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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Chicago
Wrigleyville/Boystown/Entire Private Floor!
1 bedroom, 3 beds, 1 private bathroom
29 Nov – 4 Dec
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4.85 out of 5 average rating, 289 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds
8–13 Sept
New place to stay
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
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, 60 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 168 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 36 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
8–13 Sept
4.96 out of 5 average rating, 47 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 29 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
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 108 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
12–17 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 172 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
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, 23 reviews
Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 41 reviews
Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
4–9 Oct
5.0 out of 5 average rating, 5 reviews