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Search results; Over 1,000 homes in Chicago

Featured hotel
Hotel in Chicago Loop
The Royal Sonesta Chicago Downtown, King - city...
1 bedroom, 1 bed, 1 private bathroom
27 Jun – 2 Jul
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4.74 out of 5 average rating, 178 reviews
Top guest favourite
Flat in Chicago Loop
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, 1 queen bed
24–29 Jun
4.97 out of 5 average rating, 64 reviews
Flat in Logan Square
Retro Logan Square Retreat • Blue Line
1 bedroom, 1 bunk bed
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in West Side
Pilsen Modern Chic Retreat
2 bedrooms, 3 beds
2–7 Jul
4.95 out of 5 average rating, 115 reviews
Top guest favourite
Home in Chicago
New Home | O'Hare Airport
4 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Room in Norwood Park
Private Room in Norwood Park
1 bed
28 Jun – 3 Jul
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Flat in Bridgeport
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds
9–14 Aug
4.97 out of 5 average rating, 62 reviews
Guest favourite
Place to stay in South Side
Large Brand New Room in Hyde Park Close toDowntown
1 bedroom, 1 queen bed
14–19 Oct
4.95 out of 5 average rating, 19 reviews
Superhost
Apartment in North Side
Lovely top floor 2BR/2BA, steps from everything!
2 bedrooms, 2 beds
27 Jun – 2 Jul
4.96 out of 5 average rating, 156 reviews
Featured hotel
Hotel in Downtown Chicago
Deluxe king room & rooftop bar with views
1 bedroom, 1 king bed
9–14 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Flat in Wicker Park
DT Wicker Deluxe | Sleeps 6| 2-Car Parking&Laundry
2 bedrooms, 3 beds
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Bridgeport
Blue Brick Apartment in Bridgeport - Park for Free
2 bedrooms, 2 double beds
25–30 Jun
4.96 out of 5 average rating, 101 reviews
Guest favourite
Place to stay in Rogers Park Township
C4. 9 min to Red Line and Lyola University
1 bedroom, 2 beds
21–26 Jun
4.84 out of 5 average rating, 19 reviews
Flat in Downtown Chicago
Luxury South Loop Apt
2 beds
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
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
24–29 Oct
5.0 out of 5 average rating, 40 reviews
Guest favourite
Place to stay in Norwood Park
The Native Garden at the City's Edge
1 bedroom, 1 queen bed
4–9 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Apartment in North Side
Stylish Chicago Firefighter 3 bed Retreat-Sleeps 7
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 75 reviews
Top guest favourite
Flat in South Side
Luxury Living in Bronzeville with Massive Roofdeck
3 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 13 reviews