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Navy Pier, built in 1916, was the largest in the world at that time. It served as a docking area for passenger excursion steamers and cargo ships. During both World Wars, Navy Pier was utilized for military purposes such as housing, training, and more. In its non-military role, the pier had many attractions, including a streetcar line, theater, emergency room, picnicking areas, dance hall, auditorium, children's playground, and more. Navy Pier, which sits on the lakefront, occupies approximately 50 acres of land, with sprawling parks, gardens, and sculptures on the lawns. The attraction also has several shops and restaurants. Navy Pier offers a variety of activities, including boat parades, air shows, sightseeing tours, festivals, and fireworks, making it the most popular tourist attraction in Chicago.

Lollapalooza is a music festival that features over 170 bands across nine stages worldwide. The festival takes place in Grant Park, located in the heart of downtown Chicago, with the stunning Chicago skyline serving as a backdrop. In addition to the impressive lineup, Lolla offers interactive areas where attendees can participate in giveaways, purchase merchandise, and more. Chow Town, the festival's food area, features delicious food, drinks, and sweets from some of Chicago's favorite restaurants. The emphasis is on fresh, reasonably priced items from local vendors rather than the typical "carnival" fare. For those looking to elevate their Lolla experience, you can purchase GA+, VIP, or Platinum tickets, which provide access to prime views, exclusive lounges, luxury amenities, and getaways from the crowds.

The Marriott Theatre in Lincolnshire is a popular entertainment venue that has thrilled over seven million people with its award-winning productions of Broadway musicals. Some of the audience favorites include "Cats," "Beauty and the Beast," "Fiddler on the Roof," "Les Miserables," and "Hairspray." The theater, founded in 1975, is located in the Chicago suburb of Lincolnshire. To date, it has presented over 135 productions, including original plays and re-imagined versions of Broadway classics. The Marriott Theatre for Young Audiences is another program created by the theater, which brings fairy tales and other original works to life for younger audiences to broaden outreach and make a positive impact through live theater.