Welcome, listeners, to Things to Do in Chicago—your daily dose of windy city adventure with me, Ollie Bennet! It's Friday, October 24, 2025, and Chicago is waking up to crisp, fall perfection. The air is brisk—morning temps in the low 40s, climbing to the low 50s under a mix of sunshine and scattered clouds. No rain, no snow, just pure autumn glory. There's a freeze warning in some areas, so if you're headed out early, grab your funkiest sweater—this is the city where fashion meets frostbite.
Now, the vibe out here is pure energy. The streets are buzzing with pre-Halloween anticipation, the aroma of pumpkin lattes wafting from every corner café, and the riverwalk sparkling under those cool blue skies. Let’s get you plugged into Chicago’s epic calendar for the day!
First up, comedy fans are in for a treat tonight as Nate Bargatze brings his Big Dumb Eyes World Tour to the United Center. According to The Atlantic, Bargatze is “The Nicest Man in Stand-Up”—and judging by Chicago’s ticket frenzy, the city’s ready for a night of gut-busting laughter. Show starts at 7PM, with a pre-party kicking off at 5PM—private entry, DJ sets, free cocktails, exclusive merch. To get there, you’ve got CTA buses, Blue, Green, and Pink Lines all rolling and plenty of parking if you're still rocking that vintage 2002 Civic.
But wait, culture vultures—slide over to the Chicago Cultural Center tonight for DCASE's Under the Dome. Local musicians Rich Robbins and Demetruest headline live under the dazzling Tiffany glass dome, with a Chicago Fair Trade clothing swap happening alongside. No ticket needed, doors open at 5PM, and it’s an all-ages bash—so even grandma can catch the groove.
If you’ve got a wild child with you (or you are one yourself), Lincoln Park Zoo is hosting Adults Night Out: Howl-o-ween. This after-hours creature feature is a one-of-a-kind night for grownup goblins—think zoo cocktails, haunted habitats, a lot of howling at the moon.
Craving music? Don Broco lays it down at House of Blues at 7PM, and Schubas and Lincoln Hall explode with indie and local acts all weekend. The Infinite Wrench at the Neo-Futurist Theater promises 30 rapid-fire plays in 60 minutes—true Chicago-style artistic chaos.
News flash—Chicago’s transit system is running smooth with extra service for big event nights. If your taste buds want adventure, rumor has it there’s a new taqueria opening in the West Loop, featuring not just tacos, but a guacamole bar. Yes, Chicago knows how to win hearts.
For today's must-dos: cruise Millennium Park for leaf-peeping and selfie central under The Bean, check out the farmer’s market at Daley Plaza until 2PM—stock up on apples, cider, and stories from folks who know every secret about the city. And if you’re a true offbeat-sports seeker, ask around about the legendary Chicago Squash Ball—an obscure game played underground since 1985 where the only rule is chaos. If you find it, report back—I’ll trade you three fun facts and a signed hot dog napkin.
Here's a fun local tip: “The Loop” isn’t just a name—it refers to the circuit of elevated train tracks downtown. If you ride a full loop, some folks claim you gain temporary superpowers. Effects may vary. Bragging rights, guaranteed.
Looking ahead—tomorrow Gallagher Way explodes with the Pumpkin Party from 1 to 5PM. Costume parade, pumpkin crafts, and haunted hilarity for all ages. And with the Chicago International Film Festival rolling all weekend, tune in tomorrow for more wild picks, celebrity sightings, and hidden gems.
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