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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Guest favourite
Flat in Chicago
Chic Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
8–13 Aug
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4.76 out of 5 average rating, 222 reviews
Top guest favourite
Flat in Chicago
Sun-filled top floor near 606 trail
4.77 out of 5 average rating, 569 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Room in Chicago
Lovely Front Room #1 in a New Renovated Apartment
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
4.9 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Flat in Chicago
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 Chicago
Loft with a baby grand and game room
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Top guest favourite
Guest suite in Chicago
Private entrance, walkable to the Blue Line
4.95 out of 5 average rating, 59 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
28 Nov – 3 Dec
Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
4.98 out of 5 average rating, 617 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Flat in Chicago
Eclectic vintage gem in Ukrainian Village
4.95 out of 5 average rating, 186 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
Top guest favourite
Home in Chicago
1908 coach house with rooftop skyline views
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 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
Guest favourite
Apartment in Chicago
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
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Guest favourite
Flat in Chicago
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
Top guest favourite
Flat in Forest Park
A treetop coach house near Oak Park
5.0 out of 5 average rating, 375 reviews, 1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Forest Park
Garden apartment 8 miles from downtown Chicago
4.98 out of 5 average rating, 187 reviews, 1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
Top guest favourite
Loft in Chicago
Vintage Chicago theme, walk to Wrigley
4.96 out of 5 average rating, 589 reviews, 1 bedroom, 2 beds, 1 bathroom
8–13 Nov