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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Wrigleyville
Taj Ma-small • Vintage 1BR Near Wrigley
1 bedroom, 1 bed, 1 shared bathroom
26–31 Oct
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4.91 out of 5 average rating, 280 reviews
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Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 111 reviews
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Top guest favourite
Flat in West Town
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed, 1 bathroom
6–11 Dec
4.97 out of 5 average rating, 635 reviews
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Guest favourite
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 6 reviews
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Flat in West Side
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in West Rogers Park
Cozy Chicago Studio | Washer, Near Transit & Eat
1 queen bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Guest suite in Andersonville
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.96 out of 5 average rating, 417 reviews
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Top guest favourite
Guest suite in Portage Park
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 178 reviews
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Top guest favourite
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Guest house in Edgewater
Cozy Coach House
1 queen bed, 1 bathroom
25–30 Oct
4.96 out of 5 average rating, 515 reviews
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Top guest favourite
Apartment in Wicker Park
Two Bedroom w Porch in Wicker Park
2 bedrooms, 2 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 123 reviews
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Top guest favourite
Flat in Uptown
Private studio near Wrigley
1 bedroom, 2 beds, 1 bathroom
2–7 Jan
4.93 out of 5 average rating, 161 reviews
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Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.95 out of 5 average rating, 76 reviews
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Guest favourite
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
2–7 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Flat in West Town
Bright & Spacious Boho Oasis: A Warm Retreat
1 bedroom, 1 bed, 1 bathroom
29 Nov – 4 Dec
5.0 out of 5 average rating, 28 reviews
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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 135 reviews
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Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
8–13 Nov
4.95 out of 5 average rating, 111 reviews