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Search results; Over 1,000 homes in Chicago

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Guest favourite
Apartment in Bridgeport
Convenient & Spacious 3BR Condo w/Free Parking
3 bedrooms, 5 beds, 2 private bathrooms
1–6 Nov
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4.9 out of 5 average rating, 160 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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Top guest favourite
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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Top guest favourite
Flat in Uptown
Private studio near Wrigley
1 bedroom, 2 beds
29 Nov – 4 Dec
4.93 out of 5 average rating, 154 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
Flat in Ukrainian Village
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds
25–30 Oct
4.98 out of 5 average rating, 253 reviews
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Top guest favourite
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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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, 58 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
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Lake View
Furnished Lakeview Studio Near Wrigley Field
1 queen bed
24–29 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Logan Square
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 14 reviews
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Room in Downtown Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds
20–25 Sept
New place to stay
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Guest favourite
Room in Irving Park
Cozy Room for One In The Company of Cats -Blueline
1 single bed
24–29 Nov
4.93 out of 5 average rating, 149 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
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
16–21 Nov
4.95 out of 5 average rating, 171 reviews
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Top guest favourite
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
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
25–30 Oct
4.97 out of 5 average rating, 73 reviews