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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 are a lover of art, then you must visit the Museum of Contemporary Art Chicago. The museum has a vast collection of contemporary art by famous artists like Jasper Johns, Chuck Close, Francis Bacon, and Andy Warhol. What makes this museum a must-visit is its commitment to showcasing new and experimental work in all forms of media. Additionally, the museum has ambitious learning programs that are worth exploring. The museum showcases present-day artists' work and ideas. Additionally, it strives to conserve contemporary art for future generations. In 1974, the museum expanded its mission to include the procurement and preservation of modern artwork, and its collection has since grown to feature over 2,000 works. With a focus on community engagement, the MCA aims to foster dialogue, learning, and growth opportunities for current and future art enthusiasts.

Navy Pier, built in 1916, was the largest in the world at that time. It served as a docking area for passenger excursion steamers and cargo ships. During both World Wars, Navy Pier was utilized for military purposes such as housing, training, and more. In its non-military role, the pier had many attractions, including a streetcar line, theater, emergency room, picnicking areas, dance hall, auditorium, children's playground, and more. Navy Pier, which sits on the lakefront, occupies approximately 50 acres of land, with sprawling parks, gardens, and sculptures on the lawns. The attraction also has several shops and restaurants. Navy Pier offers a variety of activities, including boat parades, air shows, sightseeing tours, festivals, and fireworks, making it the most popular tourist attraction in Chicago.