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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.

Bike and Roll Chicago offers several locations to rent bicycles or Segways to explore the city. They provide five different tour options, such as The Amazing Lakefront, Friendly Neighbors, Chicago River & Parks, The Presidential Tour, and Bikes @ Nite, so you can pick the one that best suits your interests. Join one of their award-winning bike tours and see all the top attractions in Chicago. Glide along the stunning lakefront on a Segway. Please wear appropriate walking shoes as you embark on a magical adventure through downtown Chicago, lit with beautiful illuminations.

Emporium Arcade Bar is the original arcade bar and live events venue in Chicago that offers a variety of entertainment options. There's something for everyone, from classic arcade games to different pinball machines. The venue boasts a professional stage with sound and lights, where they regularly host live shows, DJs, game tournaments, and other events. Inside the venue, you'll find a thoughtfully curated bar with a selection of craft beers, an innovative cocktail program, and an extensive whiskey list. Whether you're planning a birthday celebration with a few friends or a company party, they offer flexible party solutions that can accommodate groups of all sizes. Emporium Arcade Bar is the perfect destination for anyone looking for an innovative entertainment experience. Join them for a night of fun and games, and discover why they are Chicago's best arcade bar and live events venue.

The Illinois Railway Museum is where you can learn about the history of railway transportation and its impact on the country. The Museum houses over 400 pieces of original equipment from when railroad transportation was essential for industrial purposes and everyday life in America. These pieces of equipment include horsecars, steam locomotives, and passenger cars. The Museum also exhibits and operates restored rolling stock and equipment on a demonstration rail line. Moreover, it collects, preserves, and maintains a reference library of publications, technical information, and other materials related to railroads, railways, and transportation for research and other purposes.