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Condo holiday rentals in South Side
Find and book unique condos on Airbnb
Top-rated condo rentals in South Side
Guests agree: These condos are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side condo rentals
Weekly condo rentals
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Condo in Chicago
4.86 out of 5 average rating, 107 reviewsTri-Taylor/Medical Dist. near West Loop
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Condo in Chicago
4.79 out of 5 average rating, 127 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
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Condo in Chicago
4.99 out of 5 average rating, 267 reviewsNorthside Chicago Favorite with parking!
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Condo in Chicago
4.99 out of 5 average rating, 587 reviewsUrban Comfort in the Heart of Chicago
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Condo in Chicago
4.91 out of 5 average rating, 316 reviewsSusie's Space. 2BR easy parking & pet friendly
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Condo in Chicago
4.96 out of 5 average rating, 113 reviewsLincoln Park 2bed/2bath in Historic Neighborhood
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Condo in Chicago
4.91 out of 5 average rating, 256 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
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Condo in Chicago
4.82 out of 5 average rating, 279 reviewsWelcoming 2BR in Chicago's Best Neighborhood!
Pet-friendly condo rentals
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Condo in Evanston
4.77 out of 5 average rating, 583 reviewsSpacious Evanston Unit - Walk to Northwestern U
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Condo in Chicago
4.99 out of 5 average rating, 206 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
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Condo in Chicago
4.99 out of 5 average rating, 104 reviewsRockStar Pad W3A BoysTown/Wrigley Field/Parking
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Condo in Chicago
4.83 out of 5 average rating, 321 reviewsChic and Charming Vintage Condominium in Lincoln Park
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Condo in Chicago
4.88 out of 5 average rating, 102 reviewsDowntown Mich Ave #7|Safe Park 2bd Penthouse|+gym
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Condo in Chicago
4.82 out of 5 average rating, 187 reviewsCan't Beat This 2min Walk to Wrigley!
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Condo in Chicago
4.78 out of 5 average rating, 204 reviewsModern Luxury In Old Town - Sleeps 4
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Condo in Chicago
4.95 out of 5 average rating, 135 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo rentals with a pool
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Condo in Chicago
4.74 out of 5 average rating, 156 reviewsCentral Downtown Location-Modern 2BR Condo
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Condo in Evanston
4.91 out of 5 average rating, 110 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
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Condo in Lisle
4.9 out of 5 average rating, 59 reviewsPeaceful Condo in Lisle, Illinois
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Condo in Chicago
4.74 out of 5 average rating, 23 reviewsLovely condo studio
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Condo in Lombard
4.95 out of 5 average rating, 39 reviewsPond View, Washer Dryer, Non Smoking, Pet Free
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Condo in Elk Grove Village
4.94 out of 5 average rating, 66 reviewsJust remodeled apartment close to airport and mall
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Condo in Chicago
4.72 out of 5 average rating, 32 reviews1 bedroom in the heart of downtown Chicago.
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Private room in Hillside
Lovely Guest Room W private bath rm.
Destinations to explore
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