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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.

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.

Old St. Patrick's Church is a historical landmark in Chicago that was designed to withstand the test of time. Built in the 1850s, it is among the few structures that survived the devastating Great Chicago Fire of 1871. The church's architecture is rooted in the Celtic Revival movement, making it an outstanding example of Chicago's unique architectural style. Today, Old St. Patrick's Church is a vibrant community of more than 3,000 members, warmly welcoming visitors from diverse backgrounds. Located at the intersection of Chicago's diversity, the church celebrates its rich historical legacy while looking toward a promising future. Apart from Sunday masses, the church organizes guided tours and annual block parties, fostering community and joyous celebration.