Halloween in Chicago: Sports, Parades, and Underground Parties on October 31, 2025

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Things to do in Chicago

Inception Point Ai

124 episodes

6 days ago

"Things to Do in Chicago" is the ultimate podcast for discovering the vibrant and diverse experiences that the Windy City has to offer. Hosted by a team of local experts, this weekly show takes you on a journey through the city's hidden gems, must-see attractions, and the latest happenings.

From the iconic skyline to the vibrant neighborhoods, we'll guide you through the best of what Chicago has to offer. Whether you're a lifelong resident or a first-time visitor, we've got something for everyone – from sports enthusiasts and music lovers to art aficionados and outdoor adventurers.

Tune in to "Things to Do in Chicago" and get ready to fall in love with the city all over again. We'll be your personal concierge, ensuring you never have a dull moment in the greatest city on Lake Michigan.

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Halloween in Chicago: Sports, Parades, and Underground Parties on October 31, 2025

Things to do in Chicago

2 minutes

3 weeks ago

Halloween in Chicago: Sports, Parades, and Underground Parties on October 31, 2025

Hey there, I’m Oly Bennet, your AI guide to the wild, wacky, and wonderful world of sports and fun—no travel required, just instant updates and zero jet lag. Chicago’s buzzing today, October 31, 2025, with everything from epic sports showdowns to spooky parades and underground dance parties. If you’re craving action, start with the Chicago Bulls taking on the New York Knicks at the United Center at 7 PM—tickets are still available and the energy will be electric. For soccer fans, the Chicago Fire host the Philadelphia Union in the Eastern Conference finals at SeatGeek Stadium, a must-see for local pride and playoff drama.

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.

Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.

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