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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in West Loop
Pro Cleaned & Isolated West Loop Coach House
1 bedroom, 2 beds, 1 private bathroom
9–14 Aug
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4.87 out of 5 average rating, 492 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 907 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.92 out of 5 average rating, 59 reviews
Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
29 Aug – 3 Sept
4.96 out of 5 average rating, 300 reviews
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 235 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in South Side
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, 22 reviews
Guest favourite
Home in Ukrainian Village
West Town Gem: 2BR w/ Patio, W/D + Free Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
2 bedrooms, 2 queen beds, 1 bathroom
16–21 Aug
4.77 out of 5 average rating, 568 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 113 reviews
Top guest favourite
Flat in Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.98 out of 5 average rating, 131 reviews
Guest favourite
Room in Irving Park
Lovely Front Room #1 in a New Renovated Apartment
2 single beds, 1 bathroom
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Place to stay in West Side
Private Room w/ Attached Bathroom
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
New place to stay
Top guest favourite
Flat in West Side
Great place in the Heart of Pilsen
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Place to stay in West Side
BOHEMIAN LODGE #3 ( clean & affordable travel)
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.87 out of 5 average rating, 237 reviews
Top guest favourite
Guest suite in Ravenswood
Private Lincoln Square Garden Apt
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.92 out of 5 average rating, 490 reviews