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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Home in Chicago
Soak Up Mid-Century Style in Wrigleyville and Boystown
3 bedrooms, 5 beds, 3.5 private bathrooms
12–17 Oct
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4.89 out of 5 average rating, 160 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds
1–6 Nov
New place to stay
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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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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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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 5 reviews
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Superhost
Flat in Chicago
Designer Loft 3E | Heart of Gold Coast/River North
3 bedrooms, 6 beds
30 Oct – 4 Nov
New place to stay
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Home in Wood Dale
Entire 3B/2B Home in Wood Dale-Near O'Hare Airport
3 bedrooms, 3 beds
4–9 Oct
New place to stay
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Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
12–17 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorites xx
5 bedrooms, 8 beds
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
25–30 Oct
5.0 out of 5 average rating, 7 reviews
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 3 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
1–6 Nov
4.75 out of 5 average rating, 4 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, 133 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
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
25–30 Oct
5.0 out of 5 average rating, 3 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, 64 reviews
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Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
1–6 Nov
4.9 out of 5 average rating, 42 reviews
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Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds
13–18 Dec
5.0 out of 5 average rating, 13 reviews