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Search results; Over 1,000 homes in Chicago

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Guest favourite
Guest suite in Chicago
Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
3 bedrooms, 4 beds, 1 private bathroom
2–7 Nov
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4.94 out of 5 average rating, 201 reviews
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Top guest favourite
Home in Chicago
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds
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
8–13 Nov
4.9 out of 5 average rating, 126 reviews
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Guest favourite
Home in Chicago
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
18–23 Jan
4.95 out of 5 average rating, 318 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, 135 reviews
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Guest favourite
Room in Chicago
Charming Room in Historic Ukrainian Village!
1 queen bed
30 Nov – 5 Dec
5.0 out of 5 average rating, 8 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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Top guest favourite
Flat in Chicago
Luxury Penthouse Collection PH4 - Fulton Market
3 bedrooms, 7 beds
1–6 Nov
5.0 out of 5 average rating, 7 reviews
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Guest favourite
Flat in Chicago
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
1–6 Nov
4.94 out of 5 average rating, 263 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
6–11 Dec
4.99 out of 5 average rating, 965 reviews
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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, 501 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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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, 62 reviews
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Top guest favourite
Flat in Chicago
European Coziness in Bronzeville
3 bedrooms, 4 beds
30 Oct – 4 Nov
5.0 out of 5 average rating, 12 reviews
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Superhost
Flat in Chicago
West Loop Loft|Sleeps 4, Parking, Pool, & Rooftops
1 bedroom, 3 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest suite in Chicago
Cozy, Quiet, Garden Getaway!
1 bedroom, 1 queen bed
15–20 Nov
4.92 out of 5 average rating, 545 reviews
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Top guest favourite
Guest suite in Chicago
Eddy Street Upstairs Apartment
1 bedroom, 1 bed
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
1–6 Nov
4.93 out of 5 average rating, 196 reviews
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Top guest favourite
Guest suite in Oak Park
Entire upstairs in Arts and Crafts Oak Park home
2 bedrooms, 3 beds
12–17 Oct
4.91 out of 5 average rating, 543 reviews