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Search results; Over 1,000 homes in Chicago

Top guest favourite
Home in Chicago
The Chicago River House – GIANT wall projector!
2 bedrooms, 2 beds, 2 private bathrooms
20–25 Sept
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4.96 out of 5 average rating, 206 reviews
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.92 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
Top guest favourite
Rooms in Chicago
Historic North Park home
4.97 out of 5 average rating, 117 reviews, 3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
4.93 out of 5 average rating, 107 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
New place to stay, 4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
4.95 out of 5 average rating, 84 reviews, 2 bedrooms, 2 beds, 2 bathrooms
9–14 Aug
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
4.9 out of 5 average rating, 49 reviews, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Nov
Flat in Logan Square
Duplex in Bucktown
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
21–26 Aug
Top guest favourite
Home in Chicago
Big house in the BEST Location!
4.98 out of 5 average rating, 62 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
27 Sept – 2 Oct
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
5.0 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
4.94 out of 5 average rating, 252 reviews, 2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 126 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Dec
Top guest favourite
Room in Roscoe Village
Spacious garden level suite
4.96 out of 5 average rating, 317 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Guest favourite
Guest suite in Logan Square
2BR/1.5 Bath in Logan Square
4.95 out of 5 average rating, 59 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
28 Nov – 3 Dec
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
4.99 out of 5 average rating, 108 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Nov
Flat in South Side
Apartment near McCormick w/ gym & workspace
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Aug
Top guest favourite
Guest house in West Side
Pilsen Gem Near the Loop & Chinatown
5.0 out of 5 average rating, 20 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Sept
Top guest favourite
Flat in Lake View
An elegant Chicago Northside Getaway
5.0 out of 5 average rating, 374 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug