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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.98 out of 5 average rating, 253 reviews
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Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed
22–27 Nov
4.97 out of 5 average rating, 921 reviews
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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 39 reviews
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Top guest favourite
Flat in Uptown
Private studio near Wrigley
1 bedroom, 2 beds
29 Nov – 4 Dec
4.93 out of 5 average rating, 153 reviews
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Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 111 reviews
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Guest favourite
Flat in Lake View
Furnished Lakeview Studio Near Wrigley Field
1 queen bed
24–29 Oct
5.0 out of 5 average rating, 5 reviews
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Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
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Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 959 reviews
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Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed
4–9 Jan
4.96 out of 5 average rating, 325 reviews
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Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
21–26 Oct
5.0 out of 5 average rating, 58 reviews
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Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed
6–11 Sept
New place to stay
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Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
6–11 Sept
4.88 out of 5 average rating, 146 reviews
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Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
23–28 Oct
4.92 out of 5 average rating, 74 reviews
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Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
16–21 Nov
4.95 out of 5 average rating, 171 reviews
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Top guest favourite
Apartment in Lincoln Park
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 reviews
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Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 28 reviews