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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Guest suite in Lake View
Wrigleyville/Boystown/Entire Private Floor!
1 bedroom, 3 beds, 1 private bathroom
29 Nov – 4 Dec
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4.86 out of 5 average rating, 292 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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Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
5.0 out of 5 average rating, 13 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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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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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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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
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 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
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
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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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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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
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Nov
4.95 out of 5 average rating, 318 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
Room in Irving Park
Al's Oasis Chicago
1 queen bed, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 244 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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Top guest favourite
Flat in Logan Square
The Logan Greystone
3 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.98 out of 5 average rating, 84 reviews
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Superhost
Flat in West Side
Bright Boutique Designer Unit in Vibrant Pilsen
1 bedroom, 1 single bed, 1 bathroom
15–20 Nov
5.0 out of 5 average rating, 3 reviews