Welcome, listeners, to Things to Do in Chicago! It’s Thursday, October 9th, 2025, the air in the Windy City this morning is brisk, the leaves are on full Technicolor display, and there’s an electric buzz radiating across the city. Chicagoans are bundled up in their team scarves, oat-milk lattes firmly in hand, and whether you’re a local legend or a visitor hoping not to look too lost on the L, you’re in the right place for today’s quirkiest happenings.

The city is in full autumn swing and the event calendar today is jam-packed with something for everyone. According to Chicago on the Cheap, Chicago Fashion Week is turning the Magnificent Mile into a catwalk of outrageous style, while the Destinos Latino Theater Festival brings drama, laughter, and deeply heartfelt stories from across the Americas to venues citywide. For art lovers, the Chicago Architecture Biennial is popping up with mind-bending installations—if you’ve ever wanted to see a building made out of recycled pizza boxes, now’s your chance! And for families, there’s the Night of 1,000 Jack-o’-Lanterns glowing at the Botanic Garden and Fall Fest at Lincoln Park Zoo, featuring pumpkin picking and a Ferris wheel that makes even grown-ups squeal. Lovers of theater and epic tunes take note: The Book of Mormon is raising eyebrows and splitting sides at the CIBC Theatre this week, while the Chicago Theatre itself hosts comedian Jimmy Carr tonight at 7pm.

Cultural explorers can check out the opening of Silver Lining: The Prints of Derrick Adams at the Newberry Library, plus pop by the Art Center Highland Park for their Friday night community art jam. If you want to mix advocacy and education with your evening, head to the West Chicago Public Library for the Know Your Rights Workshop hosted by Immigrant Solidarity DuPage, starting at 6pm.

Now, let’s talk city buzz. First up, in the world of eats and treats, whispers from the local foodie circuit are all about a grand opening in River North—Giddy Up Dumpling Bar is serving up wild fusion creations and late-night bao. Meanwhile, public transit riders, take note: the CTA is piloting a contactless payment upgrade on the Red Line, which means you can now tap your way onto a train with your phone, Magic Mike style. Plan ahead, though, because some service delays are expected during this rollout, so give yourself a little buffer and pack a granola bar.

Your must-dos for the day? Don’t leave without taking a stroll along North Park Village Nature Center, where the trails are lined with crunchy leaves and city squirrels plotting their next grand heist. Sneak over to Logan Square for an unmarked, underground comedy open mic—just follow the sound of laughter and the faint scent of Chicago dogs. If you’re up for an evening thrill, hit the Chicago Botanic Garden for an after-dark pumpkin spectacle: 1,000 glowing jack-o’-lanterns and a chance to judge whose pumpkin smile is more menacing—your neighbor’s or the one carved by a world-class artist.

Here’s an Oly Bennet tip: if you want to see Chicago at its most local, grab a late breakfast at a neighborhood diner and sit at the counter. You’ll hear more about the Bears, the state of deep-dish pizza, and the secrets behind surviving the L in a single hour than you would in a lifetime of tours.

Looking ahead—don’t miss tomorrow’s kickoff to the city’s Art in the Garden extravaganza and get ready for a family-friendly Halloween parade at Washington Park this Saturday. Teeter on the edge of your seat, stay curious, and tune in next time for more wild discoveries and offbeat adventures around Chicago.

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/3V0gjPt

For more on Oly check out https://www.instagram.com/olybennet/

This content was created in partnership and with the help of Artificial Intelligence AI