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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.

Chicago's Best Standup Comedy is back and better than ever before. The comedy club has assembled an outstanding lineup of comedians you won't find anywhere else in the city. From the biggest names in the business to local talent, there's something for everyone's taste and style of comedy. Since 1979, the world-renowned Laugh Factory has entertained audiences and is recognized as the "#1 comedy club in the country" by USA Today. The Laugh Factory has brought laughter to millions of people around the world. It's a place where locals and tourists can go for an evening of guaranteed smiles and where comedy's most prominent stars visit to feel like they're part of comedy history. With features like a comedy magazine and a historic stage, the Laugh Factory has helped launch the careers of countless comedians and continues to nurture up-and-coming talent.

The Willis Tower, previously known as the Sears Tower, is in downtown Chicago. Completed in 1974, it is a 108-story building that held the title of the tallest building in the world for nearly 25 years. It remains the tallest building in the United States. The Skydeck, located on the 103rd floor, is the building's observation deck, approximately 1,353 feet above the ground. It is one of Chicago's most popular tourist attractions, welcoming about 1.3 million visitors annually. Recently, renovations have introduced new glass balconies with floors extending four feet over the street. The balcony provides stunning views of Illinois, Lake Michigan, and neighboring states Indiana, Michigan, and Wisconsin on a clear day.