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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
Elegant 3/BR w/Balcony by Downtown, Chinatown
3 bedrooms, 6 beds, 2 private bathrooms
20–25 Sept
,
4.81 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 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, 60 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, 188 reviews
Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 47 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, 15 reviews
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
8–13 Sept
4.33 out of 5 average rating, 3 reviews
Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 5 reviews
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, 39 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
28 Oct – 2 Nov
4.95 out of 5 average rating, 273 reviews
Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 36 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Chicago
Spacious, Charming, Top Floor, Steps to Wrigley
3 bedrooms, 4 beds, 1 bathroom
25–30 Sept
5.0 out of 5 average rating, 7 reviews
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Guest favourite
Flat in Chicago
Penthouse Designer Loft 4W | GoldCoast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Oct
5.0 out of 5 average rating, 14 reviews
Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds, 2 bathrooms
22–27 Oct
4.89 out of 5 average rating, 80 reviews
Top guest favourite
Apartment in Chicago
Superiorhaus Noble Square Sleeps 16 HotTub/RecRoom
4 bedrooms, 11 beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 81 reviews