Chicago, IL, USA Vacation Rentals

Discover popular destinations in and around Chicago

Chicago Loop
107 vacation rentals
Magnificent Mile
4 vacation rentals
Lincoln Park
72 vacation rentals
River North
56 vacation rentals
Gold Coast
10 vacation rentals
Wrigleyville
82 vacation rentals
Chicago Water Tower
700 vacation rentals
Wicker Park
24 vacation rentals
Lakeview
74 vacation rentals
South Loop
19 vacation rentals
Bucktown
19 vacation rentals
West Loop
9 vacation rentals
Downtown Chicago
700 vacation rentals
Hyde Park
4 vacation rentals
Near North Side
121 vacation rentals
Old Town
52 vacation rentals
Logan Square
12 vacation rentals
Loop
104 vacation rentals

Explore a selection of Chicago vacation rentals