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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.

The Willis Tower, previously known as the Sears Tower, is in downtown Chicago. Completed in 1974, it is a 108-story building that held the title of the tallest building in the world for nearly 25 years. It remains the tallest building in the United States. The Skydeck, located on the 103rd floor, is the building's observation deck, approximately 1,353 feet above the ground. It is one of Chicago's most popular tourist attractions, welcoming about 1.3 million visitors annually. Recently, renovations have introduced new glass balconies with floors extending four feet over the street. The balcony provides stunning views of Illinois, Lake Michigan, and neighboring states Indiana, Michigan, and Wisconsin on a clear day.