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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.

If you want to have a good laugh and witness some of the best comedic talents in the show business, you should visit The Second City Theater. This theater has been the breeding ground for many famous comedians like John Belushi, John Candy, Bill Murray, Dan Aykroyd, Gilda Radner, Mike Myers, Chris Farley, Steve Carell, Stephen Colbert, and Tina Fey. The Second City is an improvisational comedy company that started in Chicago. The company has stages in Toronto and Los Angeles, 11 touring ensembles, and training centers and programs in other cities. The performances are semi-improvised and feature scripted material with new content added after the second act, often based on audience suggestions

The Apollo Theater is a must-visit attraction in Chicago for anyone who loves live theater. Located in Lincoln Park, the theater has provided an intimate setting for live performances since 1978. It has two stages that offer classic and contemporary plays, allowing you to experience the best of the theater world up close. The company produces shows perfect for families and draws nearly 50,000 people annually. The Chicago Sun-Times has named the Apollo the most innovative theater in Chicago for families. So, whether you're looking for a fun and educational experience for your family or want to enjoy a night out with friends, head over to the Apollo Theater and enjoy some of the best live theater that Chicago has to offer.