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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
Pro Cleaned & Isolated West Loop Coach House
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept
,
4.87 out of 5 average rating, 495 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
7–12 Aug
New place to stay
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
27 Dec – 1 Jan
4.95 out of 5 average rating, 127 reviews
Superhost
Home in Chicago
Sleeps 15 • Game Room • Theater • Gym
7 bedrooms, 8 beds
8–13 Aug
New place to stay
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 39 reviews
Guest favourite
Room in Alsip
Safe clean charming close transportation Viva!
1 queen bed
9–14 Aug
4.91 out of 5 average rating, 274 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
9–14 Aug
4.91 out of 5 average rating, 76 reviews
Guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
6–11 Aug
4.91 out of 5 average rating, 117 reviews
Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Home in Whiting
The Ashlin House.
3 bedrooms, 3 beds
12–17 Oct
4.91 out of 5 average rating, 123 reviews
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 50 reviews
Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 24 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed
9–14 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
8–13 Aug
4.9 out of 5 average rating, 42 reviews
Top guest favourite
Flat in Chicago
Stay Above Chicago's Post-Punk Museum - 4BR Loft
4 bedrooms, 5 beds
8–13 Aug
5.0 out of 5 average rating, 29 reviews