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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Lake View
Int. Designer’s Lakeview Duplex w/private backyard
2 bedrooms, 2 beds, 2 private bathrooms
25–30 Oct
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4.99 out of 5 average rating, 216 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
26–31 Oct
4.92 out of 5 average rating, 74 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 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, 14 reviews
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 reviews
Guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Flat in West Side
Chicago Stay *Steps to Viral La Catedral Café*
2 bedrooms, 2 beds
6–11 Sept
New place to stay
Top guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds
25–30 Oct
4.98 out of 5 average rating, 253 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
Guest favourite
Flat in South Side
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 74 reviews
Room in Downtown Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds
6–11 Sept
New place to stay
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 312 reviews
Guest favourite
Flat in Ravenswood
Stylish Modern-Chic Apartment in Lincoln Square
2 bedrooms, 2 queen beds
15–20 Nov
4.95 out of 5 average rating, 235 reviews
Guest favourite
Apartment in South Side
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.88 out of 5 average rating, 78 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 28 reviews
Flat in West Side
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay