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Search results; Over 1,000 homes in Chicago

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Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 beds, 1.5 private bathrooms
26–31 Oct
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4.98 out of 5 average rating, 309 reviews
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Featured hotel
Hotel in Chicago
The Emily Hotel, Deluxe double
1 bedroom, 2 double beds, 1 bathroom
1–6 Oct
4.92 out of 5 average rating, 64 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 36 reviews
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Guest favourite
Flat in Chicago
Luxury Loft Collection 01 - Terrace - River North
3 bedrooms, 8 beds, 3 bathrooms
8–13 Nov
4.9 out of 5 average rating, 126 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, 135 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 double bed, 1 bathroom
5–10 Nov
5.0 out of 5 average rating, 6 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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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds, 1 bathroom
24–29 Oct
4.99 out of 5 average rating, 112 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, 7 reviews
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Top guest favourite
Flat in Chicago
Charming, Spacious 3BR Lakeview Apt Near Transit
3 bedrooms, 3 beds, 1 bathroom
8–13 Nov
4.97 out of 5 average rating, 461 reviews
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Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds, 2 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds, 1 bathroom
1–6 Nov
4.94 out of 5 average rating, 263 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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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.94 out of 5 average rating, 178 reviews
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Top guest favourite
Flat in Chicago
Chic retreat near the best of Lakeview & Wrigley
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 196 reviews
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Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed, 1 bathroom
15–20 Nov
4.92 out of 5 average rating, 545 reviews
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Top guest favourite
Guest house in Chicago
Horner Park Coach House
1 bedroom, 2 beds, 1 bathroom
11–16 Nov
5.0 out of 5 average rating, 14 reviews
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Top guest favourite
Guest house in Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 965 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