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Search results; Over 1,000 homes in Chicago

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Guest favourite
Guest suite in Chicago
The Drake - Chic 2BR Private Unit
2 bedrooms, 2 beds, 1 private bathroom
31 Oct – 5 Nov
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4.83 out of 5 average rating, 162 reviews
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Top guest favourite
Flat in Chicago
Private studio near Wrigley
1 bedroom, 2 beds
29 Nov – 4 Dec
4.93 out of 5 average rating, 153 reviews
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Top guest favourite
Flat in Chicago
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 Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds
15–20 Nov
4.97 out of 5 average rating, 38 reviews
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Superhost
Room in Chicago
Private RM 1st FLR BDRM|12”Memory Queen BD|TV|Fan
1 queen bed
1–6 Nov
4.95 out of 5 average rating, 57 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Home in Chicago
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 Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 57 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 03 - Terrace - River North
3 bedrooms, 7 beds
6–11 Sept
4.95 out of 5 average rating, 110 reviews
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Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
3–8 Dec
5.0 out of 5 average rating, 39 reviews
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Superhost
Room in Chicago
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 Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 61 reviews
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Superhost
Apartment in Chicago
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 Chicago
Bright & Chic Retreat Steps from Lincoln Square
2 bedrooms, 2 queen beds
1–6 Nov
5.0 out of 5 average rating, 65 reviews
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Guest favourite
Home in Chicago
Chicago Row House Garden Apartmt
1 bedroom, 1 bed
26–31 Oct
4.92 out of 5 average rating, 74 reviews
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Top guest favourite
Home in Chicago
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 Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds
7–12 Nov
4.9 out of 5 average rating, 520 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 170 reviews
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Superhost
Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 59 reviews