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Search results; Over 1,000 homes in Chicago

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Superhost
Loft in West Town
OHC Gorgeous Huge Studio Apt Steps to Blue Line
Studio, 3 beds, 1 private bathroom
1–6 Nov
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4.89 out of 5 average rating, 410 reviews
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Featured hotel
Hotel in West Loop
The Emily Hotel, Deluxe double
1 bedroom, 2 double beds, 1 bathroom
14–19 Oct
4.92 out of 5 average rating, 64 reviews
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Featured hotel
Hotel in The Loop
Sports Illustrated Resorts Chicago, Studio king
1 bedroom, 1 king bed, 1 bathroom
12–17 Oct
New place to stay
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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, 37 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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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
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
8–13 Nov
4.96 out of 5 average rating, 112 reviews
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Guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Jan
4.95 out of 5 average rating, 318 reviews
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Guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
2–7 Jan
4.94 out of 5 average rating, 263 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
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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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
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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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
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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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
Apartment in Wicker Park
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 171 reviews
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Top guest favourite
Flat in Wicker Park
COZY Bright*BOLD*FUN* Eclectic Wicker Park Home
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
4.97 out of 5 average rating, 187 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