Apartment vacation rentals in South Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for South Side apartment rentals
Weekly apartment rentals
Apartment in Blue Island
4.93 out of 5 average rating, 266 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Apartment in Oak Park
4.85 out of 5 average rating, 534 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Chicago
4.91 out of 5 average rating, 112 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Apartment in Chicago
4.9 out of 5 average rating, 260 reviewsBright & Lofty Bucktown 1br
Apartment in Chicago
4.82 out of 5 average rating, 146 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Apartment in Chicago
4.83 out of 5 average rating, 162 reviewsChicago Vintage Home
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Forest Park
4.84 out of 5 average rating, 118 reviewsHome away from home downstairs
Private apartment rentals
Apartment in Chicago
4.99 out of 5 average rating, 145 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Apartment in Chicago
5.0 out of 5 average rating, 28 reviewsTravel To Chicago New City
Apartment in Chicago
4.97 out of 5 average rating, 64 reviewsLocation! Location! Location!
Apartment in Chicago
4.9 out of 5 average rating, 69 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Chicago
4.89 out of 5 average rating, 36 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Apartment in Chicago
5.0 out of 5 average rating, 24 reviewsUrban Cottage
Apartment in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
Apartment rentals with a hot tub
Apartment in Berwyn
4.91 out of 5 average rating, 205 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Apartment in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in Chicago
4.82 out of 5 average rating, 22 reviewsSpacious Beautiful Condo
Destinations to explore
- Downtown Chicago Vacation rentals
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- House rentals South Side
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- Condo rentals South Side
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- Rentals with outdoor seating South Side
- Monthly Rentals South Side
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