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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest suite in Lincoln Square
Great location, private entry and patio!
1 bedroom, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 347 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
12–17 Oct
4.95 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
14–19 Sept
4.97 out of 5 average rating, 65 reviews
Top guest favourite
Flat in West Side
Modern Luxe Retreat in Pilsen’s Colorful Center
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 43 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in West Town
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
4–9 Oct
4.98 out of 5 average rating, 617 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in North Side
Quiet & Modern Avondale Apartment
2 bedrooms, 2 beds
6–11 Sept
4.7 out of 5 average rating, 10 reviews
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds
16–21 Aug
4.77 out of 5 average rating, 569 reviews
Guest favourite
Room in Irving Park
Lovely Front Room #1 in a New Renovated Apartment
2 single beds
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Superhost
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
13–18 Sept
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds
21–26 Sept
4.98 out of 5 average rating, 131 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in West Side
Great place in the Heart of Pilsen
2 bedrooms, 2 beds
15–20 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds
8–13 Nov
4.96 out of 5 average rating, 589 reviews