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
4.83 out of 5 average rating, 160 reviewsChicago Vintage Home
Dec 9 – 16
Apartment in Chicago
4.91 out of 5 average rating, 110 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Dec 30 – Jan 6
Apartment in Chicago
4.85 out of 5 average rating, 273 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Oct 21 – 28
Apartment in Chicago
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Dec 10 – 17
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 13 – 20
Apartment in Near North Side
4.89 out of 5 average rating, 370 reviewsGreat Location Studio in the Gold Coast!!
Jan 22 – 29
Apartment in Chicago
4.91 out of 5 average rating, 169 reviewsHandicap accessible apartment w/Level-2 EV Charger
Aug 18 – 25
Apartment in Chicago
4.81 out of 5 average rating, 143 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Jul 17 – 24
Private apartment rentals
Apartment in Uptown
4.96 out of 5 average rating, 265 reviewsCozy loft in Chicago's Uptown
Oct 14 – 21
Apartment in Blue Island
4.93 out of 5 average rating, 264 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Oct 26 – Nov 2
Apartment in Chicago
4.99 out of 5 average rating, 103 reviewsNewly Renovated, Spacious 2BR in Andersonville
Jan 28 – Feb 4
Apartment in Forest Park
5.0 out of 5 average rating, 219 reviewsLike a Treehouse!
Sep 5 – 12
Apartment in Chicago
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Sep 9 – 16
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsModern 1BR Chicago Hideaway
May 1 – 8
Apartment in Chicago
4.9 out of 5 average rating, 62 reviewsEclipse: Apt. in Woodlawn | Near UChicago
Jan 27 – Feb 3
Apartment in Chicago
4.97 out of 5 average rating, 60 reviewsLocation! Location! Location!
Jul 3 – 10
Apartment rentals with a hot tub
Apartment in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 2 – 9
Apartment in Berwyn
4.91 out of 5 average rating, 201 reviews“Dream slice of urban homesteading.”
Feb 9 – 16
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Jul 16 – 23
Apartment in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
May 15 – 22
Apartment in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 10 – 17
Apartment in Chicago
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
May 6 – 13
Apartment in Chicago
4.86 out of 5 average rating, 44 reviewsSpectacular Rooftop Getaway in Heart of City
Aug 29 – Sep 5
Apartment in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
Sep 10 – 17
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- Family travel hub Tips and inspiration
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