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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'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.

Maggie Daley Park Rock Climbing is Chicago's first and only Climbing Park. It features two magnificent custom-designed rock climbing structures that offer a unique outdoor recreational experience for beginners and experts alike. The park staff provides instructions and supervision to ensure the safety of the climbers. The combination of Skating Ribbon and Climbing Park makes it an all-season park inviting and engaging for Chicagoans and visitors. The climbing walls are 40 feet high and cover an area of 19,000 square feet. The wall is divided into beginner and advanced sections, and there are three types of climbing: bouldering, lead-harnessed, and top rope. The climbing wall can comfortably accommodate 25 to 100 climbers at any given time.