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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 are a fan of blues music, you should visit Kingston Mines during your trip to Chicago. This jazz and blues bar is one of the oldest establishments in the city and offers an intimate setting for live music performances. The venue has been presenting the best acts since 1968 and has a legendary reputation for hosting some of the finest live music performances in Chicago. It has won the "Best Blues Club" award at the Chicago Music Awards for 13 years. At Kingston Mines, you can enjoy live, authentic jazz and blues music on two stages. The venue also offers a wide selection of drinks, including beer buckets, wine, and cocktails. And if you're feeling hungry, check out Doc's Rib Joint - the in-house restaurant that serves mouthwatering barbecue, chicken, burgers, seafood, ribs, and various tasty sides and appetizers.

The Museum of Science and Industry is a fascinating place to visit if you want to learn more about the Earth, the human body, technology, and science. With over 2,000 exhibits spread across 75 halls that cover about 14 acres, the museum opened in 1933 and is now the biggest science museum in the Western Hemisphere. In 2009, the museum had a record attendance of over 1.6 million guests, making it the third-largest cultural attraction in Chicago. The museum has a range of permanent exhibits, including a working coal mine, a 3,500-square-foot model railroad, a German Submarine captured in World War II, and a NASA spacecraft used for the Apollo 8 mission in 1968. Additionally, visitors can experience flight simulators, military crafts, an assembly line replica, a 40-foot water vapor tornado, a 13-foot interactive heart, and much more.

The Wells Street Art Festival is an annual event on the second weekend of June. It is located in Old Town's popular Wells Street corridor and attracts around 50,000 visitors yearly. The festival showcases talented artists from across the continent specializing in traditional painting, sculpture, artisan woodworking, metalsmithing, jewel crafts, digital arts, and more. Additionally, there is a dedicated performance stage where local musicians, performance artists, and cover/tribute bands entertain the crowd throughout the weekend. Moreover, at the corner of Wells Street and Evergreen Street is a children's play area where kids can participate in arts and crafts, watch a performance, or have fun. The festival also has over 20 food and drink vendors who sell a variety of tasty treats. Visitors can try something from all the excellent Old Town restaurants participating.