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Search results; Over 1,000 homes in Chicago

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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 126 reviews
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Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed, 1 bathroom
1–6 Dec
4.94 out of 5 average rating, 448 reviews
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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 177 reviews
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 109 reviews
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Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 44 reviews
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Top guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 229 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.99 out of 5 average rating, 364 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 363 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, 175 reviews
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Top guest favourite
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, 61 reviews
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Superhost
Guest suite in Chicago
Patio + FirePit • Park Free • Near Train & Dogs OK
2 bedrooms, 2 queen beds, 1 bathroom
3–8 Oct
New place to stay
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Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.92 out of 5 average rating, 544 reviews
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Top guest favourite
Apartment in Chicago
Welcoming 2BR in Chicago's Best Neighborhood!
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.85 out of 5 average rating, 365 reviews
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Superhost
Flat in Chicago
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
1 bedroom, 3 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 3 reviews