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, 563 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Chicago
4.98 out of 5 average rating, 233 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Sep 12 – 19
Condo in Chicago
5.0 out of 5 average rating, 100 reviewsSpacious 4 Bedroom Condo
Apr 6 – 13
Condo in Chicago
4.86 out of 5 average rating, 437 reviewsHumboldt Park Traveler's Lodge
Jun 20 – 27
Condo in Chicago
4.91 out of 5 average rating, 247 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Jan 15 – 22
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, 444 reviewsCozy Apartment with Free On-Site Parking
Sep 5 – 12
Condo in Chicago
4.82 out of 5 average rating, 125 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Jun 15 – 22
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 567 reviewsSpacious Evanston Unit - Walk to Northwestern U
Jan 2 – 9
Condo in Chicago
4.99 out of 5 average rating, 182 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Nov 1 – 8
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
4.78 out of 5 average rating, 200 reviewsModern Luxury In Old Town - Sleeps 4
Oct 20 – 27
Condo in Portage
4.8 out of 5 average rating, 158 reviewsMarina Condo near Lake Michigan
Apr 16 – 23
Condo in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
Jul 14 – 21
Condo in The Loop
4.77 out of 5 average rating, 160 reviewsSafe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Jun 27 – Jul 4
Condo in Chicago
4.91 out of 5 average rating, 297 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 13 – 20
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 146 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 10 – 17
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
Apr 3 – 10
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Nov 16 – 23
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Aug 16 – 23
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Sep 16 – 23
Condo in Portage
4.94 out of 5 average rating, 68 reviewsUnsalted Stay - Waterfront Condo
Jul 11 – 18
Condo in Portage
4.91 out of 5 average rating, 23 reviewsSerenity on the Shores
Mar 18 – 25
Destinations to explore
- Downtown Chicago Vacation rentals
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