Apartment vacation rentals in South Side
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Top-rated apartment rentals in South Side
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for South Side apartment rentals
Weekly apartment rentals
Apartment in Oak Park
4.86 out of 5 average rating, 234 reviewsCozy and Character-Rich Chicago Style, Tv NFL PASS
Apartment in Oak Park
4.86 out of 5 average rating, 540 reviewsLong stays welcome@warm&cute vintage 2BR
Apartment in Berwyn
4.87 out of 5 average rating, 151 reviewsThe Green Bungalow: Charming 1-BR apt. with patio
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.91 out of 5 average rating, 116 reviewsModern 2BRD apartment| 5min to McCormick Place
Apartment in Chicago
4.82 out of 5 average rating, 137 reviewsPerfect Private Getaway in Perfect Pilsen
Apartment in Chicago
4.82 out of 5 average rating, 443 reviewsLovely Andersonville Apt with Ideal Location
Apartment in Chicago
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Private apartment rentals
Apartment in Chicago
4.97 out of 5 average rating, 124 reviewsDesigner Avondale Attic
Apartment in Chicago
4.94 out of 5 average rating, 271 reviewsLovely City Apartment-Near Downtown-Food-Train
Apartment in Chicago
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Chicago
4.99 out of 5 average rating, 149 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in Chicago
5.0 out of 5 average rating, 17 reviewsHistoric Charm Near Shops &Parks and UChicago
Apartment in Chicago
4.94 out of 5 average rating, 32 reviewsTravel To Chicago New City
Apartment in Chicago
4.91 out of 5 average rating, 74 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Chicago
4.89 out of 5 average rating, 37 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Apartment rentals with a hot tub
Apartment in Chicago
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.87 out of 5 average rating, 108 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in Chicago
4.83 out of 5 average rating, 30 reviewsThe Professional's Playground
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, 12 reviewsSkyline Oasis: City & Lake Views
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- Family travel hub Tips and inspiration
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