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Search results; Over 1,000 homes in Chicago

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Guest favourite
Home in Chicago
The Roscoe House near Wrigley Field
3 bedrooms, 4 beds, 3 private bathrooms
13–18 Oct
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4.94 out of 5 average rating, 407 reviews
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Home in Forest Park
Ferdinand Rear Home
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Jan
4.75 out of 5 average rating, 4 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
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
24–29 Jan
4.95 out of 5 average rating, 136 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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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, 4 reviews
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Flat in Chicago
New 3BR 2 bath family home - 10 min from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 4 reviews
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Superhost
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 151 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, 1 bathroom
23–28 Oct
4.88 out of 5 average rating, 450 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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Guest favourite
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, 5 reviews
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Top guest favourite
Flat in Chicago
3BR/2BA · Sleeps 8 · Free Parking · Soldier Field
3 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
5.0 out of 5 average rating, 26 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, 93 reviews
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Top guest favourite
Flat in Chicago
Bronzeville Hidden Oasis
4 bedrooms, 6 beds, 2 bathrooms
10–15 Nov
4.98 out of 5 average rating, 189 reviews
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Flat in Chicago
Big 2BR Apt 4 mins to West Loop
2 bedrooms, 2 queen beds, No bathroom
1–6 Nov
New place to stay
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Guest favourite
Home in Chicago
Explore Chicago • Private Parking • Museum Access
2 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 32 reviews
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Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Chicago
Chicago Home (1st floor) by Midway near Downtown
3 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.95 out of 5 average rating, 111 reviews
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Guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds, 1 bathroom
11–16 Nov
4.93 out of 5 average rating, 58 reviews