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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in Chicago
Decompress on a Sophisticated Chaise at a Glamorous Hideaway
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.96 out of 5 average rating, 203 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
15–20 Nov
New place to stay
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 34 reviews
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds, 1 bathroom
20–25 Oct
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, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 133 reviews
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Guest favourite
Flat in Chicago
Luxury Designer Apartment 802| Gold Coast/Old Town
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 32 reviews
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Top guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
26–31 Oct
4.98 out of 5 average rating, 189 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, 2.5 bathrooms
11–16 Nov
5.0 out of 5 average rating, 101 reviews
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Superhost
Flat in Chicago
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
1 bedroom, 3 beds, 1 bathroom
13–18 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.92 out of 5 average rating, 151 reviews
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Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 6 reviews