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Search results; Over 1,000 homes in Chicago

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Superhost
Apartment in Chicago
Spacious 4 Bedroom Condo
4 bedrooms, 4 beds, 3.5 private bathrooms
25–30 Oct
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4.95 out of 5 average rating, 218 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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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, 35 reviews
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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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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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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds
2–7 Nov
4.94 out of 5 average rating, 500 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
27 Sept – 2 Oct
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, 103 reviews
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Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom Double Queen
2 bedrooms, 3 beds
21–26 Sept
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.95 out of 5 average rating, 76 reviews
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Top guest favourite
Apartment in Chicago
Lincoln Square Gem!
2 bedrooms, 2 queen beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 509 reviews
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Guest favourite
Flat in Chicago
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
18–23 Oct
4.93 out of 5 average rating, 249 reviews
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 363 reviews
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Home in Wood Dale
Entire 3B/2B Home in Wood Dale-Near O'Hare Airport
3 bedrooms, 3 beds
4–9 Oct
New place to stay
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Top guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds
12–17 Oct
4.91 out of 5 average rating, 542 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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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 110 reviews