Welcome, brilliant listeners, to Things to Do in Chicago with your adventure-obsessed host, Oly Bennet! Today is Thursday, September 11, 2025, and if you’re feeling the Chicago buzz, you’re not alone. The Windy City is absolutely shimmering with late-summer energy—think breezy lakefront strolls, rooftops packed with Cubs fans reliving last night’s homer, and the sweet scent of street food promising delectable detours. Skies today are mostly clear, so grab your sunglasses—unless you fancy a surprise cameo on the local weather report catching treats from a rogue food truck.

Hold onto your berets and beanies, because tonight’s lineup is a colorful feast for every kind of fun-seeker. If you’re itching to flex your imagination or just roll the world’s most epic perception check, the Broadway Playhouse at Water Tower Place is hosting Dungeons & Dragons: The Twenty-Sided Tavern, a wildly interactive show bringing everyone’s favorite dice-rolling adventure to theatrical life. Insider tip: audience participation could earn you cheers and, let’s face it, serious bragging rights.

If your idea of a quest involves shredded guitar strings and heart-thumping music, Park West is the place to be, featuring the bonkers-talented Marcin. This Polish guitar sensation is bringing his genre-mashing, looping wizardry to Chicago tonight—fans everywhere are already sounding the fretboard alarm.

Looking to keep things family-friendly? Misericordia Family Fest at 6300 N. Ridge Ave is packing the afternoon with live performances, games, and food galore. This annual bash has something for everyone and supports an amazing cause: helping people with developmental disabilities. There’s a raffle, so you might just go home with more than a sugar rush and a balloon animal shaped like Wrigley Field.

And night owls, the Wrigleyville Night Market at Gallagher Way kicks off at 4 PM and keeps the vibes lively into the evening with local vendors, bites, and popup bars—a classic neighborhood market with a Chicago twist and possibly the city’s best people-watching outside a Blackhawks overtime.

For your culture fix, Steppenwolf Theatre is premiering a brand-new show—according to WTTW, it’s one of the week’s absolute must-sees for arts lovers. If shimmering lamps strike your fancy, the city’s also buzzing about a new Tiffany lamp exhibition so detailed it almost counts as mood therapy.

Chicagoans on the move, take note: the Red Line is running on schedule after last week’s track repairs, making it a prime day for hopping between neighborhoods, taco joints, museums, and those magical late-summer rooftop patios.

If you’re plotting the perfect Chicago day, start at the Lincoln Park Zoo (still free!), stroll through the Peggy Notebaert Nature Museum, and snag an espresso at a café tucked beside the lake. For wild photo ops and secret local lore, swing by the hidden garden behind the Art Institute—a peaceful patch away from the buzz, beloved by locals and ducks alike.

Oly’s top traveler tip: Don’t just look up at the skyline—look down! Some of Chicago’s fiercest history is etched into sidewalk plaques scattered along Michigan Avenue, revealing tales of buried rivers, roaring parades, and marathon finish-line miracles the tour guides never tell you about.

Tomorrow’s forecast calls for even more fun, with the opening day of a new street food festival and, rumor has it, a secret jazz set popping up somewhere in Pilsen. Hungry for more quirky tales and untold adventures? Tune in tomorrow, and bring an appetite for the unexpected.

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