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Search results; Over 1,000 homes in Chicago

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, 74 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 46 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed•Parking•Deck•Yard
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 97 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
6–11 Sept
4.96 out of 5 average rating, 89 reviews
Top guest favourite
Flat in Chicago
Sports Fans Welcome and Family Friendly
3 bedrooms, 8 beds, 2 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Evanston
New 3bd/1.5 bth Apt w/private prkg
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.92 out of 5 average rating, 206 reviews
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds, 3.5 bathrooms
24–29 Sept
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 32 reviews
Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
Room in Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds, 1 bathroom
20–25 Sept
New place to stay
Flat in Chicago
Luxury | Gym | Balcony - NOT
2 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
New place to stay
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 8 reviews