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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.

Visiting the Chicago Children's Theatre with your family is a beautiful way to experience classic fairy tales, and children's stories brought to life on stage. The theatre is committed to enhancing the community through diverse and meaningful theatrical and educational programs that engage and inspire children and adults alike. Their goal is to become the leading professional theatre company in Chicago, producing spectacular productions and programs that promote inclusivity and accessibility while motivating young people and families to lead adventurous, courageous, and curious lives. If you're in the vicinity, be sure to attend their shows, such as A Year with Frog and Toad and If All the World Were Paper.