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Search results; Over 1,000 homes in Chicago

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Superhost
Hotel in Chicago Loop
A polished, modern affair on iconic Michigan Ave.
1 bedroom, 1 bed, 1 private bathroom
1–6 Sept
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4.82 out of 5 average rating, 704 reviews
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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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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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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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Flat in Downtown Chicago
Chic 4BR South Loop Urban Retreat Near McCormick
4 bedrooms, 5 beds
8–13 Sept
New place to stay
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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, 12 reviews
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Superhost
Flat in Bridgeport
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 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, 130 reviews
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Guest favourite
Flat in Wicker Park
Spacious 3bd/3ba Apt in West Town - Next to Kasama
3 bedrooms, 3 beds
21–26 Sept
4.9 out of 5 average rating, 30 reviews
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
6–11 Sept
5.0 out of 5 average rating, 57 reviews
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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
Bungalow in Beverly
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.95 out of 5 average rating, 44 reviews
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Superhost
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, 11 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, 25 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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Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
20–25 Sept
4.91 out of 5 average rating, 11 reviews
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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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Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
6–11 Sept
4.95 out of 5 average rating, 88 reviews
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Guest favourite
Apartment in Bronzeville
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
20–25 Sept
4.8 out of 5 average rating, 10 reviews