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Search results; Over 1,000 homes in Chicago

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Guest favourite
Apartment in Chicago
MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Oct
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4.89 out of 5 average rating, 194 reviews
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Home in Forest Park
Ferdinand Front Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Chicago
Sunny Penthouse - Oakwood Beach
2 bedrooms, 3 beds, 2 bathrooms
24–29 Oct
4.95 out of 5 average rating, 76 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
24–29 Oct
4.75 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 7 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, 2 bathrooms
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, 2 bathrooms
25–30 Oct
5.0 out of 5 average rating, 3 reviews
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Superhost
Flat in Chicago
Little Italy 5BR Stay w/ Optional Parking
5 bedrooms, 7 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Apartment in Chicago
3-bedroom exposed brick in Chicago's Wicker Park
3 bedrooms, 4 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 170 reviews
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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
19–24 Oct
4.96 out of 5 average rating, 92 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds, 2 bathrooms
21–26 Oct
5.0 out of 5 average rating, 30 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, 529 reviews
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Top guest favourite
Bungalow in Chicago
Beverly Hills of Chicago Luxury Guest Favorites xx
5 bedrooms, 8 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 33 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Flat in Chicago
Luxury Designer Loft 302 | River North
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
4.8 out of 5 average rating, 15 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
13–18 Dec
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds, 2.5 bathrooms
19–24 Oct
4.97 out of 5 average rating, 69 reviews