Welcome to Things to Do in Chicago, brought to you by Oly Bennet, your globe-trotting sports nut on the prowl for the city’s quirkiest happenings! It’s Saturday, September 20, 2025—grab your Cubs cap or your Picasso-print umbrella, because Chicago today is a delightful mashup of end-of-summer buzz and fall festival flair. The weather’s mild, sunny with a fun-loving breeze zipping off Lake Michigan—perfect for that just-right blend of shorts-and-light-jacket maneuvering. The city’s streets are alive with laughter, music, and a vibrant art scene pulsing through every neighborhood.

Feeling artsy? The third annual Chicago Exhibition Weekend rolls into its second day, transforming the city into a living gallery with 50 pop-up exhibitions sprawling from Pilsen to Uptown. Expect dazzling installations, surprise performances, and local artists so avant-garde, you’ll swear their paintbrushes attended improv classes with Second City. Choose Chicago says this is the place to soak up that creative spirit and maybe score a selfie with something abstract.

Jazz lovers, it’s your moment! Hamilton Park hosts the final day of the Englewood Jazz Festival, spotlighting the 60th anniversary of Chicago’s own Association for the Advancement of Creative Musicians. Ernest Dawkins leads the charge, unleashing wild sax riffs and the relentless beat of jazz that’s experimental and soulful—bring a picnic blanket and join the musical movement that made Chicago the unofficial jazzy planet in the solar system.

Soccer fanatics and family adventurers can sprint to Logan Square for The Messi Experience, an immersive soccer extravaganza dedicated to Lionel Messi. Imagine interactive exhibits mixed with the sneakerhead energy of ESPN meets Messi’s magic—plus exclusive murals from local graffiti wizard Kane One. Snap a photo with the Messi mural and debate with your crew: was Messi’s left foot ordained by the soccer gods, or is he just allergic to walking?

If you want more festival fever, swing by Old Town Oktoberfest and raise a stein in Chicago’s first German neighborhood. There’s bratwurst, oompah bands, and a dance floor just daring you to invent a new move called the “Loop Line Shuffle.” If you can still walk straight afterward, make tracks to the Summer’s Last Dance Music & Arts Festival in the southwest, where DJs spin, artists paint, and every food truck battles for your undying burger loyalty.

For those seeking high culture, the Museum of Contemporary Art is running Chicago Performs—a wild showcase of live contemporary dance, shadow puppetry, and communal rituals. Helen Lee’s movement exhibit even includes sound bowl workshops and guided walks to the lake, proving Chicago’s not just about deep dish; it’s about deep feels.

Now, for fresh scoops: Small business lovers can mingle at today’s Chicago Small Business Expo in Lincoln Park. Watch for Boba Break’s grand opening on Clark Street—it’s rumored the bubble tea is so good, it’ll have you humming “Sweet Home Chicago” after every sip. The CTA reminds everyone that red line service downtown now runs every 6 minutes—so hop on and get exploring.

Must-do tip from Oly: If you want a true Chicago memory, grab a Divvy bike and ride along the Lakefront Trail at sunset. You’ll get jaw-dropping skyline views, waterfront breeze, and possibly a goose photobomb. Locals know this is Chicago’s free roller coaster, minus the fear of dropping your hot dog.

Fun fact to impress your friends: The city invented the Ferris Wheel for the 1893 World’s Fair. That’s right—next time you see Navy Pier’s wheel, thank Chicago for putting a spin on history!

Feeling hungry for more? Tomorrow, watch out for Czech Heritage Week events and another round of wild art at Chicago Exhibition Weekend. Don’t miss our next episode—Oly Bennet will dig up more sparkling sports, sideshows, and festival shenanigans.

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