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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Lake View
Int. Designer’s Lakeview Duplex w/private backyard
2 bedrooms, 2 beds, 2 private bathrooms
25–30 Oct
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4.99 out of 5 average rating, 216 reviews
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Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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Guest favourite
Flat in Downtown Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
20–25 Sept
4.92 out of 5 average rating, 38 reviews
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Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 13 reviews
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Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
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Guest favourite
Flat in Downtown Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 26 reviews
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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
6–11 Sept
New place to stay
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Top guest favourite
Flat in Ukrainian Village
Stylish & Spacious Multi-Level Apt in Wicker Park
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Wicker Park
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.94 out of 5 average rating, 16 reviews
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Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
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Top guest favourite
Flat in South Side
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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Guest favourite
Townhouse in West Side
Walk to United Center 9 mins-Downtown Free Parking
3 bedrooms, 3 beds
26 Sept – 1 Oct
4.89 out of 5 average rating, 19 reviews
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Top guest favourite
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
18–23 Sept
5.0 out of 5 average rating, 6 reviews