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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Home in Chicago
Soak Up Mid-Century Style in Wrigleyville and Boystown
3 bedrooms, 5 beds, 3.5 private bathrooms
20–25 Sept
,
4.89 out of 5 average rating, 160 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
26–31 Dec
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
26–31 Oct
4.99 out of 5 average rating, 364 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
1–6 Nov
4.9 out of 5 average rating, 126 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, 109 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, 177 reviews
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Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.98 out of 5 average rating, 44 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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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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Top guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
1 bedroom, 1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 230 reviews
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Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Flat in Chicago
Bright Apartment
1 bedroom, 2 beds
7–12 Dec
4.91 out of 5 average rating, 152 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 363 reviews
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Guest favourite
Room in Chicago
Quaint Cozy Vintage for two in Lincoln Park
1 queen bed
9–14 Nov
4.9 out of 5 average rating, 68 reviews
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Superhost
Guest suite in Chicago
Patio + FirePit • Park Free • Near Train & Dogs OK
2 bedrooms, 2 queen beds
3–8 Oct
New place to stay
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Top guest favourite
Flat in Chicago
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 324 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
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Top guest favourite
Flat in Chicago
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds
3–8 Jan
4.98 out of 5 average rating, 258 reviews