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Search results; Over 1,000 homes in Chicago

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Guest favourite
Apartment in Chicago
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
2 bedrooms, 3 beds, 3 private bathrooms
12–17 Oct
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4.84 out of 5 average rating, 177 reviews
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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, 35 reviews
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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, 365 reviews
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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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Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 110 reviews
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Room in Chicago
Private Twin Bedroom with Private Bathroom
2 single beds, 2.5 bathrooms
11–16 Oct
4.96 out of 5 average rating, 212 reviews
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Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds, 1 bathroom
7–12 Jan
4.99 out of 5 average rating, 118 reviews
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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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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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Room in Chicago
Quaint Cozy Vintage for two in Lincoln Park
1 queen bed, 1 bathroom
9–14 Nov
4.9 out of 5 average rating, 68 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, 61 reviews
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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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Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
1 bedroom, 2 beds, 1 bathroom
13–18 Dec
4.96 out of 5 average rating, 608 reviews
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Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 500 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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Guest suite in Chicago
Private Lincoln Square Garden Apt
1 bedroom, 1 queen bed, 1 bathroom
2–7 Nov
4.92 out of 5 average rating, 500 reviews
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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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Guest suite in Chicago
Wrigleyville/Boystown/Entire Private Floor!
1 bedroom, 3 beds, 1 bathroom
29 Nov – 4 Dec
4.86 out of 5 average rating, 291 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