Condo vacation rentals in Chicago
Find and book unique condos on Airbnb
Top-rated condo rentals in Chicago
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago condo rentals
Weekly condo rentals
Condo in Chicago
4.92 out of 5 average rating, 293 reviewsBright 2br Apt W/ Private Entrance & Laundry
Feb 5 – 12
Condo in Wrigleyville
4.97 out of 5 average rating, 119 reviewsWrigleyville Inn. Historic Greystone. Parking pass
Jan 6 – 13
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
Oct 17 – 24
Condo in Chicago
4.87 out of 5 average rating, 117 reviewsQuiet, Modern, Convenient 2 bedroom condo
Oct 15 – 22
Condo in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
Sep 27 – Oct 4
Condo in Oak Park
4.79 out of 5 average rating, 308 reviewsPeaceful Oak Park Condo Next to Green Line Metro
Oct 13 – 20
Condo in Chicago
4.96 out of 5 average rating, 112 reviewsBest Lincoln Square location. Spacious 2 bedroom
Jan 11 – 18
Condo in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Nov 17 – 24
Condo in Chicago
4.83 out of 5 average rating, 307 reviewsChic and Charming Vintage Condominium in Lincoln Park
Jan 29 – Feb 5
Condo in Chicago
4.91 out of 5 average rating, 296 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 19 – 26
Condo in Chicago
4.99 out of 5 average rating, 212 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar 16 – 23
Condo in Chicago
4.82 out of 5 average rating, 177 reviewsCan't Beat This 2min Walk to Wrigley!
Nov 21 – 28
Condo in Chicago
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
Nov 18 – 25
Condo in Chicago
4.95 out of 5 average rating, 128 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Jan 11 – 18
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 3 – 10
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Dec 9 – 16
Condo in Lisle
4.95 out of 5 average rating, 41 reviewsPeaceful Condo in Lisle, Illinois
Mar 12 – 19
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov 21 – 28
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Sep 27 – Oct 4
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Jan 29 – Feb 5
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 7 – 14
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Jan 6 – 13
Quick stats about condo rentals in Chicago
Total rentals
1.1K properties
Rentals with dedicated workspaces
630 properties have a dedicated workspace
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
300 properties allow pets
Family-friendly rentals
640 properties are a good fit for families
Total number of reviews
61K reviews
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Rentals with breakfast Chicago
- Rentals with pools Chicago
- Rentals with a balcony Chicago
- Rentals with an accessible height bed Chicago
- Monthly Rentals Chicago
- Rentals with lake access Chicago
- Beachfront rentals Chicago
- Rentals with beach access Chicago
- Rentals with a washer and dryer Chicago
- Townhouse rentals Chicago
- Rentals with a sauna Chicago
- Waterfront rentals Chicago
- Family-friendly rentals Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Rentals with a home theater Chicago
- Villa rentals Chicago
- Rentals with a fire pit Chicago
- Rentals with outdoor seating Chicago
- Fitness-friendly rentals Chicago
- House rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with an EV charger Chicago
- Rentals with a hot tub Chicago
- Hotel rentals Chicago
- Apartment rentals Chicago
- Lakehouse rentals Chicago
- Pet-friendly rentals Chicago
- Guesthouse rentals Chicago
- Private suite rentals Chicago
- Smoking-friendly rentals Chicago
- Mansion rentals Chicago
- Rentals with a fireplace Chicago
- Cottage rentals Chicago
- Condo rentals Downtown Chicago
- Condo rentals Milwaukee
- Condo rentals Chicago Loop
- Condo rentals Illinois
- Condo rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom