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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Ukrainian Village 3BR/3BA • Private Patio, Parking
3 bedrooms, 4 beds, 3 private bathrooms
26–31 Oct
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4.98 out of 5 average rating, 128 reviews
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Guest favourite
Home in Chicago
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds
13–18 Dec
5.0 out of 5 average rating, 5 reviews
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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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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
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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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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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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Superhost
Flat in Chicago
Pilsen Stay | Primary King | Mins to downtown
2 bedrooms, 3 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Chicago
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
7–12 Jan
4.99 out of 5 average rating, 117 reviews
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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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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
2–7 Nov
4.95 out of 5 average rating, 175 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
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Top guest favourite
Flat in Chicago
NW Chicago Garden Apartment
2 bedrooms, 2 beds
3–8 Nov
4.93 out of 5 average rating, 57 reviews
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Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds
13–18 Dec
5.0 out of 5 average rating, 12 reviews
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Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
1–6 Oct
5.0 out of 5 average rating, 64 reviews
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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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Top guest favourite
Flat in Chicago
Urban Chic Apartment by the Magnificent Mile
2 bedrooms, 2 queen beds
8–13 Dec
4.95 out of 5 average rating, 300 reviews
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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