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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.

The National Veterans Art Museum is committed to collecting, preserving, and exhibiting art created by military personnel inspired by their experiences during active duty. The museum's focus is mainly on the Vietnam War, and its primary goal is to increase the public's understanding of the impact of conflict. By showcasing artworks created by military veterans, the museum aims to encourage dialogue about the effects of war, including its physical, mental, and emotional consequences. Since its establishment, the museum has amassed a significant collection of artwork created by veterans who have served in various wars, including WWII, Korea, the Gulf War, and the Global War on Terror. The collection now comprises over 2,000 pieces, a considerable increase from the 700 works created by 115 artists who served in the Vietnam War. These veterans come from different parts of the world, such as the United States, Australia, Cambodia, Hungary, Thailand, and North and South Vietnam. The museum's collection includes paintings, drawings, photography, sculpture, and literary works by military writers like Kurt Vonnegut and Tim O'Brien. The museum also offers interactive exhibitions, allowing visitors to engage with the ideas and themes presented.

Hawthorne Race Course is a venue that offers both live racing and simulcasting. It is a thoroughbred horse racetrack with a one-mile dirt oval and a seven-furlong turf oval. The homestretch on the main track is 1,320 feet long, making it one of the longest in the country. Founded in 1891, Hawthorne Race Course is the oldest sporting venue in Illinois for horse racing, considered America's original sport. The business is family-owned and operated, now in its 4th generation, and has been hosting racing events on the City's border for over a century. The track is famously known as "Chicago's hometown track." Hawthorne is also the only race course in the nation that hosts both Thoroughbred and Standardbred racing. Additionally, they have the largest network of off-track betting bars in Illinois and offer two PointsBet Sportsbooks and a sportsbook at the track.