Vacation rentals in South Side
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Top-rated vacation rentals in South Side
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side vacation rentals
Other great vacation rentals in South Side
Guest favorite
Guesthouse in Kenwood
4.88 out of 5 average rating, 17 reviewsLuxe Loft studio - Great location!
Jul 3 – 10
R2,137 ZAR per night
Guest favorite
Vacation home in South Shore
4.95 out of 5 average rating, 41 reviewsUChicago Luxurious King Suite Lakefront
Nov 10 – 17
R2,117 ZAR per night
Guest favorite
Guest suite in Chicago
4.93 out of 5 average rating, 40 reviewsClassic Den @ U Chicago
Aug 23 – 30
R2,087 ZAR per night
Guest favorite
Apartment in Woodlawn
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Oct 1 – 8
R1,788 ZAR per night
Guest favorite
Apartment in Chicago
5.0 out of 5 average rating, 22 reviewsTravel To Chicago New City
Feb 6 – 13
R1,866 ZAR per night
Guest favorite
Apartment in Chicago
4.97 out of 5 average rating, 60 reviewsLocation! Location! Location!
Jul 13 – 20
R2,635 ZAR per night
Superhost
Apartment in Chicago
4.9 out of 5 average rating, 62 reviewsEclipse: Apt. in Woodlawn | Near UChicago
Jan 20 – 27
R2,258 ZAR per night
Superhost
Guest suite in Bronzeville
4.85 out of 5 average rating, 95 reviewsBronzeville Guest Suite - 1 Br
Oct 5 – 12
R1,835 ZAR per night
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- Rentals with lake access South Side
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