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If you're a fan of blues music, you will want to attend Buddy Guy's Legends in Chicago. This iconic blues bar is owned by the legendary blues musician Buddy Guy himself, and it's one of the best places in the country to catch a live blues performance. Over the years, some of the biggest names in music have graced the stage at Buddy Guy's Legends, including Van Morrison, Bo Diddley, The Rolling Stones, Lou Rawls, ZZ Top, John Mayer, Stevie Ray Vaughan, and many more. It's a must-visit spot for music lovers visiting Chicago.

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.