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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
1 bedroom, 2 beds, 1.5 private bathrooms
24–29 Oct
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4.98 out of 5 average rating, 272 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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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, 34 reviews
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Guest favourite
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, 13 reviews
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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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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, 58 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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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, 46 reviews
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Top 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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Room in Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds
1–6 Sept
New place to stay
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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
6–11 Sept
4.96 out of 5 average rating, 89 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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Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
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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, 97 reviews
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Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.92 out of 5 average rating, 206 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Flat in Chicago
Sports Fans Welcome and Family Friendly
3 bedrooms, 8 beds
29 Sept – 4 Oct
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds
17–22 Sept
4.92 out of 5 average rating, 258 reviews
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Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds
22–27 Oct
4.91 out of 5 average rating, 11 reviews