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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
The Roscoe Village Guesthouse
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
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4.91 out of 5 average rating, 205 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.95 out of 5 average rating, 119 reviews
Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 58 reviews
Top guest favourite
Flat in Chicago
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
Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
2 bedrooms, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Chicago
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
Guest favourite
Room in Chicago
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
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Place to stay in Chicago
Woodlawn Beauty: Room 2
3 bedrooms, 3 queen beds, 1 bathroom
3–8 Aug
4.4 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Forest Park
1 bedroom garden apartment in Forest Park
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 186 reviews
Guest favourite
Flat in Chicago
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
Home in Chicago
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 Chicago
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
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.92 out of 5 average rating, 529 reviews
Top guest favourite
Apartment in Chicago
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
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
Home in Chicago
Modern Cozy Studio Near Dining & Transit
1 king bed, 1 bathroom
8–13 Aug
New place to stay