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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Lake View
Modern vintage chic steps from Wrigley: park free
3 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.96 out of 5 average rating, 271 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
4.97 out of 5 average rating, 906 reviews, 1 bedroom, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Flat in Little Italy
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 North Side
Avondale Creative Loft | King Bed•Games•Parking
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
4.96 out of 5 average rating, 300 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 Dec
Guest favourite
Room in Irving Park
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
Guest favourite
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Flat in Logan Square
Sun filled tranquil 2 br great part of Logan Sq.
4.77 out of 5 average rating, 568 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Ukrainian Village
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
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 Bridgeport
Sunny Cozy Spacious Boho-Chic Condo in Bridgeport
4.98 out of 5 average rating, 131 reviews, 2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
4.93 out of 5 average rating, 235 reviews, 2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
Guest favourite
Room in West Side
near festivals & united center
4.95 out of 5 average rating, 115 reviews, 1 bed, 1 bathroom
30 Sept – 5 Oct
Top guest favourite
Flat in West Side
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
Top guest favourite
Flat in Chicago Loop
Spacious 1-bedroom South Loop Loft I Sleep 5
4.94 out of 5 average rating, 234 reviews, 1 bedroom, 4 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Wicker Park
City Chickens Studio
4.96 out of 5 average rating, 233 reviews, 1 bed, 1 bathroom
1–6 Nov