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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Guest suite in Chicago
Cozy Andersonville Cabin
1 bedroom, 2 beds, 1 private bathroom
24 Feb – 1 Mar
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4.98 out of 5 average rating, 175 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
2–7 Jan
4.75 out of 5 average rating, 4 reviews
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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
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 136 reviews
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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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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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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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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
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds
16–21 Nov
5.0 out of 5 average rating, 62 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, 171 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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Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
4 bedrooms, 4 beds
24–29 Oct
5.0 out of 5 average rating, 26 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, 65 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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Guest favourite
Flat in Chicago
Spacious, Charming, Top Floor, Steps to Wrigley
3 bedrooms, 4 beds
4–9 Oct
4.56 out of 5 average rating, 9 reviews
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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 112 reviews
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed
5–10 Nov
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds
11–16 Nov
4.93 out of 5 average rating, 58 reviews