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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Susie's Space. 2BR easy parking & pet friendly
2 bedrooms, 2 beds, 1 private bathroom
28 Oct – 2 Nov
,
4.92 out of 5 average rating, 396 reviews
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Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
6–11 Dec
4.97 out of 5 average rating, 635 reviews
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 111 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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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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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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Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed
25–30 Oct
4.96 out of 5 average rating, 515 reviews
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Flat in Chicago
Cozy Chicago Studio | Washer, Near Transit & Eat
1 queen bed
24–29 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed
15–20 Nov
4.96 out of 5 average rating, 417 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed
5–10 Nov
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 5 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
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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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
Bright & Spacious Boho Oasis: A Warm Retreat
1 bedroom, 1 bed
29 Nov – 4 Dec
5.0 out of 5 average rating, 28 reviews
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Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds
2–7 Nov
4.94 out of 5 average rating, 500 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
Room in Chicago
Al's Oasis Chicago
1 queen bed
18–23 Oct
4.96 out of 5 average rating, 244 reviews