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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.

For over 80 years, Wendella has been Chicago's top provider of tours and cruises on the River and Lake Michigan. Their tours offer the perfect blend of nostalgia for the city's rich history and modern experiences, making it an enjoyable day on the water for visitors and locals alike. As the original architecture tour in Chicago, Wendella offers a variety of narrated tours that focus on the city's architectural heritage and history. Their knowledgeable tour guides provide detailed accounts of the 130-year-long history behind the iconic skyline, while the staff ensures that you are comfortable and entertained throughout the journey. This tour takes you through the city's heart on all three branches of the Chicago River, providing an up-close look at the iconic buildings and structures that define the city.