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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Downtown Chicago
Penthouse Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
30 Sept – 5 Oct
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4.78 out of 5 average rating, 239 reviews
Featured hotel
Hotel in Downtown Chicago
Level studio suite
1 bedroom, 1 bathroom
21–26 Oct
Featured hotel
Hotel in Downtown Chicago
Junior two bedroom suite
2 bedrooms, 1 bathroom
18–23 Oct
Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds, 1 bathroom
23–28 Sept
4.92 out of 5 average rating, 62 reviews
Guest favourite
Flat in West Town
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
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Little Italy
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
Top guest favourite
Flat in West Town
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
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3 bathrooms
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Lincoln Park
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 324 reviews
Guest favourite
Flat in West Side
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
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 962 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Flat in West Town
Modern & Spacious Condo Minutes from the Loop
3 bedrooms, 3 queen beds, 2 bathrooms
28 Nov – 3 Dec
4.97 out of 5 average rating, 95 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
3–8 Nov
4.95 out of 5 average rating, 111 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 925 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 33 reviews
Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews