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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.

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.

  • Experience Millennium Park on a Chicago Vacation

    Millennium Park

    Public green space with art and ice rink

  • Enjoy the view from the Willis Tower during your Chicago vacation

    Willis Tower

    Tallest skyscraper in Chicago with observation deck

  • 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

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