Welcome, adventurers, to Things to Do in Chicago! Today’s Friday, October 17, 2025, and Oly Bennet reporting for duty—fueled by deep-dish pizza, Lake Michigan breeze, and an obsession with everything weird, wacky, and wonderful in the Windy City. Let’s catch today’s vibe: the autumn air is crisp, the lakefront is buzzing with Friday-feels, and if you’re lucky, you might even spot locals perfecting the ancient sport of dodging falling leaves on Michigan Avenue.

Chicago’s got its game face on for fall. Festivals pump energy into every neighborhood—even the pigeons seem peppier. What’s setting the tone? According to Patch.com's event calendar, there’s music, movie magic, and family fun splattered all over town, perfect for everyone from culture buffs to sports maniacs and giggle-seekers.

Amping up for tonight, here’s some top-tier Chicago action to launch your weekend:

Comedy takes center stage at The Chicago Theatre, with Morgan Jay charging in for two shows on The Goofy Guy tour—7 and 10 pm. Expect a riot of laughs, maybe even some tunes, and plenty of joyful mayhem. Don’t forget to check your digital tickets and bags—The Chicago Theatre is a stickler, but they’re committed to maximum fun.

Classical and cool collide at the Studebaker Theater where the Camerata Chicago Orchestra presents Peter and the Wolf at 7:30 pm. Perfect for families or anyone craving an epic soundtrack to autumn.

If music with a modern twist is your jam, Epiphany Center for the Arts rolls out the Golden Hour starting at 5 pm (half-priced wine, anyone?), followed by Future Nobodies with Ghost Days and Twin Ion Engine at 8 pm—a doubleheader of dreamy post-punk and nostalgia-fueled indie rock. Arrive early, catch some art, then drift into sonic bliss.

Night owls, rejoice: Rooftop Cinema Club Fulton Market is running a movie marathon—kick things off with Pride & Prejudice at 5 pm, cue up Scream (1996) at 7:55, and round things out with Friday the 13th (1980) at 10:45 pm. Horror, romance, and skyline views.

Sports fans, United Center hosts a classic: Chicago Blackhawks vs. Vancouver Canucks at 7:30 pm. Expect roaring fans, fast ice, and maybe a hot dog duel that would make Joey Chestnut sweat.

For family fun, the Nights of Little Italy at the Albert kicks off at 9 am with a feast of Italian American cuisine—good luck resisting the cannoli—or swing by Sonny Acres Farm’s Fall Festival in West Chicago for pumpkin picking, hayrides, and haunted barns running through October 30.

In the city news blitz, the 61st Chicago International Film Festival is in full swing, lighting up screens across town until October 26. New restaurants pop up like wild mushrooms in River North and Fulton Market, so try a new spot before the crowds discover it. Public transit updates: the CTA is running regular schedules, but the Red Line might be performing its own Olympic event—train leap-frogging—so leave a little early.

Looking for must-do activities? Stroll Millennium Park (the Bean: still the best spot for group selfies and impromptu tourist Olympics), try a kayaking session on the river if you dare, or catch late-night jazz in a tucked-away club. Oly’s explorer tip: sneak into the Art Institute’s Modern Wing after lunch when crowds ease—bonus cultural karma and some of the world’s best people-watching.

Chicago was nearly named "Lake Michigan City"—imagine cheering on the Lake Michigan Bulls! Let that fun fact fuel your party trivia arsenal.

Don’t miss what’s next: tomorrow brings the magical Arts in the Dark Parade on State Street—think glowing floats, larger-than-life puppets, and more sparkle than a disco marathon. Harvest festivals, film screenings, and rooftop revelry are ready to roll, so tune in for all the details and a fresh batch of wild Chicago happenings.

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