Welcome, fabulous listeners, to Things to Do in Chicago! It’s Friday, November 7, 2025, and I’m your globe-hopping, high-fiving host, Ollie Bennet—ready to launch you into Chicago’s whirlwind of sights, sounds, and shenanigans. Let’s lace up those metaphorical sneakers, because this city never sits still!

First things first: Chicago’s serving up classic November flair—a crisp, invigorating breeze off the lake, perfect for layering up and showing off your best autumn style. Skies today are a cinematic mix of sun and clouds, so whether your plans are street parading or museum marathoning, the Windy City is primed for adventure. The city’s energy? Electric! The holiday sparkle begins to flicker in shop windows, and you can practically smell the hot pretzels on Michigan Avenue.

Now onto the action—what’s popping off today that you absolutely can’t miss? For the culture crusaders, the legendary Black Harvest Film Festival is animating the Gene Siskel Film Center with stories by Black filmmakers, diving deep into the richness of the Black experience. Expect everything from dazzling shorts to powerful documentaries, with special nods to Chicago’s own creative talent.

Music lovers, get ready! Jo Koy is storming the stage at United Center with his Just Being Koy Tour. Known for his sidesplitting stand-up and uncanny ability to turn family quirks into comedic gold, Jo Koy promises belly laughs by the bucketload tonight.

Swing over to Oak Park if your taste buds are tingling. There’s a free tasting event featuring Japan's No. 1 Dumpling popping up, so bring your appetite and your curiosity. Fans of jaw-dropping artistry can catch the ongoing Day of the Dead Quilts Workshop at the National Museum of Mexican Art—immerse yourself in color, texture, and tradition as local artists share the stories of the season.

Looking for giggles with a dash of the bizarre? Head to the Neo-Futurists’ The Infinite Wrench, a turbo-charged theater spectacle where they attempt to cram 30 mini-plays into 60 minutes. Think of it as speed dating for your attention span—no two nights are the same, and surprises are guaranteed.

Families, have no fear—fun runs rampant! The LEGO Group’s Holiday Lane at Water Tower Place is stacking up holiday joy, while kids can channel their inner artists at Fall Art Camp in Riverside. For movie buffs who love nostalgia with their popcorn, ChiTown Movies in Pilsen is spinning drive-in magic all weekend.

Let’s pivot to the latest Chicago buzz. The Old Town Pour House in Oak Brook has dropped a fresh Chef Selects menu, guaranteed to delight foodies. If you’re tackling the city by L—the Red Line’s just had a slick new update, which means smoother rides ahead for transit warriors. And, if you’re hunting for a new haunt to fill your belly, rumor has it there’s a ramen spot opening soon near Wrigleyville—keep your chopsticks at the ready.

If time’s tight and you want maximum Chicago in minimum moments, hit Millennium Park to admire the shifting autumn colors reflected in Cloud Gate. For a local favorite, stroll the Chicago Riverwalk, where street performers crank up the pulse and the iced lattes flow even as the leaves fall. Fancy feeling like a true Chicagoan? Order your hot dog “dragged through the garden”—translation: loaded with all the classic toppings, but never ketchup!

Here’s your Ollie Bennet fun fact: Chicago’s downtown is built on layers, literally—a street-level sandwich where you can walk above, below, or sometimes through history. There’s a secret network of tunnels and lower streets used for deliveries and, if you believe the legends, once for a few sneaky Prohibition-era getaways.

And before you dash off, a quick teaser: Tomorrow’s calendar is stacked with holiday markets, tree lightings, and perhaps an appearance by someone in a red suit with a beard—you know, for those already humming Jingle Bells. Join me...