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Search results; Over 1,000 homes in Chicago

Guest favourite
Guest suite in Chicago
Private Chicago Getaway
1 bedroom, 1 bed, 1 private bathroom
20–25 Oct
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4.86 out of 5 average rating, 57 reviews
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
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
4–9 Oct
4.98 out of 5 average rating, 168 reviews
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, 59 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 6 reviews
Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
1–6 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 62 reviews
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, 14 reviews
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, 207 reviews
Top guest favourite
Flat in Oak Park
Oak Park Chic Duplex King Bed, Parking, Deck, Yard
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 98 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
7–12 Sept
New place to stay
Guest favourite
Home in Chicago
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
8–13 Nov
4.95 out of 5 average rating, 195 reviews
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, 80 reviews
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