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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Loft in Chicago
Lovely Garden Studio in Chicago
1 bedroom, 1 bed, 1 private bathroom
28 Sept – 3 Oct
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4.99 out of 5 average rating, 156 reviews
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Apartment in Chicago
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
22–27 Nov
4.97 out of 5 average rating, 921 reviews
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Flat in Chicago
Private studio near Wrigley
1 bedroom, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.93 out of 5 average rating, 153 reviews
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Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 39 reviews
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Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds, 1 bathroom
20–25 Sept
New place to stay
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Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 959 reviews
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Room in Chicago
Spacious garden level suite
1 queen bed, 1 bathroom
4–9 Jan
4.96 out of 5 average rating, 324 reviews
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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
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Apartment in Chicago
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds, 1 bathroom
29 Nov – 4 Dec
4.99 out of 5 average rating, 171 reviews
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Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds, 3 bathrooms
6–11 Sept
4.95 out of 5 average rating, 111 reviews
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Flat in Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 65 reviews
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Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
4.92 out of 5 average rating, 74 reviews
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Room in Chicago
En Suite Private Queen Bedroom/Bathroom
1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 273 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
4.95 out of 5 average rating, 171 reviews
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Rooms in Oak Park
Single bedroom with Asian decor in family home
2 bedrooms, 1 double bed, 1 bathroom
18–23 Oct
4.94 out of 5 average rating, 395 reviews
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Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 57 reviews
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Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds, 1 bathroom
3–8 Dec
5.0 out of 5 average rating, 40 reviews
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Room in Chicago
Urban sanctuary retreat room 2
1 double bed, 1.5 bathrooms
21–26 Sept
New place to stay