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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Home in Chicago
Wrigleyville Greystone
3 bedrooms, 3 beds, 2 private bathrooms
4–9 Oct
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4.95 out of 5 average rating, 227 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Dec
New place to stay
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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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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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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Nov
4.95 out of 5 average rating, 133 reviews
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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
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
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds, 1 bathroom
12–17 Oct
4.91 out of 5 average rating, 542 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
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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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Dec
4.97 out of 5 average rating, 76 reviews
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Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
2–7 Jan
4.99 out of 5 average rating, 117 reviews
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Flat in Chicago
Cozy Chicago Studio | Washer, Near Transit & Eat
1 queen bed, 1 bathroom
1–6 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Guest suite in Chicago
Great location, private entry and patio!
1 bedroom, 3 beds, 1 bathroom
9–14 Dec
4.96 out of 5 average rating, 357 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
Flat in Chicago
Charming, Spacious 3BR Lakeview Apt Near Transit
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 460 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