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Search results; Over 1,000 homes in Chicago

Guest favourite
Flat in Downtown Chicago
Chic Corner 2BR in Streeterville | Roof Deck
2 bedrooms, 3 beds, 1 private bathroom
8–13 Aug
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4.76 out of 5 average rating, 221 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
4.91 out of 5 average rating, 58 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 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 West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
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
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
Apartment in Lake View
Bright, new 2BR in the heart of East Lakeview
4.99 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
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
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
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
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
Top guest favourite
Flat in Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
4.99 out of 5 average rating, 349 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Guest suite in Ravenswood
Private Lincoln Square Garden Apt
4.92 out of 5 average rating, 490 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Nov
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
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top 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
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
4.92 out of 5 average rating, 51 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Sept