South Side, Chicago, IL, USA Vacation Rentals

Discover popular destinations in and around South Side

Lake Michigan
9,508 vacation rentals
Chicago Loop
105 vacation rentals
Downtown Chicago
813 vacation rentals
Indiana Dunes National Lakeshore
315 vacation rentals
Lincoln Park
835 vacation rentals
River North
55 vacation rentals
Wrigleyville
97 vacation rentals
Magnificent Mile
811 vacation rentals
Evanston
635 vacation rentals
Indiana
1,112 vacation rentals
Hyde Park
544 vacation rentals
Grant Park
865 vacation rentals
Logan Square
834 vacation rentals
Lakeview
94 vacation rentals
Wicker Park
28 vacation rentals
Chicago Water Tower
867 vacation rentals
Oak Park
823 vacation rentals
Old Town
50 vacation rentals
Gary
51 vacation rentals
South Loop
30 vacation rentals

Explore a selection of South Side vacation rentals