Welcome, adventurous listeners, to Things to Do in Chicago, with your guide Oly Bennet—broadcasting live on this glorious Thursday, October 2, 2025. Today’s city vibes? Absolutely electric! Chicago’s waking up to balmy autumn temps bouncing from the upper 60s this morning to a toasty 80 by later today. Warm air means festival shirts, not flannel—so lose the parka, grab your sunglasses, and let’s dive into the day.

If you’re ready to squeeze every drop of joy out of a Chicago Thursday, I’ve got the quirkiest, coolest happenings on tap. First up, for those with taste buds that crave adventure, Port Wine Fest is pouring more fun than your uncle at Thanksgiving. From 5 to 8 p.m. at The Walden on West Walnut, over forty Portuguese wine producers uncork more than a hundred wines, including sparkling and legendary Ports—add in impossibly delicious bites and you’ve got an eat-and-sip extravaganza that doubles as a fundraiser for the Greater Chicago Food Depository. Swirl, sniff, and schmooze; tonight, your wine passport gets stamped Portuguese.

Next, music fans, warm up those air guitars—the Chicago Theatre is set to explode tonight when Queens of the Stone Age rock the house, joined by none other than Paris Jackson. The Catacombs Tour hits the historic State Street stage—doors open early, digital tickets ready, and if you’ve never been inside this legendary temple of tunes, tonight’s your chance for a legendary night out.

For families or anyone itching for a classic Midwest fall day, the Fall Festival at Sonny Acres Farm in West Chicago is pure pumpkin-powered bliss. From hayrides and mini roller coasters to roasted corn, taffy apples, and haunted barns that’ll have even the bravest adults squealing louder than the kids, this fest is open every day through October—a cornucopia of smile-inducing fun.

Cultural buffs, you’ll want to pencil in World Music Wednesdays at Old Town School of Folk Music—which continues as part of Chicago’s World Music Festival, serving global rhythms and dance with a local twist. Trust me, your Spotify playlist will never recover.

In today’s local headlines, the city’s showing off its global flavor with new restaurant alerts—word on Randolph Street is a brand-new Korean BBQ joint is firing up grills for both carnivores and veggie-lovers. Transit-wise, no major delays reported, but keep in mind some late-night work on the Red and Blue lines as part of CTA’s autumn upgrades.

Can’t-miss-moments for the day? Stroll Millennium Park, selfie in front of the Bean (bonus points for goofy poses), and, if you’re a thrill seeker, detour to the 360 CHICAGO observation deck for edge-of-your-seat views that’ll make your friends think you’ve scaled the Willis Tower with Spiderman agility. Feeling extra bold? The hidden gem of Garden of the Phoenix in Jackson Park is an oasis of Zen with autumn leaves twirling in technicolor.

Local tip: Hungry but hate waiting in line? Savvy Chicagoans use mobile order apps for deep-dish at Lou Malnati’s or grab snack-sized Italian beefs at iconic stands—always go hot and sweet with your giardiniera, trust me!

Before you dash, get your calendars ready—Open House Chicago returns October 18-19 with rare access to secret rooftops, hidden vaults, and the stories behind the city’s boldest buildings. And rumor has it, tomorrow's lineup includes a moonlit river boat party plus the return of Chicago's secret pop-up ping pong bar. Curious? Tune in tomorrow for the latest scoop.

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