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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms, 3 beds, 2 private bathrooms
8–13 Nov
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4.99 out of 5 average rating, 141 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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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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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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Flat in 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 Chicago
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 Chicago
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 Chicago
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 Chicago
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
Bungalow in Chicago
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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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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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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Top guest favourite
Flat in Chicago
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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Guest favourite
Apartment in Chicago
Ultimate Group Experience Entire Building Chicago
9 bedrooms, 15 beds
20–25 Sept
4.8 out of 5 average rating, 10 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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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
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Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
28 Sept – 3 Oct
4.88 out of 5 average rating, 445 reviews
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Superhost
Flat in 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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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
6–11 Sept
4.95 out of 5 average rating, 88 reviews