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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Sunny Treetop Oasis in Roscoe Village - 1BR/1BA
1 bedroom, 1 bed, 1 private bathroom
28 Sept – 3 Oct
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5.0 out of 5 average rating, 94 reviews
Superhost
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 122 reviews
Superhost
Apartment in Chicago
Vintage Meets Modern in Logan Square
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
Guest favourite
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
20–25 Sept
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
19–24 Aug
5.0 out of 5 average rating, 17 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 25 reviews
Flat in Chicago
Art & Soul in Logan Square|4BR Walk to Blue Line
4 bedrooms, 4 beds, 1.5 bathrooms
17–22 Aug
New place to stay
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, 359 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds, 2 bathrooms
16–21 Aug
4.91 out of 5 average rating, 43 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
17–22 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
11–16 Nov
4.96 out of 5 average rating, 309 reviews
Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
2–7 Nov
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Apartment in Chicago
Wrigleyville Updated Condo with Free Parking
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.99 out of 5 average rating, 105 reviews
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews