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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in Wrigleyville
Can't Beat This 2min Walk to Wrigley!
2 bedrooms, 5 beds, 2 private bathrooms
29 Sept – 4 Oct
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4.81 out of 5 average rating, 280 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
9–14 Aug
4.77 out of 5 average rating, 568 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
4.95 out of 5 average rating, 119 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
13–18 Aug
4.91 out of 5 average rating, 58 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
Room in Irving Park
Lovely Front Room in a New Renovated Apartment
2 single beds, 1 bathroom
22–27 Sept
4.91 out of 5 average rating, 103 reviews
Top guest favourite
Flat in West Town
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 616 reviews
Guest favourite
Flat in Downtown Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 22 reviews
Superhost
Place to stay in South Side
Woodlawn Beauty: Room 2
3 bedrooms, 3 queen beds, 1 bathroom
3–8 Aug
4.5 out of 5 average rating, 6 reviews
Top guest favourite
Room in West Side
Spacious & serene in hip spot. Sleeps 4.
1 queen bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 521 reviews
Top guest favourite
Apartment in Lake View
Bright, new 2BR in the heart of East Lakeview
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 128 reviews
Guest favourite
Flat in Portage Park
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 51 reviews
Top 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, 234 reviews
Top 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
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
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 Lake View
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 348 reviews
Place to stay in Chicago
Guest room in Dunning, Chicago IL
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
New place to stay