Welcome, listeners, to “Things to do in Chicago!” Today is Friday, September 19, 2025, and I’m your host, Oly Bennet—the only sports nut who knows more about competitive cheese-rolling than football. But don’t worry, I’m also here for the art, music, and that legendary Chicago pizza (trust me, deep dish is basically an endurance event). The city’s in its autumn groove—there’s a crispness in the air, a gentle breeze off Lake Michigan, and everyone’s swapping summer shades for team scarves. The sun’s breaking through, making this Friday absolutely perfect for some adventures.What’s the vibe? High-energy and eclectic! There’s a creative buzz thanks to the third annual Chicago Exhibition Weekend, spotlighting 50 dazzling galleries and spaces across the city. According to Choose Chicago, this rolling art extravaganza means every neighborhood is bursting with installations and artistic happenings from now until Sunday. If you’re the festival type, make your way to the Inaugural Old Town Oktoberfest at 1360 N Wells Street, opening tonight and pouring frothy German brews and good vibes all weekend long, per Chicago Patch. If beats are more your style, Hamilton Park is home to the 26th Annual Englewood Jazz Festival, where Chicago’s jazz roots will keep you grooving all day, according to Live the Spirit Residency.Film buffs, you’re about to enter cinematic heaven with Reeling: The Chicago LGBTQ+ International Film Festival and the Underground Film Festival rolling out the red carpet through September 28. Landmark’s Century Centre Cinema and additional venues across the city will be buzzing with the latest in queer and experimental cinema. Feeling feisty? Riot Fest kicks off in Douglass Park with Green Day, Blink-182, and yes—Weird Al, because nothing says Chicago like a polka-fueled mosh pit! That’s your ticket to punk, hip-hop, and everything in between until Sunday.For families, the Messi Experience is now open at 2367 W Logan Blvd—part high-tech museum, part football fantasy camp—where you can dribble virtually with Lionel Messi. Over in Lincoln Park, tonight isn’t just perfect for a stroll—it’s also '80s vs. '90s Night at the Zoo, because nothing brings generations together like moonwalking with a llama.Turning to local news, foodies have reason to celebrate with acclaimed chef Lucia Martinez’s new tapas spot, Olea, officially open in River North. Public transit is running with increased Red and Blue Line service this weekend, making all these events extra accessible. And an important heads-up: The city’s rolling out new protected bike lanes on Milwaukee Ave, so cyclists rejoice and Uber drivers, try not to panic.Now, for must-do activities—start your day gawking at public art in Millennium Park, then hit the Chicago Riverwalk for lunch (don’t skip the vendors whipping up the city’s best hot dogs). Got curious kids? The Museum of Illusions recently reopened on East Washington Street with over 20 new mind-bending exhibits, as reported by Secret Chicago. If you want to feel like a local, skip the big souvenir shops and pop into one of the city’s legendary thrift stores—there are secret treasures in every corner, especially in Wicker Park.Here’s your Oly Bennet tip of the day: If you want a true taste of neighborhood Chicago, hop on a Divvy bike and cruise along the Lakefront Trail just as the sun sets. Legend (and last Tuesday’s traffic report) says it’s the fastest way to fall in love with the city and maybe even outrun a Segway tour.Stick around for Saturday and Sunday because tomorrow promises acrobats, pop-up beer gardens, and the Navy Pier’s 4th annual Chicago Live! festival jam-packed with over 100 acts. And I’ve got a hot tip for the food-obsessed: Chicago’s Jerk, Seafood & Vegan Festival fires up this weekend in Washington Park, blending smoky flavors with live music and a joyous crowd.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

Ask this episode

“What did the council decide on item 42?” — answered with the speaker and the moment.

Transcript

Related