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Search results; Over 1,000 homes in Chicago

Descriptions are based on details hosts provide
Top guest favourite
Flat in Chicago
Modern vintage chic steps from Wrigley: park free
3 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
,
4.96 out of 5 average rating, 271 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 121 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Guest favourite
Home in Chicago
Patio with swing chairs near United Center
4.9 out of 5 average rating, 60 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
5.0 out of 5 average rating, 49 reviews, 2 bedrooms, 2 beds, 2 bathrooms
25–30 Oct
Top guest favourite
Flat in Chicago
Loft with a baby grand and game room
4.96 out of 5 average rating, 26 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
Top guest favourite
Flat in Chicago
1888 cottage with an 85-inch TV
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Top guest favourite
Home in Chicago
1908 coach house with rooftop skyline views
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Guest favourite
Apartment in Chicago
Newly renovated top floor in Avondale
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Guest favourite
Flat in Chicago
Open-concept flat with a private patio
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 236 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Flat in Chicago
Free parking and a home gym
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Chicago
West Town Gem: 2BR w/ Patio, W/D + Free Parking
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Flat in Chicago
Modern Luxe Retreat in Pilsen’s Colorful Center
5.0 out of 5 average rating, 43 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Flat in Chicago
Vintage Ukrainian Village Apartment
4.95 out of 5 average rating, 186 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Nov
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 113 reviews, 3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Chicago
Great place in the Heart of Pilsen
4.96 out of 5 average rating, 23 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
Guest favourite
Room in Chicago
Lovely Front Room #1 in a New Renovated Apartment
4.91 out of 5 average rating, 103 reviews, 2 single beds, 1 bathroom
22–27 Sept
Top guest favourite
Flat in Chicago
Sun-filled top floor near 606 trail
4.77 out of 5 average rating, 569 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Forest Park
A treetop coach house near Oak Park
5.0 out of 5 average rating, 375 reviews, 1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct