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Search results; Over 1,000 homes in Chicago

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Superhost
Flat in Chicago
North Side Pied-à-terre
2 bedrooms, 2 beds, 1 private bathroom
3–8 Oct
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4.76 out of 5 average rating, 303 reviews
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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
15–20 Nov
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
21–26 Oct
5.0 out of 5 average rating, 57 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
18–23 Jan
4.95 out of 5 average rating, 131 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds
7–12 Sept
4.96 out of 5 average rating, 45 reviews
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Top guest favourite
Home in Chicago
Spacious Retro Logan Square Loft
4 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
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Top guest favourite
Flat in Oak Park
Curated & Spacious Duplex Near Downtown w/Parking
3 bedrooms, 5 beds
11–16 Nov
5.0 out of 5 average rating, 96 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
1–6 Nov
5.0 out of 5 average rating, 27 reviews
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Room in Chicago
Iconic City | Riverwalk. Free Breakfast*
2 beds
20–25 Sept
New place to stay
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Guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds
30 Sept – 5 Oct
4.98 out of 5 average rating, 188 reviews
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Top guest favourite
Flat in Chicago
Fully Furnished Apartment Wicker Park Free Parking
1 bedroom, 1 queen bed
9–14 Nov
4.97 out of 5 average rating, 630 reviews
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Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
20–25 Sept
4.92 out of 5 average rating, 38 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, 520 reviews
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Guest favourite
Apartment in Chicago
Condo off the lake
3 bedrooms, 3 queen beds
22–27 Oct
4.88 out of 5 average rating, 78 reviews
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Top guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds
25–30 Oct
4.96 out of 5 average rating, 136 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 28 reviews