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Holiday rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Flat in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.
Superhost
Loft in Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.
Superhost
Home in Chicago
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
Professional Host

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
Wrigley Field1,004 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Magnificent Mile597 locals recommend

Other great holiday rentals in Chicago

Superhost
Apartment in Chicago
Unique Lincoln Park Duplex Apt
Individual Host
Superhost
Flat in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
Individual Host
Superhost
Flat in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
Superhost
Flat in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
Individual Host
Superhost
Apartment in Chicago
Great location. Free parking.
Individual Host
Superhost
Flat in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
Superhost
Flat in Chicago
Explore the City from an Elegant, Urban Retreat
Professional Host
Superhost
Flat in West Town
Ukrainian Village Garden Retreat
Professional Host
Superhost
Flat in Lincoln Park
Sophisticated Flat in Historic Building
Individual Host
Superhost
Flat in Oak Park
Cosmopolitan Nest in Oak Park North Side
Individual Host
Superhost
Flat in Chicago
Lovely Andersonville Apt with Ideal Location
Individual Host
Superhost
Guest house in Chicago
Entire private coach house near transit, nightlife
Individual Host

Destinations to explore

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  2. United States
  3. Illinois
  4. Cook County
  5. Chicago