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
Condo rentals with a hot tub
Condo in Wicker Park
4.94 out of 5 average rating, 32 reviewsLuxury Duplex w/ HOT TUB and Amazing Roof Top Deck
Condo in Lincoln Square
4.92 out of 5 average rating, 99 reviewsThe Fox Den
Condo in Wicker Park
4.93 out of 5 average rating, 29 reviewsLuxury Duplex w/ HOT TUB and Amazing Roof Deck!
Condo in West Town
4.96 out of 5 average rating, 104 reviewsDowntown Chicago - Spa Bath, Patio, 3 blocks to L
Condo in Near West Side
4.96 out of 5 average rating, 47 reviewsModern Gem Near United Center with Free Parking
Condo in Skokie
4.92 out of 5 average rating, 74 reviewsFree Parking, Balcony, Weekly 5% Monthly 10% Off
Condo in Lincoln Square
5 out of 5 average rating, 6 reviewsLincoln Square Retreat
Condo in Chicago
4.97 out of 5 average rating, 31 reviewsStylish & Cozy 2 Bedroom Near the United Center
Weekly condo rentals
Condo in Lincoln Park
4.84 out of 5 average rating, 340 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Lincoln Park
4.99 out of 5 average rating, 248 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Condo in Woodlawn
4.9 out of 5 average rating, 220 reviewsA Stones Throw from U Chicago South Campus!
Condo in Palos Hills
4.84 out of 5 average rating, 176 reviews~Home Comforts, Roku SmartTV, Fast WiFi~
Condo in West Town
4.97 out of 5 average rating, 154 reviewsSunny Tri Level
Condo in Chicago
4.92 out of 5 average rating, 134 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Lake View
4.98 out of 5 average rating, 104 reviews💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
Condo in Uptown
4.98 out of 5 average rating, 244 reviewsNear Lake Michigan & Wrigley Field
Pet-friendly condo rentals
Condo in Pilsen Historic District
4.86 out of 5 average rating, 118 reviews816 PLZ-N Lux Apt | Rooftop | Garage Parking
Condo in Bridgeport
4.95 out of 5 average rating, 118 reviewsEntire 3Bed/2Bath Condo Near McCormick & Metro
Condo in Bridgeport
4.89 out of 5 average rating, 102 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Condo in Lake View
4.81 out of 5 average rating, 124 reviewsSpacious Home, Incredible Lakeview Location
Condo in West Town
4.95 out of 5 average rating, 40 reviewsTwo Bedroom w Porch in Wicker Park
Condo in Lincoln Park
4.79 out of 5 average rating, 209 reviewsModern Luxury In Old Town - Sleeps 4
Condo in Woodlawn
4.97 out of 5 average rating, 33 reviewsModern Apt Near U of Chicago!
Condo in Evanston
4.77 out of 5 average rating, 608 reviewsSpacious Evanston Unit - Walk to Northwestern U
Quick stats about condo rentals in Chicago
Total rentals
1.1K properties
Total number of reviews
65K reviews
Family-friendly rentals
640 properties are a good fit for families
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
90 properties have a pool
Rentals with dedicated workspaces
640 properties have a dedicated workspace
Destinations to explore
- Downtown Chicago Vacation rentals
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