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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Guest house in Wicker Park
Coach House with Garage Parking & EV Charging
1 bedroom, 1 bed, 1 private bathroom
15–20 Nov
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4.98 out of 5 average rating, 103 reviews
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Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
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, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Top guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
8–13 Nov
4.96 out of 5 average rating, 601 reviews
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Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
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, 1 bathroom
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, 3 bathrooms
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, 1 bathroom
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, 1 bathroom
20–25 Sept
New place to stay
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Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
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, 1 bathroom
6–11 Sept
4.88 out of 5 average rating, 146 reviews
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Top guest favourite
Room in Lake View
En Suite Private Queen Bedroom/Bathroom
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 273 reviews
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Featured hotel
Room in Downtown Chicago
Studio suite
1 bathroom
6–11 Sept
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Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
23–28 Oct
4.92 out of 5 average rating, 74 reviews
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Top guest favourite
Flat in Chicago Loop
Spacious 1-bedroom South Loop Loft I Sleep 5
1 bedroom, 4 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 247 reviews
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Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed, 1 bathroom
4–9 Jan
4.96 out of 5 average rating, 325 reviews
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Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
6–11 Sept
New place to stay
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 58 reviews