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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.

The Hideout is not your typical bar; it's a place where everyone is welcome, regardless of whether they fit in. This prohibition-era bar may be small, but it's been a community space for independent music and performance in Chicago for over 25 years. On Saturdays, you can enjoy live music and dancing at The Hideout. It's a hub for music, art, performance, plays, poetry, rock, and rebellion. The bar is rooted in complex, hard-playing, creative artistic expression and intellectual freedom. It's more New Deal than New Age, and while it's not for everyone, it's for anyone who wants to experience something unique and authentic.

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.

If you're looking for a fun and challenging water adventure, consider trying stand-up paddleboarding or SUP, which are available at Chicago SUP. They offer rentals, lessons, yoga, fitness classes, expeditions, and group activities for fun in the sun. SUP is a hybrid of surfing and kayaking, where you stand on an oversized surfboard and paddle with a single-bladed paddle. It's a sport that anyone can enjoy and offers a unique and fun way to exercise. SUP is a family-friendly activity that provides an unparalleled full-body workout. Many professional athletes even use SUP during their off-season training routines. So why not give it a try and supplement your workout regime?