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Search results; Over 1,000 homes in Chicago

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Superhost
Hotel room in Wicker Park
Sun-Filled King Room in Boutique Wicker Park B&B
1 bedroom, 1 bed, 2 private bathrooms
11–16 Dec
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5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
8–13 Nov
4.9 out of 5 average rating, 126 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, 4 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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Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 7 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
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 112 reviews
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Guest favourite
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 62 reviews
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Superhost
Flat in Downtown Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Nov
New place to stay
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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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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, 136 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 Edgewater
Andersonville Living
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 501 reviews
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Top guest favourite
Guest suite in North Side
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 545 reviews
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Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 2 beds, 1 bathroom
11–16 Nov
5.0 out of 5 average rating, 14 reviews
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Superhost
Flat in West Side
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Guest suite in Ravenswood
Private suite in Lincoln Square
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 487 reviews
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Top guest favourite
Flat in Lake View
Charming, Spacious 3BR Lakeview Apt Near Transit
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 461 reviews