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Search results; Over 1,000 homes in Chicago

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Superhost
Flat in Chicago
Cozy Spacious Condo Sleeps 6
2 bedrooms, 2 beds, 1 private bathroom
8–13 Nov
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4.87 out of 5 average rating, 318 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 queen beds
27 Sept – 2 Oct
New place to stay
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 queen beds
1–6 Nov
New place to stay
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Home in Forest Park
Ferdinand Front Home
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 queen beds
26–31 Dec
New place to stay
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Superhost
Flat in Chicago
Pilsen Stay | Primary King | Mins to downtown
3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 queen beds
21–26 Oct
5.0 out of 5 average rating, 30 reviews
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Flat in Chicago
Luxury penthouse with city views
4 beds
20–25 Sept
New place to stay
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Home in Berwyn
Essential Berwyn Bungalow
4 beds
20–25 Oct
New place to stay
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
2 beds
2–7 Jan
4.99 out of 5 average rating, 117 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
8 beds
19–24 Sept
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Room in Forest Park
Stay with Jeanine
Cozy City Get-away on Marengo
12–17 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
5 beds
7–12 Nov
4.9 out of 5 average rating, 529 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 beds
15–20 Nov
5.0 out of 5 average rating, 34 reviews
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Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
4 beds
28 Sept – 3 Oct
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 beds
25–30 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Flat in Chicago
Andersonville Living
5 beds
2–7 Nov
4.94 out of 5 average rating, 500 reviews