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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in West Town
The Woodsman's Gallery at OHC
3 bedrooms, 4 beds, 2 private bathrooms
19–24 Sept
,
4.9 out of 5 average rating, 630 reviews
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Flat in West Town
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
9–14 Nov
4.97 out of 5 average rating, 630 reviews
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Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
New place to stay
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Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds
6–11 Dec
4.99 out of 5 average rating, 959 reviews
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Flat in North Side
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 39 reviews
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Flat in Irving Park
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
3–8 Dec
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Flat in Little Italy
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
21–26 Oct
5.0 out of 5 average rating, 57 reviews
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Top guest favourite
Apartment in Lincoln Park
Bright and Sunny 2 BR Condo - Wrigley/Lincoln Park
2 bedrooms, 2 beds
29 Nov – 4 Dec
4.99 out of 5 average rating, 171 reviews
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Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Room in Downtown Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
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Top guest favourite
Flat in Edgewater
Cozy Garden Unit In Edgewater
1 bedroom, 2 beds
29 Nov – 4 Dec
4.86 out of 5 average rating, 475 reviews
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Top guest favourite
Flat in Downtown Chicago
2br/2ba, A+ location by Mag mile, views & spacious
2 bedrooms, 4 beds
25–30 Oct
4.94 out of 5 average rating, 381 reviews
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Guest favourite
Home in West Side
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
23–28 Oct
4.92 out of 5 average rating, 74 reviews
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Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds
1–6 Nov
4.97 out of 5 average rating, 39 reviews
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Flat in Logan Square
Chic & Cozy Boho Vibe in Heart of Logan Square
2 bedrooms, 2 queen beds
28 Nov – 3 Dec
4.96 out of 5 average rating, 83 reviews
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Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed
4–9 Jan
4.96 out of 5 average rating, 324 reviews
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Top guest favourite
Flat in West Town
Bright & Spacious Boho Oasis: A Warm Retreat
1 bedroom, 1 bed
19–24 Nov
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Apartment in Lake View
Urban Comfort in the Heart of Chicago
1 bedroom, 2 beds
8–13 Nov
4.99 out of 5 average rating, 716 reviews