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
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Popular amenities for South Side vacation rentals
Other great vacation rentals in South Side
Superhost
Guest suite in Chicago
4.91 out of 5 average rating, 169 reviewsChicago Living: Your Home Away From Home
Dec. 15 – 22
$263 CAD per night
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 40 reviewsClassic Den @ U Chicago
Aug. 24 – 31
$194 CAD per night
Superhost
Home in Washington Park
4.8 out of 5 average rating, 15 reviewsCozy 2 bed Condo in Bronzeville!
Aug. 22 – 29
$208 CAD per night
Guest favourite
Home in Mount Greenwood
4.91 out of 5 average rating, 88 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Dec. 5 – 12
$208 CAD per night
Guest favourite
Vacation home in Chicago
4.95 out of 5 average rating, 42 reviewsUChicago Luxurious King Suite Lakefront
Nov. 10 – 17
$234 CAD per night
Guest favourite
Apartment in Woodlawn
5.0 out of 5 average rating, 6 reviewsRenovated Retreat near U of Chicago
Dec. 28 – Jan. 4
$169 CAD per night
Guest favourite
Apartment in Chicago
4.94 out of 5 average rating, 66 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Jul. 4 – 11
$265 CAD per night
Guest favourite
Apartment in Bridgeport
5.0 out of 5 average rating, 20 reviewsUrban Cottage
Oct. 17 – 24
$229 CAD per night
Destinations to explore
- Downtown Chicago Vacation rentals
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- Rentals with breakfast South Side
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