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Search results; Over 1,000 homes in Chicago

Guest favourite
Apartment in West Side
The Upscale Getaway Near Downtown
2 bedrooms, 3 beds, 2 private bathrooms
12–17 Aug
,
4.93 out of 5 average rating, 291 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
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 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
Guest favourite
Room in Norwood Park
Private Room in Norwood Park
1 bed, 1 bathroom
28 Jun – 3 Jul
4.97 out of 5 average rating, 38 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
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed, 1 bathroom
14–19 Oct
4.95 out of 5 average rating, 19 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
Flat in Downtown Chicago
Luxury South Loop Apt
2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 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
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
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
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
Guest favourite
Place to stay in Rogers Park Township
C4. 9 min to Red Line and Lyola University
1 bedroom, 2 beds, 2 bathrooms
21–26 Jun
4.84 out of 5 average rating, 19 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
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
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
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Flat in North Side
2BR Avondale Apt: Free Parking + Steps to Blueline
2 bedrooms, 3 beds, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 7 reviews