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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.

Discover the hidden gem of the Chicago Magic Lounge, where a blend of magic and sophistication awaits you. It's the perfect place for a thrilling, unforgettable night of mystery and entertainment. Whether celebrating a special event, planning a romantic date night, or looking for a unique outing with friends, the Chicago Magic Lounge offers an experience like no other. As soon as you step inside, you'll leave the ordinary behind and enter a secret laundry entrance into a luxurious retro-inspired "speakeasy." Here, you can indulge in handcrafted cocktails and savor delectable small plates while enjoying some of the most impressive acts performed by the finest magicians in the industry. It's a unique opportunity to witness the art of magic up close and personal, and you'll be amazed by the genuine moments of astonishment that await you.

Navy Pier, built in 1916, was the largest in the world at that time. It served as a docking area for passenger excursion steamers and cargo ships. During both World Wars, Navy Pier was utilized for military purposes such as housing, training, and more. In its non-military role, the pier had many attractions, including a streetcar line, theater, emergency room, picnicking areas, dance hall, auditorium, children's playground, and more. Navy Pier, which sits on the lakefront, occupies approximately 50 acres of land, with sprawling parks, gardens, and sculptures on the lawns. The attraction also has several shops and restaurants. Navy Pier offers a variety of activities, including boat parades, air shows, sightseeing tours, festivals, and fireworks, making it the most popular tourist attraction in Chicago.

If you are a fan of blues music, you should visit Kingston Mines during your trip to Chicago. This jazz and blues bar is one of the oldest establishments in the city and offers an intimate setting for live music performances. The venue has been presenting the best acts since 1968 and has a legendary reputation for hosting some of the finest live music performances in Chicago. It has won the "Best Blues Club" award at the Chicago Music Awards for 13 years. At Kingston Mines, you can enjoy live, authentic jazz and blues music on two stages. The venue also offers a wide selection of drinks, including beer buckets, wine, and cocktails. And if you're feeling hungry, check out Doc's Rib Joint - the in-house restaurant that serves mouthwatering barbecue, chicken, burgers, seafood, ribs, and various tasty sides and appetizers.