Show notes
Welcome, listeners, to Things to Do in Chicago with your resident globe-trotting, sports-loving, deep-dish devourer, Oly Bennet! It's Friday, October 3, 2025, and Chicago’s rolling into October with a jolt of high-energy goodness—think pumpkin spice but with more attitude. The air is crisp, the leaves are flirting with full-on gold, and the city’s electric with a lineup of events wild enough to impress even a jaded marathon runner.Today’s weather? Brisk but brilliant—perfect for grabbing a sweater and stomping out into the action, whether your vibe is art, music, or chasing down the city’s quirkiest fun with friends and family.Let’s talk about what’s popping today. First up, wine lovers, it’s your time to shine! The Lincoln Park Wine Fest is uncorking bottles and pouring tastes at Jonquil Park tonight starting at 5pm—expect top-drawer wines, food pairings, and a little sommelier wisdom sprinkled in, all for a good cause.If you’re into art (and who isn’t, after seeing Chicago’s skyline?), the West Town Art Walk is on tonight from 5 to 8pm along Chicago Avenue. This isn’t just an art stroll—it’s a full-on creative bash with over 40 neighborhood businesses transforming into art galleries, performance spaces, and live music venues. It’s like a pub crawl but with paintings, percussion, and probably a stray ukulele or two.Music junkies, the World Music Festival Chicago is in full swing, filling venues across the city with sounds from every continent. It’s free, it’s global, and you could literally go from Afrobeat to Andean pipes without leaving town. Up for a concert? Pool Kids and Truth Club hit Lincoln Hall’s stage tonight, and for a dose of classical flair, the Rembrandt Chamber Musicians are tackling Beethoven at 7pm—it’s highbrow with a side of toe-tapping.Got little monsters? Check out the Rooftop Cinema Club in Fulton Market screening The Addams Family at 5pm—a ghoulishly good time for families. Or, for those after a retro groove, Chicago’s Southland is hosting Disco Circus at Gaelic Park, proving once and for all that bell-bottoms truly never die.As night falls, Taylor Swift fans get spoiled with a “Life of a Showgirl” album bash at Pippin’s Tavern and another late-night party atop the Rooftop Cinema Club. Meanwhile, theater buffs, don’t miss The Infinite Wrench at Neo-Futurist Theater—a mad dash of 30 mini-plays squeezed into an hour. Pure creative adrenaline.In today’s local news, foodies and carb connoisseurs can rejoice—today’s the grand opening of the Auntie Anne’s and Cinnabon co-branded flagship on Michigan Ave. That’s right: the dream team of pretzels and buns has hit the Magnificent Mile, so prep your taste buds.Transit-wise, word on the street is CTA Red Line trains are running without major delays today—miracles do happen. For public art fans, the city is rolling out more interactive murals in Logan Square, so bring your camera and snap some new profile pics.Must-do activities? Stroll Millennium Park’s gardens, check out the immersive digital exhibits at WNDR Museum, or duck into Garfield Park Conservatory for a splash of tropical warmth. For a quieter, hidden gem, try the art-and-toy mashup at Rotofugi—guaranteed to delight your inner kid (or very real kid).Want to blend in like a local? Skip the deep-dish queues and duck into a tavern for a Chicago handshake—a shot of malört and a cheap beer. It’s an... acquired taste, but hey, you only live once.Looking ahead to tomorrow, there’s the Lincoln Square Ravenswood Apple Fest, BOO at the Zoo at Brookfield, and the South Side Science Festival—all ripe for adventure. Tune in for more wild and weird happenings. Until then, keep exploring, keep laughing, and keep Chicago weird.Thanks for listening, please subscribe, and remember—this episode was brought to you by Quiet Please podcast networks. For more content like this, please go to Quiet Please dot Ai.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI