Halloween in Chicago: Sports, Parades, and Underground Parties on October 31, 2025
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But Chicago’s not just about the big leagues. The Haunted Halsted Halloween Parade kicks off at 7:30 PM from Halsted and Belmont, winding its way through Northalsted with drag queens, dancers, and thousands of costumed revelers. Stick around for the costume contest at 8:30 PM and join the after-party scene at local bars—this is where the city’s creative spirit truly shines. If you’re looking for something more family-friendly, the Trunk or Treat event at 4008 W Madison St runs from 4 PM to 7 PM, offering free skating, food, candy, and face painting for all ages.
For a quirky twist, head to the Chicago Eagle for BEEFWITCH: Halloween, a goth and girl pop party with a midnight floor show and DJ NaughtyBoyy spinning witchy vibes—black underwear and eyeliner encouraged. If you’re into underground sports, check out the local flag football leagues or catch a pickup basketball game at FFC Gold Coast, where the Hopsmith Basketball League is always welcoming new players.
Art lovers can explore the city’s vibrant galleries or join the Halloween and Beadmaking event at Murray Park from 3:30 PM to 5:30 PM, a free, hands-on activity perfect for kids and crafty adults. For a taste of Chicago’s culinary scene, hit up the Salt Shed for a live music show with Lil Tecca, or grab a bite at one of the city’s legendary deep-dish pizzerias before heading out for the night.
Chicago’s Halloween is a mix of tradition and innovation, from the Bears’ NFL FLAG Regional Tournament pumping energy into the community to the city’s iconic haunted houses and pop-up bars. Whether you’re cheering on your favorite team, dancing at a themed party, or exploring hidden gems, there’s something for everyone in this vibrant city.
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