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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in Chicago
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
16–21 Aug
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4.97 out of 5 average rating, 38 reviews
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 129 reviews
Room in Chicago
Iconic Journey | Navy Pier. Free Breakfast*
2 beds, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Shipping container in Evanston
Container home. Walk to NWU and Central Street.
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Chicago
Stylish Hyde Park/Kenwood Brownstone Garden Apt
2 bedrooms, 3 beds, 1.5 bathrooms
16–21 Aug
5.0 out of 5 average rating, 26 reviews
Room in Chicago
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
15–20 Aug
New place to stay
Room in Forest Park
City Get-away on Marengo
1 bed, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Room in Chicago
Guest room in Dunning, Chicago IL
1 queen bed, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Chicago
Kasa Lake Shore Chicago | Two Bedroom King & Queen
2 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
4.87 out of 5 average rating, 15 reviews
Guest favourite
Room in Chicago
near festivals & united center
1 bed, 1 bathroom
30 Aug – 4 Sept
4.95 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Chicago
Explore Lincoln Park from a Polished Apartment
1 bedroom, 1 queen bed, 1 bathroom
30 Nov – 5 Dec
5.0 out of 5 average rating, 319 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 22 reviews
Guest favourite
Guest house in Villa Park
Eclectic Coach House Apartment
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 163 reviews
Flat in Oak Park
Premier Luxe Retreat | Free Parking
1 bedroom, 4 beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Flat in Chicago
The Picasso: #1 Chicago Location
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 56 reviews
Top guest favourite
Flat in Forest Park
Cheerful Remodel Prime Location
1 bedroom, 1 queen bed, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 150 reviews
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 70 reviews
Guest favourite
Flat in Chicago
Quiet & Modern Avondale Apartment
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 17 reviews
Guest favourite
Camper van/Motorhome in Lombard
Couples camper on a quaint horse ranch
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 11 reviews