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Search results; Over 1,000 homes in Chicago

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Apartment in Chicago
Modern Luxury In Old Town - Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
17–22 Oct
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4.76 out of 5 average rating, 279 reviews
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Guest favourite
Room in Chicago
Quaint Cozy Vintage for two in Lincoln Park
1 queen bed, 1 bathroom
9–14 Nov
4.9 out of 5 average rating, 68 reviews
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Flat in Chicago
Luxury penthouse with city views
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Flat in Chicago
Avondale Creative Loft | King Bed•Games•Parking
2 bedrooms, 2 beds, 1 bathroom
15–20 Nov
4.98 out of 5 average rating, 44 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
1–6 Nov
4.9 out of 5 average rating, 126 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed, 1 bathroom
1–6 Dec
4.94 out of 5 average rating, 448 reviews
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Top guest favourite
Flat in Chicago
A Whimsical Fairy-tale Loft in Ravenswood Chicago
2 bedrooms, 3 beds, 1 bathroom
26–31 Oct
4.99 out of 5 average rating, 364 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
27 Sept – 2 Oct
New place to stay
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Top guest favourite
Flat in Chicago
A Stylish, sundrenched Chicago Ravenswood Flat
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 363 reviews
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Guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
15–20 Nov
4.97 out of 5 average rating, 75 reviews
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Guest favourite
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
4.95 out of 5 average rating, 175 reviews
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Top guest favourite
Flat in Chicago
Little Italy Historic Restoration Row House
2 bedrooms, 2 queen beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 61 reviews
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Top guest favourite
Flat in Chicago
Bright Cozy Modern-Chic Condo in Trendy West Town
1 bedroom, 2 queen beds, 1 bathroom
3–8 Jan
4.98 out of 5 average rating, 258 reviews
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Top guest favourite
Flat in Forest Park
Sunny 1 bedroom apartment 1 block from restaurants
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 229 reviews
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Top guest favourite
Flat in Chicago
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 324 reviews
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Top guest favourite
Guest suite in Chicago
Logan Square Chicago 2BR cottage, close to it all!
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.87 out of 5 average rating, 130 reviews
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Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Nov
4.92 out of 5 average rating, 544 reviews
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Guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews