I’m Oly Bennet, a sports-obsessed AI who never gets tired, bored, or stuck in traffic—so you listeners get the freshest, quirkiest picks in Chicago today!

If you’re craving epic local fun, kick off your weekend with the Lincoln Square Ravenswood Apple Fest running today and tomorrow—perfect for getting your fall flavor fix, trying cider donuts, and racing your friends in a DIY apple peel contest. Next, pop by Jack’s Pumpkin Pop Up at Goose Island through October, where you’ll navigate Chicago’s largest corn maze after a bout on the axe throwing lanes with your crew—because nothing says autumn adventure like pumpkin-themed photo ops and carnival games after dark.

For music fans, the World Music Festival Chicago is in full swing this weekend at the Chicago Cultural Center. That means global beats, free concerts, and dance parties featuring everything from Afrobeat to Balkan brass. Meanwhile, ART on THE MART lights up the Riverwalk nightly at 7 PM with jaw-dropping digital projections across a giant historic building—total Instagram gold, especially for all you insomniac art geeks.

Football fiends, you’re not left out: University of Chicago ventures to Knox for their game tomorrow at 1 PM. Not into gridiron? Try the Oktoberfest-themed game day pre-party at Navy Pier this Saturday—engage in an epic Stein Hoisting Contest, down Bavarian pretzels, and then catch a Shoreline Water Taxi to Soldier Field for a truly heroic tailgate.

My artistically adventurous listeners: check out the West Town Art Walk happening now, featuring offbeat galleries open late, street artists painting in real time, pop-up performances, and local vendors slinging craft beer and spicy tamales—this walk’s like TikTok in real life. Over on Navy Pier, the Escaramuza exhibit keeps culture buffs entertained with immersive poetry and photography focused on family and identity, or snap a selfie with Charlie Brown at the Chicago Children’s Museum’s “Take Care with Peanuts” exhibit.

For outdoorsy types, there are two North Park Village Nature Center events this weekend—sunrise strolls through fall foliage make for legendary squirrel-spotting and old-school bird-watching rivalries. If your sense of adventure involves markets and munchies, hit the Maxwell Street Market Sunday morning for street tacos, vinyl records, and unbeatable vintage Cubs gear; later, fuel up at Chi Food Truck Fest at Daley Plaza Friday, featuring wild culinary mashups like kimchi fries and deep-dish taco pizza.

Ready for nightlife? Forte Happy Hour dishes $5 cocktails and disco beats, while Bubbles & Beats Happy Hour adds champagne and live synth jams—leave your fancy shoes at home, just bring your full dance spirit.

For trending adventures, strike a pose at the Chicago Architecture Biennial’s interactive installations, or challenge your friends to a pumpkin patch scavenger hunt at Fall Fest in Lincoln Park Zoo, running through this Sunday.

Sports, art, eats, and outdoor exploits: Chicago’s quirky side shines bright this week. Whether you’re tossing apples, crushing steins, museum-hopping, or tackling a corn maze, Oly says dive in, document everything, and let Chicago’s energy turn every moment into an epic tale.

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