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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Flat in Edgewater
Andersonville Garden Living
1 bedroom, 3 beds, 1 private bathroom
5–10 Sept
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4.83 out of 5 average rating, 149 reviews
Guest favourite
Flat in West Side
Eclectic decor in Pilsen’s art district
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
4.9 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Little Italy
Historic 1884 row house across from park
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Flat in Bridgeport
1888 cottage with an 85-inch TV
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 236 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Portage Park
Free parking and a home gym
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Flat in Ukrainian Village
Eclectic vintage gem in Ukrainian Village
4.95 out of 5 average rating, 186 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in West Side
Soaring ceilings and skylights in Pilsen
5.0 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 569 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Flat in Downtown Chicago
Designer loft with views in Gold Coast
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Room in Irving Park
Tree-lined street, 3 blocks from Blue Line
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Top guest favourite
Flat in West Side
Private patio steps from Thalia Hall
4.96 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug