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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Best in Chicago, private, amazing garden space
2 bedrooms, 3 beds, 1 private bathroom
1–6 Nov
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4.95 out of 5 average rating, 757 reviews
Top guest favourite
Apartment in 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
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
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 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
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
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
Guest favourite
Flat in 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
Guest favourite
Flat in Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Chicago
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
Guest favourite
Flat in Chicago
Top-Floor Oasis: 2BR in Heart of Fulton Market
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.89 out of 5 average rating, 70 reviews
Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 170 reviews
Top guest favourite
Flat in Chicago
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
Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds, 2.5 bathrooms
27 Sept – 2 Oct
New place to stay
Guest favourite
Flat in Chicago
WickerPark 3BR| 5 beds|2 Parking| Damen L 4min walk
3 bedrooms, 5 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Guest house in Chicago
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, 963 reviews
Top guest favourite
Flat in Chicago
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
Top guest favourite
Flat in Chicago
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
Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 101 reviews