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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Lincoln Park
Unique Lincoln Park Duplex Apt
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.96 out of 5 average rating, 546 reviews
Guest favourite
Home in South Side
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
4–9 Oct
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Rooms in Chicago
Historic North Park home
3 bedrooms, 4 beds
20–25 Sept
4.97 out of 5 average rating, 117 reviews
Guest favourite
Apartment in South Side
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds
9–14 Aug
4.95 out of 5 average rating, 84 reviews
Home in Belmont Cragin
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Guest favourite
Room in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bed
24–29 Oct
4.9 out of 5 average rating, 49 reviews
Top guest favourite
Home in Bridgeport
Peaceful Modern Full House in Trendy Bridgeport
2 bedrooms, 2 queen beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 305 reviews
Top guest favourite
Home in Chicago
Big house in the BEST Location!
3 bedrooms, 3 beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Room in Roscoe Village
Spacious garden level suite
1 queen bed
10–15 Nov
4.96 out of 5 average rating, 317 reviews
Guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
2–7 Aug
4.95 out of 5 average rating, 104 reviews
Home in Chicago
Modern 3BR Stay w Parking, Near Museums & Downtown
3 bedrooms, 4 beds
23–28 Aug
New place to stay
Top guest favourite
Flat in Ukrainian Village
Designer CuratedVintage Condo in Popular West Town
2 bedrooms, 3 beds
25–30 Oct
4.94 out of 5 average rating, 252 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 4 beds
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Flat in Logan Square
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Flat in Edgewater
Modern 1 BR Near the L, Beach - Bright and Sunny!
1 bedroom, 2 beds
2–7 Nov
5.0 out of 5 average rating, 15 reviews
Guest favourite
Flat in South Side
Modern Soul Retreat: 3BR in Bronzeville/HydePark
3 bedrooms, 3 queen beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in West Rogers Park
Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
1 bedroom, 2 beds
3–8 Dec
4.99 out of 5 average rating, 108 reviews
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
25–30 Oct
4.95 out of 5 average rating, 126 reviews
Guest favourite
Home in Lincoln Park
Charming 3-BED in Lincoln Park/ Old Town & Parking
3 bedrooms, 3 beds
4–9 Oct
4.95 out of 5 average rating, 187 reviews