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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.

If you plan a trip to Chicago, visiting The Art Institute of Chicago should be at the top of your to-do list. Established in 1879, it boasts an extensive collection of African sculptures, medieval and Renaissance armor, and an array of Aztec, Greek, Roman, and Byzantine artworks. The museum is home to some of the world's most famous and recognizable pieces of art, such as "A Sunday on La Grande Jatte," "American Gothic," Vincent van Gogh's "Self-Portrait," and original Monets. You will be captivated by these works of art's sheer beauty and grandeur. The Art Institute of Chicago is one of the world's oldest and largest art museums, founded in 1879. It is in the Art Institute of Chicago Building in Grant Park, Chicago. According to Wikipedia, the museum collects, preserves, and interprets works of art of the highest quality, representing the world's diverse artistic traditions for the inspiration and education of the public and by the profession's highest ethical standards and practices.