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Search results; Over 1,000 homes in Chicago

Guest favourite
Home in Chicago
Beautiful Chicago Greystone
4 bedrooms, 4 beds, 1 private bathroom
7–12 Sept
,
4.93 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Chicago
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed, 1 bathroom
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Flat in Chicago
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 115 reviews
Top guest favourite
Room in Chicago
Cozy Room for One In The Company of Cats -Blueline
1 single bed, 1 bathroom
1–6 Jul
4.94 out of 5 average rating, 139 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Flat in Chicago
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Place to stay in Chicago
The Native Garden at the City's Edge
1 bedroom, 1 queen bed, 1 bathroom
4–9 Aug
5.0 out of 5 average rating, 6 reviews
Featured hotel
Hotel in Chicago
Deluxe king room & rooftop bar with views
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Lockport
Bright Lockport Farmhouse: King Bed + Yard View
1 bedroom, 1 bed, 1 bathroom
20–25 Jun
4.98 out of 5 average rating, 43 reviews
Flat in Chicago
Bright 1BR unit w/ elevator & Wifi
1 bedroom, 1 queen bed, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Guest house in Chicago
Pilsen Gem Near the Loop & Chinatown
1 bedroom, 2 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Flat in Chicago
Chicago Addison St. 1 bed/1 bath condo, Garden Lvl
1 bedroom, 1 bed, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Apartment in Chicago
The Modern Woodlawn 2 Bed 2 Bath
2 bedrooms, 2 beds, 2 bathrooms
16–21 Aug
4.96 out of 5 average rating, 79 reviews
Superhost
Apartment in Chicago
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds, 2 bathrooms
27 Jun – 2 Jul
4.96 out of 5 average rating, 156 reviews
Superhost
Flat in Chicago
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Flat in Chicago
Luxury South Loop Apt
2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Flat in Chicago
Lake Shore Condo | Beach | North Chicago
2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Flat in Chicago
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 15 reviews
Home in Chicago
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms, 10 beds, 3.5 bathrooms
27 Jun – 2 Jul
New place to stay