Welcome, listeners, to Things to Do in Chicago with Oly Bennet, your globe-trotting, sports-obsessed guide to the world’s quirkiest adventures! It’s Friday, October 31st, and Chicago is feeling deliciously electric—Halloween’s got the Windy City in full-on costume mode, with crisp fall air, pumpkin-scented breezes, and that thrilling tingle that only comes when everyone, everywhere, is ready to party!

If you’re wondering what’s cooking in the city today, it’s a cauldron of culture, fun, and chills. Let’s start with The Other Art Fair at Artifact Events in Ravenswood. Today only, this art fest transforms into an art-powered Halloween bash, with DJs, a wild butterfly taxidermy workshop led by The Insect Asylum, tintype portraits, and a full-on costume contest. More than 115 independent artists are strutting their stuff—a top pick for anyone looking to get weird and creative today, according to Secret Chicago.

If you’re chasing that classic spooky spirit, the Haunted Halsted Halloween Parade is marching across Northalsted tonight. Think giant puppets, eye-melting costumes, stilt walkers, and enough glitter to cover Grant Park twice. This is not just a parade, it’s an all-ages showstopper with a prize-packed costume contest. Looking for more rising heart rates? The Chapel of the Undead Costume Event at Sound Bar is Chicago’s late-night answer to “What if a vampire nightclub met a DJ rave?”—pure, unfiltered nighttime madness.

For families, there’s no shortage of candy-crazed action. Brookfield Zoo is running “BOO! At the Zoo”—trick-or-treating, spooky inflatables, magicians, and haunted treats from morning to evening. West Town’s Jack’s Pumpkin Pop-Up is a pumpkin-palooza with corn mazes, axe throwing, and enough pumpkins to build a Cubist sculpture. Want something more community-powered? Head to El Paseo Boricua for the Haunted Paseo, a free, family-friendly fiesta with food, games, and a community haunted house. There’s even a Trunk or Treat event at Paschen Park, where your best costume might land you extra sweets.

Sometimes, Chicago just keeps the fun rolling with concert and nightlife choices that will launch you into November wide awake. The House of Blues is conjuring House of Boos, a jam-packed music bonanza, while Chicago Eagle hosts BEEFWITCH, a legendary occult underwear party making its first windy city appearance tonight, promising goth pop, dance rituals, and a midnight floor show.

On the city beat, in case you missed it, the Red Line “L” trains are running extra service for tonight’s festivities, with late-night trains and security teams to help costumed commuters bounce from party to parade and back. Restaurant hounds, listen up: Avli River North recently unveiled a spooktacular Greek-inspired Halloween menu, and JoJo’s Shake Bar has transformed into a wild pumpkin patch, serving outrageous milkshakes alongside bonkers fall treats.

My must-dos for the restless and bold? If you’ve never Instagrammed from The Bean at midnight in costume, tonight’s the night—with a rumored flash mob dance-off in Millennium Park after the parade. Want a local gem? The WNDR Museum, an ever-evolving interactive art wonderland, is running a special “Glow Night” experience—bring a friend and see who can dance the wildest on the LED Light Floor.

Pro tip: In Chicago, the best bathrooms during parade nights are at the Chicago Cultural Center—clean, roomy, and open late. And did you know the city’s Halloween parade tradition dates back to 1920, when revelers marched down State Street dressed as… radishes? True story, and a reminder: Chicago weird is Chicago wonderful.

Don’t dash off yet—tomorrow’s bringing the Little Village Arts Festival, Day of the Dead magic at the National Museum of Mexican Art, and fresh harvest fun at neighborhood farmers markets. I’ll be back with more wild picks, untold stories, and epic Chicago quirks.

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