exactly what my son and I needed on our trip to Chicago. It completely met our expectations and felt like home. My son was impressed with the comfort of the Murphy bed. The master bedroom was palatial and well-appointed. The kitchen had everything we needed, though we only used it for breakfast each day. As we were there primarily to take in a couple of baseball games we couldn’t have been happier with the location- Wrigley Field was only a few minutes away and we were close to the red line which took us to where the White Sox play. Will was very helpful with instructions and quick to respond to our questions. Absolutely would recommend this place without hesitation.
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 121 reviews

Luxuriously bright 3-bedroom condo: The Treehouse

MalloryRating, 5 stars5 days ago
Feven was very responsive to all our questions in real time. The place was perfect for four adults and two kids! The place was walkable to a few restaurants and coffee shops and easily drivable to other neighborhoods. We did happen to be in the neighborhood for the PR festival, which we didn’t realize. It made traffic a little tricky but otherwise we didn’t hear too much noise from the festivities. We found a nearby coffee shop and playground which we frequented daily and met lots of friendly neighbors on our walks.
Guest favourite
Condo in Chicago
4.94 out of 5 average rating, 127 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

BridgetteRating, 5 starstoday
The unit was as described, clean, affordable, easy to get to and home base from, and the neighborhood felt safe. There’s a coffee shop right on the corner we walked to in the mornings. We had a big group for a bachelorette and there was plenty of spaces to sleep downstairs (3 bedrooms with beds and one shared space with four beds), get ready (2 full bathrooms including two baths for kiddos), and lounge all together (large couch, big kitchen table, island seating, and outdoor covered area). Big thing for me is ceiling fans the bedrooms so that was super satisfying. Highly recommend this unit and we’d go back!
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 166 reviews

Ultra clean/cozy condo, 10 mins south of Downtown!

WilliamRating, 5 stars2 weeks ago
Crazy clean, super breezy place to stay. Neighborhood is fine, but not a lot of amenities. But it was a great place for us to be.
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 119 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars3 weeks ago
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!
Top Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 348 reviews

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

RachelRating, 5 stars2 days ago
Susan’s home was comfortable, clean, well-equipped, and aesthetically pleasing. The bed I slept in was one of the most comfortable of my entire life—I prefer a soft mattress. As far as location goes, the street was quiet, good for walking our dog, and close enough to public transport. Plenty of buses were available. We used street parking for our car and never had problems with finding a close spot to the house whenever we did take the car out. We enjoyed the stay greatly and will stay again. Thank you, Susan!
Superhost
Condo in Chicago
4.78 out of 5 average rating, 226 reviews

Modern Luxury In Old Town - Sleeps 4

MargaretRating, 5 stars6 days ago
We had a great stay. We love this area of Chicago so we were so pleased with the location. Robert is very responsive and was a great host!

Condo rentals with a pool

Guest favourite
Condo in Downers Grove
4.92 out of 5 average rating, 63 reviews

Upscale, Washer Dryer, Smoke Free, Pet Free,

ChidoRating, 5 stars3 months ago
I really loved the place—it was cozy, soundproof, and felt just like home. It had a warm, inviting atmosphere and a great sense of comfort. Plus, the neighborhood felt very safe, which made our stay even better.
Guest favourite
Condo in Evanston
4.96 out of 5 average rating, 97 reviews

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

PhillipRating, 5 stars1 month ago
Great Stay - Nice unit and facility. Michelle was very responsive and helpful during my stay. Would stay in one of her properties again when I’m back in town.
Superhost
Condo in Chicago
4.73 out of 5 average rating, 55 reviews

2BD Central Downtown Location! Spacious & Cozy

MadleneRating, 5 stars1 month ago
We were very happy with the Apartment, it was clean and perfect size for 4 people. Ana was super helpful and responded immediately, we loved talking to her 😄 For me due to Images, and wrong adress on the public profile, there has been some confusion about the location of the Apartment. All in all: The views are not stunning, but the location is perfect for sightseeing (and price was great location wise)! 😉
Condo in Chicago
4.45 out of 5 average rating, 11 reviews

voco: Balcony & City View

AmitRating, 5 stars2 weeks ago
gorgeous views and very nice condominium. great balcony and very safe. The elevators were super fast. Even though the actual location is different than the one mentioned in listing, it still wasn't disappointing. There is enough space for a small family or a couple.
Guest favourite
Condo in Evanston
4.95 out of 5 average rating, 108 reviews

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

StaciRating, 5 stars3 weeks ago
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.
Condo in Chicago
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 favourite
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 favourite
Condo in Evanston
4.91 out of 5 average rating, 126 reviews

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

FeiRating, 5 stars1 week ago
可以步行到西北大学,周边环境整洁舒适宜人。屋内设施齐全,很喜欢在厨房cooking。我们全家在这里度过了愉快的一周。下次还会入住。

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