Condo vacation rentals in Chicago
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Top-rated condo rentals in Chicago
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Vacation rentals for every style
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Popular amenities for Chicago condo rentals
Weekly condo rentals
Condo in Chicago
4.86 out of 5 average rating, 437 reviewsHumboldt Park Traveler's Lodge
Jun 20 – 27
Condo in Chicago
4.98 out of 5 average rating, 201 reviewsNear Lake Michigan & Wrigley Field
Sep 26 – Oct 3
Condo in Chicago
4.82 out of 5 average rating, 125 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Jun 15 – 22
Condo in East Garfield Park
4.9 out of 5 average rating, 136 reviewsEast Garfield Park 2 Bedroom
Nov 16 – 23
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
4.92 out of 5 average rating, 294 reviewsBright 2br Apt W/ Private Entrance & Laundry
Feb 11 – 18
Condo in Chicago
4.98 out of 5 average rating, 283 reviewsSunny Apartment Just 2 Blocks from Wrigley and Boystown
Aug 12 – 19
Condo in Chicago
4.92 out of 5 average rating, 113 reviewsStunning, Spacious, & Sun-Soaked 1br Uptown Condo
Oct 14 – 21
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
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 19 – 26
Condo in Chicago
4.83 out of 5 average rating, 178 reviewsCan't Beat This 2min Walk to Wrigley!
Nov 26 – Dec 3
Condo in Chicago
4.83 out of 5 average rating, 308 reviewsChic and Charming Vintage Condominium in Lincoln Park
Mar 4 – 11
Condo in Chicago
4.92 out of 5 average rating, 100 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Dec 12 – 19
Condo in Chicago
4.78 out of 5 average rating, 200 reviewsModern Luxury In Old Town - Sleeps 4
Dec 11 – 18
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, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 4 – 11
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
Mar 25 – Apr 1
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov 23 – 30
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Dec 31 – Jan 7
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Oct 15 – 22
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 27 – Jan 3
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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