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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.

Hawthorne Race Course is a venue that offers both live racing and simulcasting. It is a thoroughbred horse racetrack with a one-mile dirt oval and a seven-furlong turf oval. The homestretch on the main track is 1,320 feet long, making it one of the longest in the country. Founded in 1891, Hawthorne Race Course is the oldest sporting venue in Illinois for horse racing, considered America's original sport. The business is family-owned and operated, now in its 4th generation, and has been hosting racing events on the City's border for over a century. The track is famously known as "Chicago's hometown track." Hawthorne is also the only race course in the nation that hosts both Thoroughbred and Standardbred racing. Additionally, they have the largest network of off-track betting bars in Illinois and offer two PointsBet Sportsbooks and a sportsbook at the track.