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
Get the amount of space that is right for you
Popular amenities for Chicago condo rentals
Weekly condo rentals
Condo in Little Italy
4.96 out of 5 average rating, 120 reviewsPrivate hot tub - King bed suite - Free parking
Jul 27 – Aug 3
Condo in Chicago
4.81 out of 5 average rating, 445 reviewsCozy Apartment with Free On-Site Parking
Oct 26 – Nov 2
Condo in Chicago
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Apr 21 – 28
Condo in Chicago
4.91 out of 5 average rating, 121 reviewsSpacious & Modern Family Friendly North Center Apt
Mar 8 – 15
Condo in Chicago
4.98 out of 5 average rating, 203 reviewsNear Lake Michigan & Wrigley Field
Sep 27 – Oct 4
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Oct 29 – Nov 5
Condo in Chicago
4.92 out of 5 average rating, 248 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Apr 1 – 8
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Nov 19 – 26
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Feb 9 – 16
Condo in Chicago
4.99 out of 5 average rating, 214 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar 16 – 23
Condo in Chicago
4.91 out of 5 average rating, 298 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 8 – 15
Condo in Chicago
4.83 out of 5 average rating, 308 reviewsChic and Charming Vintage Condominium in Lincoln Park
Apr 19 – 26
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, 201 reviewsModern Luxury In Old Town - Sleeps 4
Feb 28 – Mar 7
Condo in Chicago
4.92 out of 5 average rating, 100 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Oct 30 – Nov 6
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
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 11 – 18
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Aug 12 – 19
Condo in Lisle
4.95 out of 5 average rating, 43 reviewsPeaceful Condo in Lisle, Illinois
Oct 11 – 18
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Dec 7 – 14
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Dec 7 – 14
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Dec 12 – 19
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 26 – Aug 2
Room in Hillside
Lovely Guest Room W private bath rm.
Jul 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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