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 Chicago
4.91 out of 5 average rating, 111 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Sep 25 – Oct 2
Apartment in Chicago
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 5 – 12
Apartment in Blue Island
4.93 out of 5 average rating, 265 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Dec 24 – 31
Apartment in Chicago
4.85 out of 5 average rating, 273 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Nov 18 – 25
Apartment in Chicago
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apr 21 – 28
Apartment in Chicago
4.81 out of 5 average rating, 145 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Oct 6 – 13
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Sep 23 – 30
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Private apartment rentals
Apartment in Chicago
5.0 out of 5 average rating, 20 reviewsUrban Cottage
Oct 17 – 24
Apartment in Chicago
5.0 out of 5 average rating, 25 reviewsTravel To Chicago New City
Mar 8 – 15
Apartment in Chicago
4.97 out of 5 average rating, 61 reviewsLocation! Location! Location!
Jul 27 – Aug 3
Apartment in Chicago
4.94 out of 5 average rating, 66 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Jul 4 – 11
Apartment in Chicago
4.8 out of 5 average rating, 15 reviewsTaste the Best of Chicago
Jan 12 – 19
Apartment in Chicago
4.92 out of 5 average rating, 53 reviewsStunning Basement Apartment w/free street parking!
Apr 16 – 23
Apartment in East Side
4.97 out of 5 average rating, 37 reviewsVela Loft w/2 BR & Modern Design
Jan 10 – 17
Apartment in Bridgeport
4.89 out of 5 average rating, 35 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Mar 30 – Apr 6
Apartment rentals with a hot tub
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Oct 3 – 10
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 24 – 31
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov 25 – Dec 2
Apartment in The Loop
5.0 out of 5 average rating, 7 reviewsThe Downtown Oasis (2BD / 2BA)
Feb 10 – 17
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Jun 29 – Jul 6
Apartment in West Rogers Park
4.9 out of 5 average rating, 20 reviewsSpacious Beautiful Condo
Oct 23 – 30
Apartment in Chicago
5.0 out of 5 average rating, 26 reviewsBelmont Pleasures - hot tub / arcade gaming room
Feb 17 – 24
Apartment in Chicago
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
Feb 24 – Mar 3
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