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Experience a unique view of the skyline on a Chicago vacation

Chicago Vacations

The top sights, highlights, tours & travel itinaries curated by our Travel Experts.

    Plan your Trip
    1. Destinations
    2. North America
    3. USA
    4. Chicago

    Our expert tips for your Chicago vacation

    Chicago is a diverse mega-metropolis where exciting architecture with breathtaking views meets a diverse gastro and cultural scene. The so-called Windy City is the third largest city in the USA and is located in the state of Illinois on Lake Michigan. Explore Millennium Park with its world-famous sculpture "the bean" and enjoy top-notch drinks and live music at a jazz club. With Tourlane, you can book your flights, transfers, accommodations and guides - all in one place! Our travel experts will create your perfect tour package according to your travel tastes and preferences.

    1. Experience Millennium Park on a Chicago Vacation

      Millennium Park

      Public green space with art and ice rink

    2. Enjoy the view from the Willis Tower during your Chicago vacation

      Willis Tower

      Tallest skyscraper in Chicago with observation deck

    3. Experience Navy Pier on a Chicago Vacation

      Navy Pier

      pier with rides, shops and restaurants

    What to See During Your Chicago Vacation?

    1. Millennium Park

    Millennium Park is one of the top sights in Chicago. Originally planned at the turn of the millennium, the public green space was opened in July 2004. Millennium Park is located directly on Lake Michigan and invites you to take a walk in the warm season and ice skating in the winter. Besides numerous restaurants, there are works of famous architects to admire. The most famous sculpture is Cloud Gate, nicknamed "the bean" because of its shape.

    2. Willis Tower

    The Willis Tower is the tallest building in Chicago. Elevators take visitors to the 103rd floor visitor platform, which is 1,350 feet above the ground. From here you can enjoy a phenomenal view. On a clear day you can see up to 50 miles away.

    3. Navy Pier

    The Navy Pier juts out into Lake Michigan about a kilometer away. Built in 1916, the pier is one of the city's entertainment centers. Numerous rides, playgrounds, shops and restaurants are located on Navy Pier.

    4. Art Institute of Chicago

    One of Chicago's more than 60 museums is the Art Institute of Chicago. Founded in 1866, the art museum offers a permanent collection of 300,000 works from different eras. The Art Institute of Chicago is particularly famous for its collection of famous Impressionists and Post-Impressionists. Major works by artists such as Vincent Van Gogh and Claude Monet are on display here.

    5. The Magnificent Mile

    The Magnificent Mile is a shopping and strolling street. The boulevard is lined with exclusive shops, museums and high-end restaurants. A stroll down the Magnificent Mile is especially delightful in winter, when the street is ablaze with thousands of twinkling lights. Less

    Other Places to Visit During Your Tour

    1. Blick auf die Küstenstadt bei einem Myrtle Beach Urlaub in South Carolina mit Tourlane

      Myrtle Beach

    2. See wild bison during your Yellowstone Vacation, pictured here crossing the road, as part of a tour of North America.

      Yellowstone

    3. Erleben Sie eine Welt des Glamours bei einer Hollywood Tour mit Tourlane.

      Hollywood

    4. Mann wandert entlang des Colorado River durch den Grand Canyon in Arizona USA

      Grand Canyon

    5. Plan a Route 66 Tour during your trip in the American West in the USA.

      Route 66

    6. Erleben Sie bei einer Kings Canyon Tour ein beeindruckendes Naturwunder in den USA.

      Kings Canyon

    7. Discover the Downtown district during your Phoenix vacation.

      Phoenix

    8. Experience the city's coastline on your Honolulu vacation

      Honolulu

    9. Experience colorful houses on a New Orleans vacation

      New Orleans

    10. View of the Orlando skyline - to experience on an Orlando vacation

      Orlando

    11. Experience a unique view of the skyline on your Miami vacation

      Miami

    12. View of the landmark of San Francisco: The Golden Gate Bridge in the USA

      San Francisco

    13. Take in the skyline on a city break to New York

      New York

    14. View_of_the_Griffith_Park_Observatory_with_the_Skyline_of_Los_Angeles_in_the_background

      Los Angeles

    15. The_Las_Vegas_trip_at_Night_viewed_from_the_air_with_colorfully_lit_Casinos

      Las Vegas

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