Welcome, brilliant listeners, to another adrenaline-pumped, thrill-packed episode of Things to do in Chicago! It’s Thursday, October 23, 2025, and I’m your globe-trotting, high-fiving, sports-obsessed pal Oly Bennet, here to make your day as lively as a Wrigleyville bar on game day.
Let’s dive right in: Today, Chicago is buzzing like a marathon runner who just chugged three espressos. Crisp autumn air has the city wrapped in electric sweater weather, but the sun’s out, and the energy is all go. If you’re into a little cloud drama with your plans, you might get those dramatic Lake Michigan skies, straight out of a sports movie montage.
Now cue the wild mix of today’s events—Chicago’s always serving something for everyone. For job-seekers or folks craving new horizons, the Congress Plaza Hotel is hosting the Chicago Job Fair from 11 till 2. This is your shot to network like a pro and maybe land a gig before your next hot dog according to Eventbrite.
Cultural explorers, polish those jazz hands and jog down memory lane: The Copernicus Center is celebrating with David Meulemans’ 65th Birthday Benefit for Chicago Cabaret Professionals tonight. It’s got music, witty banter, and all the showbiz glitz you’d expect from a city that gave birth to improv legends, as highlighted on the Copernicus Center’s site.
Love a good market and the smell of fresh produce with your midday hustle? The Daley Center’s famous Farmer’s Market is open till 2 p.m. Squeeze some apples, do the tomato two-step, or just soak up local flavors right downtown according to the Daley Center events calendar.
Looking for a unique challenge with your Thursday? Reggie Hathorn’s Fragrance Making Class is happening at 1 p.m.—test your sniffer, concoct your own scent, and maybe invent Eau de Deep Dish, as Eventbrite lists in its quirky calendar.
If laughter is your superpower, the United Center is about to host Nate Bargatze’s Big Dumb Eyes World Tour—the man’s got jokes sharper than the wind off Navy Pier. Arrive early to score pre-show party perks and exclusive merch. United Center has details for all you comedy lovers out there.
Now, hot off the Chicagoan press: The city is abuzz with new eats in West Loop—rumor has it, a ramen spot so authentic it’ll have your chopsticks doing a touchdown dance. Transit agencies say Blue Line trains are running on time today, which in itself is a minor miracle worth a cheer.
Still craving adventure after hours? Take the El north to Andersonville for a stroll—it’s all local boutiques, Swedish bakeries, and that sort of indie charm that makes even a seasoned globetrotter like me want to linger. Or go wild and try the Green City Market for autumnal treats downtown; the cider donuts are life-changing, according to Chicago on the Cheap’s event calendar.
Here’s an Oly Bennet fun fact: The iconic Chicago “dibs” tradition—staking claim to a parking spot with offbeat objects—kicks into high gear every time the weather turns. If you see a barstool, lawn chair, or even a flamingo squatting in a snow-cleared spot, it’s sacred territory. Respect the dibs, folks!
Don’t forget, this weekend’s bringing the Pumpkin Party at Gallagher Way, the Boo! at the Zoo bonanza, and Halloween haunts everywhere from Lincoln Park to Wrigleyville. Tomorrow’s episode will feature more tricks, treats, and epic ways to chase the thrills of the world’s quirkiest city.
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