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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Steps away from Wrigley Field!!
2 bedrooms, 2 beds, 1 private bathroom
17–22 Sept
,
4.99 out of 5 average rating, 127 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Chicago
Vintage library museum retreat near CTA brown line
2 bedrooms, 2 beds
27 Jan – 1 Feb
5.0 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
4–9 Aug
4.94 out of 5 average rating, 108 reviews
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed
16–21 Aug
New place to stay
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
Flat in Chicago
Duplex in Bucktown
3 bedrooms, 3 beds
21–26 Aug
New place to stay
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed
19–24 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds
15–20 Aug
5.0 out of 5 average rating, 11 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds
9–14 Aug
New place to stay
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Chicago
Room w/ Private Bath | Chicago IL
1 queen bed
9–14 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 queen beds
22–27 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Chicago
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
Guest favourite
Home in Villa Park
Cozy 5BD Home with Scandinavian Vibes
5 bedrooms, 5 beds
8–13 Aug
4.9 out of 5 average rating, 42 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds
8–13 Aug
New place to stay
Top guest favourite
Flat in Chicago
Cozy & Spacious Sunny 2 bedroom apartment.
2 bedrooms, 2 beds
19–24 Oct
4.98 out of 5 average rating, 108 reviews