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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Stylish First Flr. Studio. Best Location Division+Hermitage.
1 bedroom, 1 bed, 1 private bathroom
23–28 Nov
,
4.97 out of 5 average rating, 313 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
24–29 Oct
4.75 out of 5 average rating, 4 reviews
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Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds
13–18 Dec
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 35 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
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Superhost
Flat in Chicago
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds
12–17 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in Chicago
Private suite in Lincoln Square
1 bedroom, 1 queen bed
18–23 Oct
4.97 out of 5 average rating, 485 reviews
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Top guest favourite
Flat in Chicago
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed
1–6 Nov
4.93 out of 5 average rating, 196 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
15–20 Nov
4.99 out of 5 average rating, 363 reviews
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Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed
1–6 Dec
4.94 out of 5 average rating, 448 reviews
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Flat in Chicago
Rustic Sanctuary
2 bedrooms, 2 queen beds
1–6 Oct
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed
2–7 Nov
4.94 out of 5 average rating, 178 reviews
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Room in Chicago
Private Twin Bedroom with Private Bathroom
2 single beds
11–16 Oct
4.96 out of 5 average rating, 212 reviews
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Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Apartment in Chicago
Welcoming 2BR in Chicago's Best Neighborhood!
2 bedrooms, 2 beds
1–6 Nov
4.85 out of 5 average rating, 365 reviews
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Flat in Chicago
Stylish 2BR with Balcony Near Lake & Downtown
2 bedrooms, 2 queen beds
17–22 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Chicago
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed
5–10 Dec
5.0 out of 5 average rating, 325 reviews