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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Cozy loft in Chicago's Uptown
1 bedroom, 2 beds, 1 private bathroom
26–31 Oct
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4.97 out of 5 average rating, 342 reviews
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jan
4.95 out of 5 average rating, 130 reviews
Guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 43 reviews
Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 38 reviews
Flat in Chicago
Chic 4BR South Loop Urban Retreat Near McCormick
4 bedrooms, 5 beds, 3 bathrooms
8–13 Sept
New place to stay
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
26 Sept – 1 Oct
New place to stay
Top guest favourite
Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 170 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds, 3.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 135 reviews
Home in Chicago
Beautiful Wicker Park Brownstown Unit
3 bedrooms, 3 beds, 2 bathrooms
13–18 Sept
New place to stay
Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
7–12 Nov
4.9 out of 5 average rating, 519 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, 11 reviews
Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 580 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 72 reviews
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds, 2 bathrooms
29 Sept – 4 Oct
4.88 out of 5 average rating, 76 reviews
Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
30 Sept – 5 Oct
4.98 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds, 2.5 bathrooms
8–13 Nov
4.98 out of 5 average rating, 59 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 31 reviews