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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
4 bedrooms, 4 beds, 3 private bathrooms
24–29 Oct
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5.0 out of 5 average rating, 25 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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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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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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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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Flat in Chicago
Stylish Chicago Home | 3BR Near Downtown
3 bedrooms, 3 beds
7–12 Sept
New place to stay
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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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Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
30 Sept – 5 Oct
5.0 out of 5 average rating, 3 reviews
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Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 60 reviews
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Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 8 reviews
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Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 26 reviews
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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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Top guest favourite
Home in Chicago
Home in Bucktown | Park for Free | Walk to Train
5 bedrooms, 5 king beds
24–29 Sept
4.94 out of 5 average rating, 16 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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Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 7 reviews
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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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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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Flat in Chicago
Comfortable Vintage North Side Retreat for 8
3 bedrooms, 5 beds
29 Sept – 4 Oct
4.92 out of 5 average rating, 258 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