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The Apollo Theater is a must-visit attraction in Chicago for anyone who loves live theater. Located in Lincoln Park, the theater has provided an intimate setting for live performances since 1978. It has two stages that offer classic and contemporary plays, allowing you to experience the best of the theater world up close. The company produces shows perfect for families and draws nearly 50,000 people annually. The Chicago Sun-Times has named the Apollo the most innovative theater in Chicago for families. So, whether you're looking for a fun and educational experience for your family or want to enjoy a night out with friends, head over to the Apollo Theater and enjoy some of the best live theater that Chicago has to offer.

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.

The Illinois Railway Museum is where you can learn about the history of railway transportation and its impact on the country. The Museum houses over 400 pieces of original equipment from when railroad transportation was essential for industrial purposes and everyday life in America. These pieces of equipment include horsecars, steam locomotives, and passenger cars. The Museum also exhibits and operates restored rolling stock and equipment on a demonstration rail line. Moreover, it collects, preserves, and maintains a reference library of publications, technical information, and other materials related to railroads, railways, and transportation for research and other purposes.