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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in Chicago
The Woodsman's Gallery at OHC
3 bedrooms, 4 beds, 2 private bathrooms
29 Oct – 3 Nov
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4.91 out of 5 average rating, 633 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds
8–13 Nov
4.9 out of 5 average rating, 126 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
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
8–13 Nov
5.0 out of 5 average rating, 36 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, 112 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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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
1–6 Nov
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 135 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, 12 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
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 76 reviews
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Superhost
Flat in Chicago
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 263 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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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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Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
1–6 Nov
New place to stay
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Top guest favourite
Apartment in Chicago
Two Bedroom w Porch in Wicker Park
2 bedrooms, 2 beds
9–14 Nov
4.96 out of 5 average rating, 123 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, 486 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