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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Ukrainian Village
Bright, Modern Apartment in a Vintage Greystone
1 bedroom, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.92 out of 5 average rating, 441 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
21–26 Oct
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
11–16 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Humboldt Park
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 West Town
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds
26–31 Oct
4.96 out of 5 average rating, 143 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 962 reviews
Top guest favourite
Flat in Logan Square
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 109 reviews
Top guest favourite
Flat in North Side
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
Flat in West Town
Spacious & New Industrial Condo Close to Downtown
3 bedrooms, 4 queen beds
4–9 Oct
4.9 out of 5 average rating, 302 reviews
Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews
Guest favourite
Flat in Downtown Chicago
Gold Coast Luxury: 2BR with Sweeping City Vistas
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 125 reviews
Superhost
Flat in Downtown Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
27 Sept – 2 Oct
New place to stay
Top guest favourite
Flat in Lake View
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed
25–30 Oct
4.93 out of 5 average rating, 195 reviews
Guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Lincoln Park
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed
5–10 Dec
5.0 out of 5 average rating, 323 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Loft 402 | River North
3 bedrooms, 3 queen beds
25–30 Oct
4.97 out of 5 average rating, 33 reviews