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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in Downtown Chicago
Modern 3BR with Private Rooftop & Free Parking
3 bedrooms, 7 beds, 2.5 private bathrooms
4–9 Oct
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4.92 out of 5 average rating, 186 reviews
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Featured hotel
Room in Downtown Chicago
Studio suite
6–11 Sept
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Featured hotel
Room in Downtown Chicago
Level studio suite
3–8 Oct
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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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Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 132 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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Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds
17–22 Sept
4.92 out of 5 average rating, 60 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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Top guest favourite
Flat in Logan Square
Prime Logan Square apartment
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 43 reviews
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Flat in Downtown Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
6–11 Sept
New place to stay
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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 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 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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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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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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Superhost
Flat in West Side
Bright Boutique Designer Unit in Vibrant Pilsen
1 bedroom, 1 single bed
20–25 Sept
New place to stay
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Featured hotel
Room in Downtown Chicago
Deluxe king non smoking
1 king bed
6–11 Sept
4.91 out of 5 average rating, 11 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
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Top guest favourite
Flat in Lake View
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 361 reviews