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If you want to experience Greek culture, Chicago's Greektown is a must-visit neighborhood. This vibrant district offers a variety of nightlife spots, restaurants, gift shops, and galleries that celebrate Greek heritage. It's the best place to sample Greek culture outside of Athens and has become the city's go-to destination for Greek food, nightlife, and rich cultural traditions. With many establishments dedicated to preserving old-world traditions, visitors can truly immerse themselves in Greek culture in this neighborhood. Apart from dining and nightlife, visitors can explore The National Hellenic Museum, ride the Greektown Trolley, witness the annual Greek Independence Day parade, and indulge in the Taste of Greece festival. These activities make Greektown the perfect destination for anyone interested in learning more about Greek heritage in Chicago.

If you're a fan of Shakespeare, you should attend the Chicago Shakespeare Theater on Navy Pier. This professional theater company was founded in 1986 by Barbara Gaines and is the third largest in the Midwest. They produce works from the Shakespeare canon and other theatrical performances, with over six hundred performances annually at the Courtyard Theater and the Upstairs space. The theater has won numerous awards, including 36 Joseph Jefferson Awards, three Laurence Olivier Awards, and a Regional Theatre Tony Award. The theater also has a family series for younger audiences and special student pricing.

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.