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Search results; Over 1,000 homes in Chicago

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Guest favourite
Guest suite in Chicago
Cozy and Private Andersonville Retro Studio
Studio, 1 bed, 1 private bathroom
9–14 Nov
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4.87 out of 5 average rating, 416 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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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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Top guest favourite
Flat in Chicago
Paradise on the Boulevard!
2 bedrooms, 3 beds
24–29 Oct
4.99 out of 5 average rating, 111 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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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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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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Top guest favourite
Room in Oak Park
Antique Filled Home
1 bed
1–6 Dec
4.94 out of 5 average rating, 448 reviews
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Top guest favourite
Home in Chicago
2BD/1 BA with summer patio in quiet Roscoe Village
2 bedrooms, 2 beds
16–21 Nov
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed
25–30 Oct
4.96 out of 5 average rating, 515 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 Chicago
Gorgeous, cozy 1-bedroom Suite in Andersonville
1 bedroom, 1 queen bed
15–20 Nov
4.96 out of 5 average rating, 417 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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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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Flat in Chicago
Cozy Chicago Studio | Washer, Near Transit & Eat
1 queen bed
24–29 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Room in Chicago
Spacious garden level suite
1 queen bed
29 Nov – 4 Dec
4.96 out of 5 average rating, 327 reviews
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Top guest favourite
Flat in Chicago
Spacious Studio w/Balcony in Bucktown/Wicker Park
2 beds
23–28 Oct
4.95 out of 5 average rating, 189 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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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