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The Auditorium Theatre of Roosevelt University is an incredibly historic venue that is worth a visit. This entertainment space has been around for over a century. It has hosted various performances, from classical orchestras like the Chicago Symphony Orchestra to legendary rock acts like Jimi Hendrix, Pink Floyd, and Eric Clapton. As a National Historic Landmark and a Chicago Landmark, the Auditorium Theatre is an integral part of the city's history. It was once home to the Chicago Symphony Orchestra and the Chicago Civic Opera. After reopening in 1967, it quickly became a premier venue for rock stars like Janis Joplin, Bob Marley, and many others. If you find yourself in Chicago, a trip to the Auditorium Theatre is a must-see. Not only is it a beautiful and historic venue, but it's also an essential part of the city's cultural heritage.

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.