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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 private bathrooms
27 Sept – 2 Oct
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4.95 out of 5 average rating, 73 reviews
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Shared room in Chicago
SFH Home |
4 bedrooms, 5 beds
10–15 Sept
4.94 out of 5 average rating, 47 reviews
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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
13–18 Sept
New place to stay
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Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Flat in 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
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 57 reviews
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Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
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Superhost
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 21 reviews
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Superhost
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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Flat in Chicago
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
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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Top guest favourite
Bungalow in Chicago
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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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Top guest favourite
Flat in Oak Park
Curated & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 96 reviews
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Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
7–12 Sept
4.91 out of 5 average rating, 79 reviews
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Top guest favourite
Flat in Chicago
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
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds
29 Sept – 4 Oct
4.92 out of 5 average rating, 257 reviews