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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Flat in Chicago
Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach
3 bedrooms, 3 beds, 2 private bathrooms
25–30 Oct
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4.95 out of 5 average rating, 128 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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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
25–30 Oct
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
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
24–29 Oct
4.75 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Chicago
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
21–26 Oct
5.0 out of 5 average rating, 30 reviews
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Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
19–24 Oct
4.96 out of 5 average rating, 93 reviews
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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
25–30 Oct
5.0 out of 5 average rating, 7 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, 450 reviews
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Top guest favourite
Apartment in Chicago
Luxe Loft vibe | King Suite |4BR 3Ba
4 bedrooms, 4 beds
24–29 Oct
5.0 out of 5 average rating, 26 reviews
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Top guest favourite
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
18–23 Oct
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
24–29 Jan
4.95 out of 5 average rating, 133 reviews
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Guest favourite
Flat in Chicago
Modern 6BR Suite with Pool-table near McCormick
6 bedrooms, 6 king beds
1–6 Nov
4.9 out of 5 average rating, 42 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds
4–9 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
25–30 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Berwyn
Essential Berwyn Bungalow
3 bedrooms, 4 beds
1–6 Oct
New place to stay
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Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds
2–7 Nov
5.0 out of 5 average rating, 33 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, 58 reviews