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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.

Lollapalooza is a music festival that features over 170 bands across nine stages worldwide. The festival takes place in Grant Park, located in the heart of downtown Chicago, with the stunning Chicago skyline serving as a backdrop. In addition to the impressive lineup, Lolla offers interactive areas where attendees can participate in giveaways, purchase merchandise, and more. Chow Town, the festival's food area, features delicious food, drinks, and sweets from some of Chicago's favorite restaurants. The emphasis is on fresh, reasonably priced items from local vendors rather than the typical "carnival" fare. For those looking to elevate their Lolla experience, you can purchase GA+, VIP, or Platinum tickets, which provide access to prime views, exclusive lounges, luxury amenities, and getaways from the crowds.

If you are a lover of art, then you must visit the Museum of Contemporary Art Chicago. The museum has a vast collection of contemporary art by famous artists like Jasper Johns, Chuck Close, Francis Bacon, and Andy Warhol. What makes this museum a must-visit is its commitment to showcasing new and experimental work in all forms of media. Additionally, the museum has ambitious learning programs that are worth exploring. The museum showcases present-day artists' work and ideas. Additionally, it strives to conserve contemporary art for future generations. In 1974, the museum expanded its mission to include the procurement and preservation of modern artwork, and its collection has since grown to feature over 2,000 works. With a focus on community engagement, the MCA aims to foster dialogue, learning, and growth opportunities for current and future art enthusiasts.