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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 want to have a good laugh and witness some of the best comedic talents in the show business, you should visit The Second City Theater. This theater has been the breeding ground for many famous comedians like John Belushi, John Candy, Bill Murray, Dan Aykroyd, Gilda Radner, Mike Myers, Chris Farley, Steve Carell, Stephen Colbert, and Tina Fey. The Second City is an improvisational comedy company that started in Chicago. The company has stages in Toronto and Los Angeles, 11 touring ensembles, and training centers and programs in other cities. The performances are semi-improvised and feature scripted material with new content added after the second act, often based on audience suggestions