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Search results; Over 1,000 homes in Chicago

Top guest favourite
Apartment in Chicago
Large Remodeled Home in Lincoln Park, Sleeps 12!
4 bedrooms, 5 beds, 3 private bathrooms
19–24 Jul
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4.97 out of 5 average rating, 135 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
Flat in Chicago
Chicago Classic•Skyline View•1BR + Den, Train Near
1 bedroom, 5 beds, 1 bathroom
28 Jun – 3 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Apartment in Chicago
Your Chicago Retreat
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Jun – 3 Jul
4.99 out of 5 average rating, 299 reviews
Superhost
Flat in Clarendon Hills
Clarendon Hills Apartment
2 bedrooms, 2 beds, 1.5 bathrooms
28 Jun – 3 Jul
New place to stay
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, 4 reviews
Guest favourite
Rooms in Chicago
Spacious Haven in North Park
3 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.9 out of 5 average rating, 61 reviews
Top guest favourite
Guest house in Chicago
Cozy Coach House
1 queen bed, 1 bathroom
9–14 Aug
4.96 out of 5 average rating, 496 reviews
Top guest favourite
Room in Chicago
Fresh and Sunny Bed & Bath by UofC
1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.91 out of 5 average rating, 255 reviews
Superhost
Flat in Chicago
Well Located Studio on the Red Line
1 queen bed, 1 bathroom
5–10 Jul
New place to stay
Top guest favourite
Flat in Chicago
Designer Garden Unit in Bridgeport
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Oak Park
Restful Retreat Perfectly Located by Train+Shops
3 bedrooms, 5 beds, 2 bathrooms
29 Aug – 3 Sept
4.9 out of 5 average rating, 495 reviews
Top guest favourite
Flat in Chicago
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 258 reviews
Superhost
Flat in Chicago
Corporate Smart Home At River Walk
1 bedroom, 1 queen bed, 1 bathroom
8–13 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Room in Chicago
Cozy Clean Large Private Room in Lincoln Square
1 double bed, 1 bathroom
22–27 Aug
4.95 out of 5 average rating, 178 reviews
Top guest favourite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 422 reviews
Top guest favourite
Place to stay in Chicago
Spacious Sun-Lit Suite in Chicago
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 16 reviews
Place to stay in Chicago
Private Room for 3 Guests By Grand Ave Blueline
1 bedroom, 2 beds, 2 bathrooms
4–9 Jul
Top guest favourite
Flat in Oak Park
Serene 1-Bedroom Suite in Oak Park (Free Parking!)
1 bedroom, 1 king bed, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 51 reviews