Welcome, thrill-seekers and adventure-lovers, to Things to do in Chicago! It’s Thursday, September 18, 2025, and Oly Bennet here, your jetsetting mischief-maker on a quest to uncover the quirkiest, coolest, and wildest happenings in the Windy City. The streets are buzzing, leaves are hinting at autumn, and today we’ve got sunshine with just enough of that classic Chicago breeze to keep you on your toes.

Let’s set the scene: the city is alive with legendary music, global art, family festivities—and a little K-Pop magic thrown in for good measure. Whether you’re a jazz hound, an art aficionado, or just looking for a new spot to graze, Chicago’s your playground.

First up, jazz fans, unite! The historic Englewood Jazz Festival kicks off today at Hamilton Park, grooving its way to a whopping 26th year, and celebrating the 60th anniversary of the iconic Association for the Advancement of Creative Musicians. Expect cutting-edge performances, community spirit, and enough funky rhythms to get even the pigeons dancing—this fest runs through Saturday and it’s totally free.

If you fancy global vibes and some big hair flips, the Athenaeum Center transforms tonight for the VIVIZ World Tour—K-Pop superstar trio bringing their New Legacy show to town. Prepare for synchronized moves, glowing light sticks, and a crowd louder than the L train in rush hour.

Art explorers, prepare your eyes for a feast! Columbia College is hosting the Filter Photo Festival, and Millennium Park is home to two monumental Franz West installations—think wild colors and massive sculptures that’ll make you feel like you’re starring in your own surreal adventure flick.

Families, gather the cubs! The Chicago Children’s Museum at Navy Pier has just launched their Take Care with Peanuts exhibit. Kids can step straight into the world of Charlie Brown, meet the gang, play alongside Schroeder, and channel their inner Lucy at the shrink booth. Bonus: Explore the Division Street Farmers Market this morning for sweet cider, crunchy apples, and more local treats than you can carry.

If you’re craving fresh air and a change of perspective, I’m all about the Chicago Skyline Sail from Navy Pier—catch breathtaking city views from the water, perfect for those epic selfies your friends will never top.

Now for some delicious news: Navy Pier has just rolled out a new roster of fall and winter events, from the massive Chicago Live arts festival this weekend to pop-up food fests and fireworks. And don’t miss out—legendary Music Box Theatre just installed a booming new sound system, so movie nights are about to get even more electric, according to Newcity.

Transit tip: CTA’s running smoothly today, but if you’re living that two-wheeled life, Divvy bikes are back in full force and docked at pretty much every corner. Roll like a local and avoid that gnarly Lakeshore Drive traffic jam.

Oly’s fun fact for the day: Chicago’s skyline was shaped by an epic battle—between two rival architects who tried to outdo each other with taller and wackier designs. Stare up, and you’ll see a city literally built on friendly competition.

Can’t get enough? Tune in tomorrow for details on Chicago Exhibition Weekend—over 50 pop-up galleries citywide, and Navy Pier’s jaw-dropping Saturday fireworks. Set your reminders, because this city never, ever runs out of epic things to do.

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