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Naper Settlement is an outdoor museum showcasing downtown Naperville's rich history. Spread over 13 acres, it offers visitors a unique opportunity to connect with the area's cultural heritage and foster a sense of community. The museum's vision is to encourage conversations, enrich educational opportunities, and provide engaging experiences for visitors, businesses, and the local community. Naper Settlement is an excellent place for families to visit as it offers interactive learning opportunities for people of all ages. The site boasts 30 historic buildings that visitors can explore to learn about the connections between the past and present. Additionally, the museum hosts special events, programs, and on-site activities throughout the year, giving visitors a unique chance to engage with the area's rich cultural heritage.

If you're a fan of Shakespeare, you should attend the Chicago Shakespeare Theater on Navy Pier. This professional theater company was founded in 1986 by Barbara Gaines and is the third largest in the Midwest. They produce works from the Shakespeare canon and other theatrical performances, with over six hundred performances annually at the Courtyard Theater and the Upstairs space. The theater has won numerous awards, including 36 Joseph Jefferson Awards, three Laurence Olivier Awards, and a Regional Theatre Tony Award. The theater also has a family series for younger audiences and special student pricing.

Celebrate the holiday season with the nationally televised Chicago Thanksgiving Parade, which has been ranked the second-best Thanksgiving Parade in the country by Time Out Magazine. Witness the excitement as talented marching bands, majestic equestrian units, national celebrities, and spectacular performance groups march through downtown Chicago. Why settle for watching a parade meander through New York City on TV when you can see giant cartoon-character balloons, marching bands, and dancers on the streets of Chicago? If you are in the city on Thanksgiving, you can catch the annual procession before indulging in your turkey. The Parade moves down State Street between Ida B. Wells Drive and Randolph Street and ends by 11 am, providing you with ample time to return home and assist with the cooking. The event commemorates Thanksgiving with a three-hour procession of giant balloons, marching bands, dancers, and more.