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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Guest suite in West Town
Secret Garden @ The Noble Farmhouse | Wicker Park
Studio, 2 beds, 1 private bathroom
24–29 Oct
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4.96 out of 5 average rating, 405 reviews
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Featured hotel
Hotel in West Loop
The Emily Hotel, Deluxe double
1 bedroom, 2 double beds
1–6 Oct
4.92 out of 5 average rating, 64 reviews
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Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
8–13 Nov
4.9 out of 5 average rating, 126 reviews
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Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
8–13 Nov
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
18–23 Jan
4.95 out of 5 average rating, 318 reviews
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Guest favourite
Room in Wicker Park
Charming Room in Historic Ukrainian Village!
1 queen bed
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Flat in West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
1–6 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 76 reviews
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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 135 reviews
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Top guest favourite
Guest suite in Portage Park
Eddy Street Upstairs Apartment
1 bedroom, 1 bed
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
2–7 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest suite in North Side
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed
15–20 Nov
4.92 out of 5 average rating, 545 reviews
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Top guest favourite
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 62 reviews
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Top guest favourite
Flat in Edgewater
Andersonville Living
3 bedrooms, 5 beds
2–7 Nov
4.94 out of 5 average rating, 501 reviews
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Top guest favourite
Guest house in Irving Park
Horner Park Coach House
1 bedroom, 2 beds
11–16 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest suite in Andersonville
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed
15–20 Nov
4.96 out of 5 average rating, 417 reviews
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Top guest favourite
Guest suite in Ravenswood
Private suite in Lincoln Square
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 486 reviews