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Vacation rentals in Chicago

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Top-rated vacation rentals in Chicago

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

Apartment in West Loop
1BR Perfect Home in the City, Close to Everything
Welcome to our stunning 1BR apartment in Chicago West Loop-Fulton area! Perfectly designed for a business trip or vacation, our space boasts all the amenities you need for a comfortable stay. Public parking is located just 2 blocks away from N Clinton St. and W Lake St. You'll find an array of shops, restaurants, cafes, and convenience stores nearby. Plus, our building is located across the train station, and it's just 3-minutes walk to the Clinton Subway. Downtown is also 15 minutes away!
Guest favourite
Loft in Lake View
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.
Apartment in Uptown
Elegant Uptown Studio near Red Line.
Welcome to this beautifully renovated studio apartment located in the Uptown neighborhood. This apartment has access to a shared fitness area, backyard/garden, and comfy work station. The building is a block from the Red Line train and is walking distance to neighborhood restaurants, bars, shops, and cafes. This apartment is perfect for remote workers or travelers looking to be in a nice neighborhood close to the city! Check in is completely contactless with a keypad & door code.

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Other great vacation rentals in Chicago

Apartment in Lake View
Uplifting Studio Apartment in Belmont
Guest favourite
Apartment in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Guest favourite
Apartment in Chicago
Modern Apt with style & comfort in Pilsen Chicago
Guest favourite
Apartment in Near North Side
Great Location Studio in the Gold Coast!!
Apartment in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
Apartment in Magnificent Mile
Charming 1BR Unit Great Location
Apartment in Magnificent Mile
Gold Coast 1BR Hideaway w/ Spacious Living Area
Apartment in Near North Side
One-Bedroom Nicely Decorated Apartment w/ Laundry
Apartment in Logan Square
Lofted 2nd Floor Apartment with Spiral Staircase
Apartment in West Loop
Peaceful & Complete 1BR Home w/ In-Unit Laundry
Guest favourite
Apartment in Near North Side
50th Floor Mag Mile Studio
Apartment in Lake View
Stunning Newly Remodeled Studio Apt in Lakeview

Quick stats about vacation rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K reviews

Destinations to explore

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