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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Flat in Chicago
Modern vintage chic steps from Wrigley: park free
3 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.96 out of 5 average rating, 271 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 121 reviews
Guest favourite
Home in Chicago
Patio with swing chairs near United Center
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.9 out of 5 average rating, 60 reviews
Top guest favourite
Flat in Chicago
Historic 1884 row house across from park
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Chicago
Loft with a baby grand and game room
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chicago
1888 cottage with an 85-inch TV
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Home in Chicago
1908 coach house with rooftop skyline views
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 236 reviews
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Chicago
Vintage Ukrainian Village Apartment
2 bedrooms, 2 double beds, 1 bathroom
14–19 Nov
4.95 out of 5 average rating, 186 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Chicago
Great place in the Heart of Pilsen
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
4.96 out of 5 average rating, 23 reviews
Guest favourite
Room in Chicago
Tree-lined street, 3 blocks from Blue Line
2 single beds, 1 bathroom
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Top guest favourite
Flat in Chicago
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.77 out of 5 average rating, 569 reviews
Top guest favourite
Flat in Forest Park
Like a Treehouse!
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 375 reviews