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Search results; Over 1,000 homes in Chicago

Top guest favourite
Flat in West Loop
Gym, Garage Parking, Balcony, Sleeps 4
2 bedrooms, 2 beds, 2 private bathrooms
14–19 Aug
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5.0 out of 5 average rating, 34 reviews
Top guest favourite
Flat in Chicago Loop
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 West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Oct
4.95 out of 5 average rating, 115 reviews
Flat in Logan Square
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
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
Home in South Side
The Dorchester | Steps to the Obama Center & Beach
5 bedrooms, 10 beds, 3.5 bathrooms
27 Jun – 2 Jul
New place to stay
Top guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds, 1 bathroom
25–30 Jun
4.96 out of 5 average rating, 101 reviews
Guest favourite
Place to stay in Norwood Park
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
Guest favourite
Apartment in South Side
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
Flat in Uptown
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
Superhost
Apartment in North Side
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 Wicker Park
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
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
Top guest favourite
Guest house in West Side
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
Top guest favourite
Flat in West Town
Boho City Escape | Parking + Balcony
2 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Apartment in Wrigleyville
Wrigleyville Inn. Historic Greystone, Free Parking
3 bedrooms, 3 queen beds, 2 bathrooms
4–9 Oct
4.99 out of 5 average rating, 114 reviews
Top guest favourite
Apartment in North Side
Stylish Chicago Firefighter 3 bed Retreat-Sleeps 7
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.97 out of 5 average rating, 75 reviews
Flat in Downtown Chicago
Luxury South Loop Apt
2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Place to stay in Chicago
On The Go Travelers 1 Private Bdrm & BR
1 bedroom, 1 bed, 1 bathroom
29 Jun – 4 Jul
5.0 out of 5 average rating, 3 reviews