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Search results; Over 1,000 homes in Chicago

Superhost
Flat in Chicago
2-Story Penthouse Views, Fireplace, Pool, Gym
2 bedrooms, 4 beds, 3 private bathrooms
17–22 Aug
,
4.9 out of 5 average rating, 42 reviews
Guest favourite
Home in Chicago
Luxury 4BR w/ Spa Tub Near UChicago & Obama Center
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.93 out of 5 average rating, 27 reviews
Guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Dec
4.95 out of 5 average rating, 126 reviews
Home in Chicago
Luxury Home | 7 miles to Downtown Chicago | 5 Beds
4 bedrooms, 6 beds, 3.5 bathrooms
8–13 Aug
New place to stay
Room in Chicago
Bridgeport Chicago near everything affordable.
1 single bed, 1 bathroom
16–21 Aug
New place to stay
Guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
4.94 out of 5 average rating, 108 reviews
Home in Chicago
House in Chicago
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
New place to stay
Top guest favourite
Flat in Chicago
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Aug
5.0 out of 5 average rating, 11 reviews
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, 5 reviews
Superhost
Flat in Oak Park
3BR/1BA With Private Garage, Near Train & Shops
3 bedrooms, 3 queen beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chicago
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 56 reviews
Top guest favourite
Room in Des Plains
Near O'Hare | King Bed+Shared Bathroom+Parking
1 king bed, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 10 reviews
Rooms in Berwyn
3Car parking Bungalow/sleeps 8 w/2.5 bath
4 bedrooms, 6 beds, 1 bathroom
14–19 Aug
New place to stay
Top guest favourite
Room in Chicago
Spacious & serene in hip spot. Sleeps 4.
1 queen bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 525 reviews
Guest favourite
Flat in Chicago
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Chicago
Luxury Loft Collection COMBO 01/03 | Terrace
6 bedrooms, 15 beds, 6 bathrooms
1–6 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Flat in Chicago
Great place in the Heart of Pilsen
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Aug
4.96 out of 5 average rating, 27 reviews
Top 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, 22 reviews
Luxe
Flat in Chicago
Luxury Downtown 4BR | Exclusive Design PH
4 bedrooms, 5 beds, 3.5 bathrooms
16–21 Aug
4.98 out of 5 average rating, 41 reviews