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Search results; Over 1,000 homes in Chicago

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Superhost
Flat in Chicago
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
2 bedrooms, 2 beds, 2 private bathrooms
18–23 Oct
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4.77 out of 5 average rating, 230 reviews
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Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
New place to stay
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 130 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, 12 reviews
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Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 38 reviews
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Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Sept
4.88 out of 5 average rating, 145 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 18 beds, 3.5 bathrooms
7–12 Sept
4.95 out of 5 average rating, 44 reviews
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Room in Forest Park
Cozy City Get-away on Marengo
1 double bed, 1 bathroom
28 Sept – 3 Oct
New place to stay
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 27 reviews
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Superhost
Flat in Chicago
Modern Duplex · 3BR/2BA · Sleeps 8 · Free Parking
3 bedrooms, 4 beds, 2 bathrooms
26 Sept – 1 Oct
5.0 out of 5 average rating, 21 reviews
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Flat in Chicago
A 2 BR Bronzeville Getaway
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Sept
New place to stay
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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, 73 reviews
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Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
New place to stay
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Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 244 reviews
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
7–12 Nov
4.9 out of 5 average rating, 519 reviews
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Top guest favourite
Flat in Chicago
Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!
5 bedrooms, 6 beds, 3 bathrooms
7–12 Sept
4.94 out of 5 average rating, 580 reviews
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Guest favourite
Home in Chicago
The Full House
4 bedrooms, 10 beds, 3.5 bathrooms
25–30 Oct
4.96 out of 5 average rating, 135 reviews