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 Chinatown
4.82 out of 5 average rating, 159 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Dec 27 – Jan 3
Condo in Chicago
4.98 out of 5 average rating, 234 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Feb 23 – Mar 2
Condo in Chicago
4.99 out of 5 average rating, 565 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Chicago
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Jan 8 – 15
Condo in Chicago
4.95 out of 5 average rating, 131 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Chicago
4.81 out of 5 average rating, 445 reviewsCozy Apartment with Free On-Site Parking
Oct 23 – 30
Condo in Chicago
4.87 out of 5 average rating, 439 reviewsHumboldt Park Traveler's Lodge
Jun 21 – 28
Condo in Chicago
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
Dec 13 – 20
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Jan 13 – 20
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
4.83 out of 5 average rating, 178 reviewsCan't Beat This 2min Walk to Wrigley!
Feb 7 – 14
Condo in Chicago
4.82 out of 5 average rating, 117 reviewsCharming Condo near U.C./Loop/McCormick Place
Sep 29 – Oct 6
Condo in Chicago
4.78 out of 5 average rating, 201 reviewsModern Luxury In Old Town - Sleeps 4
Apr 19 – 26
Condo in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
Dec 16 – 23
Condo in The Loop
4.8 out of 5 average rating, 169 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Jun 16 – 23
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Nov 18 – 25
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 7 – 14
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
Mar 23 – 30
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Oct 25 – Nov 1
Condo in Lombard
4.97 out of 5 average rating, 36 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
Nov 24 – Dec 1
Condo in Chicago
4.75 out of 5 average rating, 16 reviewsLovely condo studio
Dec 14 – 21
Condo in Chicago
4.7 out of 5 average rating, 27 reviews1 bedroom in the heart of downtown Chicago.
Jul 9 – 16
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Dec 30 – Jan 6
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