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Search results; Over 1,000 homes in Chicago

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Guest favourite
Flat in Chicago
River North | Private Balcony With In&Out Parking
2 bedrooms, 2 beds, 1 private bathroom
4–9 Oct
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4.86 out of 5 average rating, 135 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds
1–6 Nov
New place to stay
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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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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds
26–31 Dec
New place to stay
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds
8–13 Nov
New place to stay
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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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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
20–25 Sept
New place to stay
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorite
5 bedrooms, 8 beds
19–24 Sept
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Top guest favourite
Flat in Chicago
Beautiful Home | Great for Groups, Parking & Food
6 bedrooms, 9 beds
8–13 Nov
4.98 out of 5 average rating, 63 reviews
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Top guest favourite
Flat in Berwyn
Cozy, Sunny, and Clean Apt 3 bd Free Parking
3 bedrooms, 3 double beds
20–25 Sept
4.91 out of 5 average rating, 82 reviews
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Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds
5–10 Oct
5.0 out of 5 average rating, 25 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
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
25–30 Oct
5.0 out of 5 average rating, 15 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, 101 reviews
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Guest favourite
Guest suite in Chicago
2 Bedroom Apartment by O'Hare/CTA/I90 Free Parking
2 bedrooms, 3 beds
23–28 Oct
4.88 out of 5 average rating, 447 reviews
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Guest favourite
Room in Forest Park
Cozy City Get-away on Marengo
1 double bed
12–17 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Flat in Chicago
Andersonville Living
3 bedrooms, 5 beds
9–14 Nov
4.94 out of 5 average rating, 499 reviews