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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Loop
Modern long-term luxury w/ spectacular view!
1 bedroom, 1 bed, 2 private bathrooms
23–28 Sept
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4.96 out of 5 average rating, 50 reviews
Featured hotel
Room in Downtown Chicago
Level studio suite
1 bathroom
21–26 Oct
Room in Downtown Chicago
Steps to the Magnificent Mile + Free Breakfast
2 beds, 1 bathroom
7–12 Sept
4.67 out of 5 average rating, 3 reviews
Room in The Loop
Near Magnificent Mile | Gym. Free Breakfast.
2 queen beds, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jan
4.95 out of 5 average rating, 132 reviews
Featured hotel
Rooms in Downtown Chicago
Junior two bedroom suite
2 bedrooms, 1 bathroom
27 Sept – 2 Oct
Top guest favourite
Apartment in Downtown Chicago
Luxury 4BD Gold Coast Penthouse with Deck & Views
4 bedrooms, 4 beds, 3 bathrooms
1–6 Nov
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Flat in Downtown Chicago
Coach House in Historic Old Town Chicago
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 143 reviews
Top guest favourite
Home in Humboldt Park
Beautifully Renovated Loft-Style Coach House
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 32 reviews
Superhost
Flat in The Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
17–22 Sept
4.86 out of 5 average rating, 149 reviews
Home in Lincoln Park
Charming Historic Row Home | Lincoln Park
3 bedrooms, 3 beds, 2 bathrooms
15–20 Nov
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in West Side
Pilsen Prism: Sun-Drenched 3BR + Parking
3 bedrooms, 3 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Flat in Wicker Park
【Central】- Eclectic Fun 1BR APT in Wicker Park
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 165 reviews
Top guest favourite
Guest house in Little Italy
Polk Street Coach House Apartment, Little Italy/Medical Dist
2 bedrooms, 2 queen beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 961 reviews
Featured hotel
Room in Downtown Chicago
Deluxe king non smoking
1 king bed, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Apartment in West Town
Great location. Free parking.
1 bedroom, 1 queen bed, 1 bathroom
29 Nov – 4 Dec
4.97 out of 5 average rating, 923 reviews
Featured hotel
Hotel in West Loop
Deluxe double
1 bedroom, 2 double beds, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 62 reviews
Guest favourite
Flat in Little Italy
Luxury 5BR/4BA Near Downtown | Free Parking!
5 bedrooms, 7 beds, 3.5 bathrooms
22–27 Oct
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Flat in West Town
ChiCasa Wicker Park Paradise
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Nov
5.0 out of 5 average rating, 62 reviews