Condo vacation rentals in South Side
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Top-rated condo rentals in South Side
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for South Side condo rentals
Weekly condo rentals
Condo in Chicago
4.99 out of 5 average rating, 561 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Chinatown
4.82 out of 5 average rating, 159 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
May 6 – 13
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Apr 29 – May 6
Condo in Chicago
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
Feb 17 – 24
Condo in Chicago
4.81 out of 5 average rating, 265 reviewsWelcoming 2BR in Chicago's Best Neighborhood!
Jun 12 – 19
Condo in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Oak Park
4.98 out of 5 average rating, 126 reviewsPicture Perfect 3Bed Steps from Train and FLW
Feb 20 – 27
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
Sep 5 – 12
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
4.99 out of 5 average rating, 213 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar 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
4.91 out of 5 average rating, 297 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 19 – 26
Condo in Chicago
4.82 out of 5 average rating, 117 reviewsCharming Condo near U.C./Loop/McCormick Place
Dec 17 – 24
Condo in Chicago
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
Oct 20 – 27
Condo in The Loop
4.77 out of 5 average rating, 160 reviewsSafe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Jun 9 – 16
Condo in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
Jul 14 – 21
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
Destinations to explore
- Downtown Chicago Vacation rentals
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