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If you're a fan of blues music, you will want to attend Buddy Guy's Legends in Chicago. This iconic blues bar is owned by the legendary blues musician Buddy Guy himself, and it's one of the best places in the country to catch a live blues performance. Over the years, some of the biggest names in music have graced the stage at Buddy Guy's Legends, including Van Morrison, Bo Diddley, The Rolling Stones, Lou Rawls, ZZ Top, John Mayer, Stevie Ray Vaughan, and many more. It's a must-visit spot for music lovers visiting Chicago.

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 360 Chicago Observation Deck is a must-visit attraction for anyone looking to enjoy a stunning 360-degree view of Chicago's Magnificent Mile. Located at 1,000 feet, the observation deck provides breathtaking panoramic views of the city and surrounding areas. You can see up to 80 miles and four neighboring states from the lookout. For those not afraid of heights, the deck also features Chicago's only open-air skywalk, which offers a thrilling sensation of looking down. While enjoying the breathtaking views of the city, you can relax and sip on a refreshing drink. Additionally, the observation deck offers TILT, the highest thrill ride in Chicago.