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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.

If you want a thrilling adventure on the Navy Pier, you must check out the Amazing Chicago Funhouse Maze. This attraction is a twisting labyrinth of mirrors, illusions, and surprises that will leave you dizzy with excitement. Covering over 4,000 square feet of tunnels and mazes, the Maze is a must-do for people of all ages. The Amazing Chicago Funhouse Maze has been open since 2001 and is a popular attraction among guests. It features classic funhouse elements such as a spinning tunnel and mirror maze, as well as new features like an infinity lightroom and glow light artwork. You will find plenty of unique photo opportunities throughout the Maze that you can't afford to miss.

If you want a unique entertainment experience in Chicago, consider visiting the historic Chicago Theatre. The theatre has been restored to its former glory and is now a popular venue for concerts and shows. It features a French Baroque design, crystal chandeliers, ornate artwork, and other decadent details. The iconic marquee of the theatre symbolizes the city and has been featured in countless works of art, photography, television shows, and movies. Apart from its rich history and stunning architecture, the Chicago Theatre is also a famous venue for live performances. It has hosted various events, including stage plays, magic shows, stand-up comedy, and musical acts. Many favorite artists have performed on its stage, including Frank Sinatra, Dolly Parton, Prince, and Kanye West, to name just a few.