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Search results; Over 1,000 homes in Chicago

Top guest favourite
Guest house in Chicago
Charming private coach house
1 bedroom, 2 beds, 1 private bathroom
23–28 Sept
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4.97 out of 5 average rating, 60 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4.95 out of 5 average rating, 22 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
16–21 Aug
Place to stay in Chicago
Guest room in Dunning, Chicago IL
New place to stay, 1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
Home in Franklin Park
Full, fun cozy house!
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 4 beds, 1 bathroom
8–13 Aug
Top guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
5.0 out of 5 average rating, 8 reviews, 2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
Superhost
Place to stay in Chicago
Woodlawn Beauty: Room 2
4.5 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Luxury Living in Bronzeville with Massive Roofdeck
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 3 beds, 2 bathrooms
30 Aug – 4 Sept
Guest favourite
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
5.0 out of 5 average rating, 9 reviews, 2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
4.95 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
12–17 Oct
Guest favourite
Guest suite in Chicago
Exemplary Wicker Park Manor Two Bed Guest Suite
5.0 out of 5 average rating, 19 reviews, 2 bedrooms, 2 beds, 2 bathrooms
19–24 Aug
Top guest favourite
Room in Chicago
Spacious garden level suite
4.96 out of 5 average rating, 313 reviews, 1 queen bed, 1 bathroom
10–15 Nov
Top guest favourite
Home in Chicago
Boho Luxe Retreat | Garage Parking | Sleeps 13
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Flat in Chicago
Modern 2 BR Retreat Steps From Family Park
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
4.98 out of 5 average rating, 87 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Place to stay in Chicago
x3 Private room with bath Hyde Park UChicago
5.0 out of 5 average rating, 14 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Guest favourite
Flat in Chicago
Luxury Designer Apartment 803| Gold Coast/Old Town
4.95 out of 5 average rating, 19 reviews, 2 bedrooms, 2 bathrooms
16–21 Aug
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept