Condo vacation rentals in Chicago
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Top-rated condo rentals in Chicago
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chicago condo rentals
Weekly condo rentals
Condo in Chicago
4.95 out of 5 average rating, 131 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Chicago
4.87 out of 5 average rating, 117 reviewsQuiet, Modern, Convenient 2 bedroom condo
Oct. 14 – 21
Condo in Chicago
4.83 out of 5 average rating, 308 reviewsChic and Charming Vintage Condominium in Lincoln Park
Dec. 5 – 12
Condo in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
Sep. 27 – Oct. 4
Condo in Chicago
4.9 out of 5 average rating, 191 reviewsA Stones Throw from U Chicago South Campus!
Aug. 20 – 27
Condo in Chicago
4.96 out of 5 average rating, 126 reviewsEast Lakeview Designer Condo with 2 Bd, 2 Bath
Jan. 17 – 24
Condo in Little Italy
4.96 out of 5 average rating, 119 reviewsPrivate hot tub - King bed suite - Free parking
Jul. 19 – 26
Condo in Oak Park
4.98 out of 5 average rating, 126 reviewsPicture Perfect 3Bed Steps from Train and FLW
Feb. 20 – 27
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
Jan. 5 – 12
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Sep. 17 – 24
Condo in Chicago
4.91 out of 5 average rating, 297 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul. 19 – 26
Condo in Chicago
4.99 out of 5 average rating, 213 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar. 16 – 23
Condo in Chicago
4.83 out of 5 average rating, 178 reviewsCan't Beat This 2min Walk to Wrigley!
Mar. 3 – 10
Condo in Lincoln Park
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
Oct. 20 – 27
Condo in Chicago
4.82 out of 5 average rating, 117 reviewsCharming Condo near U.C./Loop/McCormick Place
Dec. 12 – 19
Condo in Chicago
4.79 out of 5 average rating, 107 reviewsSpacious Home, Incredible Lakeview Location
Oct. 30 – Nov. 6
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 145 reviewsCentral Downtown Location-Modern 2BR Condo
Jul. 21 – 28
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Dec. 2 – 9
Condo in Lisle
4.95 out of 5 average rating, 42 reviewsPeaceful Condo in Lisle, Illinois
Jan. 28 – Feb. 4
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Oct. 26 – Nov. 2
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Jan. 10 – 17
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Nov. 3 – 10
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul. 21 – 28
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Dec. 11 – 18
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
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