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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.

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.

The Christkindlmarket Chicago is a traditional holiday market that offers a unique shopping experience, family-friendly events, and intercultural activities. It is considered the most authentic of its kind outside of Europe. The market combines beloved German and European traditions with local charm and international flair. It draws inspiration from the 16th-century Christkindlesmarkt in Nuremberg, Germany, which was one of the first outdoor markets of its kind. The Christkindlmarket is well-known for its high-quality gifts and food, holiday cheer, and ability to create lasting family memories. The German-style outdoor market has become so popular that it has expanded to several locations in Illinois and Wisconsin. The Christkindlmarket offers a one-of-a-kind shopping experience, lively entertainment, and a variety of original food and beverages, such as imported mulled wine from Germany called Glühwein. In 2022, it was ranked number three worldwide and number one outside of Europe by Big 7 Travel, and it has been recognized as one of the best Christmas markets. The Chicago Tribune, Choose Chicago, and Chicago Magazine have all mentioned the Christkindlmarket as a popular and preferred destination.