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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 Chicago Latino Film Festival is a nonprofit organization that aims to promote and raise awareness of Latino cultures through various art forms and education. One of their main events is the Chicago Latino Film Festival, which showcases about 100 films from Latin America, the Caribbean, Spain, Portugal, and the US. The Festival allows film enthusiasts in Chicago, regardless of their backgrounds, to watch movies they may not have seen otherwise. The movies featured in the Festival include films that have gained global recognition on the festival circuit, box office hits in their countries of origin, and those that have yet to be released in theaters. The Festival initially premiered with 14 films projected onto a concrete wall, drawing an audience of 500 people. Apart from films, the Festival also features music, dance, comedy, theater, and visual arts, making it a comprehensive celebration of Latino culture.

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.