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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Downtown Chicago
Chicago Vintage & Chic Living
2 bedrooms, 2 beds, 1 private bathroom
12–17 Oct
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4.98 out of 5 average rating, 66 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.97 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
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 34 reviews
Guest favourite
Flat in South Side
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 28 reviews
Superhost
Flat in West Side
Easy Downtown Access from Cozy Pilsen Nest
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.93 out of 5 average rating, 70 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, 14 reviews
Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
New place to stay
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
28 Nov – 3 Dec
4.96 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 253 reviews
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
23–28 Sept
5.0 out of 5 average rating, 10 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, 61 reviews
Guest favourite
Flat in Ravenswood
Stylish Modern-Chic Apartment in Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Nov
4.95 out of 5 average rating, 235 reviews
Guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
24–29 Nov
4.93 out of 5 average rating, 150 reviews
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 27 reviews