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Search results; Over 1,000 homes in Chicago

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Guest favourite
Apartment in Chicago
The Bright Retreat in Andersonville
1 bedroom, 2 beds, 1 private bathroom
31 Oct – 5 Nov
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4.86 out of 5 average rating, 253 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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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds
20–25 Oct
New place to stay
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
26–31 Dec
New place to stay
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Top guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 141 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
21–26 Oct
5.0 out of 5 average rating, 30 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, 61 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
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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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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
15–20 Nov
5.0 out of 5 average rating, 34 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, 529 reviews
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Superhost
Flat in Chicago
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
1 bedroom, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 3 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
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds
24–29 Oct
4.95 out of 5 average rating, 110 reviews
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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, 6 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, 12 reviews
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Top guest favourite
Flat in Oak Park
Space & Style Near Downtown Parking+Walk To It All
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 101 reviews