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 Chicago
4.98 out of 5 average rating, 297 reviewsRedesigned Lower Level Studio in Historic Building
Oct 16 – 23
Apartment in Chicago
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Mar 30 – Apr 6
Apartment in Humboldt Park
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
Oct 15 – 22
Apartment in Chicago
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 10 – 17
Apartment in Chicago
4.85 out of 5 average rating, 273 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Nov 19 – 26
Apartment in Blue Island
4.93 out of 5 average rating, 264 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Sep 6 – 13
Apartment in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
Oct 13 – 20
Apartment in Oak Park
4.85 out of 5 average rating, 529 reviewsLong stays welcome@warm&cute vintage 2BR
Oct 3 – 10
Private apartment rentals
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Jan 2 – 9
Apartment in Avondale
4.97 out of 5 average rating, 117 reviewsDesigner Avondale Attic
Jul 6 – 13
Apartment in Chicago
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Nov 13 – 20
Apartment in Chicago
5.0 out of 5 average rating, 24 reviewsTravel To Chicago New City
Nov 5 – 12
Apartment in Chicago
4.97 out of 5 average rating, 61 reviewsLocation! Location! Location!
Jul 22 – 29
Apartment in Chicago
4.9 out of 5 average rating, 62 reviewsEclipse: Apt. in Woodlawn | Near UChicago
Jan 31 – Feb 7
Apartment in Chicago
4.8 out of 5 average rating, 15 reviewsTaste the Best of Chicago
Oct 30 – Nov 6
Apartment in Chicago
5.0 out of 5 average rating, 19 reviewsUrban Cottage
Sep 16 – 23
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Jan 1 – 8
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Aug 27 – Sep 3
Apartment in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
Apr 26 – May 3
Apartment in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Dec 21 – 28
Apartment in Chicago
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Jan 11 – 18
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Aug 29 – Sep 5
Apartment in Chicago
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 9 – 16
Apartment in Chicago
4.78 out of 5 average rating, 9 reviewsThe Areal Oasis
Jul 3 – 10
Destinations to explore
- Downtown Chicago Vacation rentals
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