Chicago News and Information

Outdoor Adventures, Iconic Sights, and Quirky Finds in the Windy City


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Welcome, listeners, to "Things to Do in Chicago" with Oly Bennet, globe-trotting fanatic for all things quirky, fun, and delightfully unexpected! It’s Thursday, November 6, 2025, and while the Windy City might have a nip in the air, the vibes are as vibrant as a deep dish pizza—steaming, layered, and absolutely irresistible.

Today the fall chill is rolling in, leaves are crunching underfoot, and the city feels like a movie set for every rom-com ever, just with more bean-shaped sculptures and less accidental coffee spills. Chicago bears a real energy boost right now as the last pre-holiday events stack up and people are squeezing in more outdoor adventures before winter wins the showdown.

Let’s jump straight into today’s lineup, and folks, it’s packed tighter than a CTA train at rush hour! Kicking off for music lovers, Hot Water Music is bringing their fiery punk rock to the Byline Bank Aragon Ballroom at 5 PM—get ready for some crowd-surfing and singalongs that’ll warm you up faster than a Lake Michigan polar plunge, as listed by Chicago Theater.

Comedy fans, file this under can’t-miss: tonight at The Chicago Theatre, Ralph Barbosa brings his “Bean Without a Cause Tour” to town. Prepare for a laughter marathon—doors open at 7 PM, so get those tickets ready and your cheeks primed for some serious smiling according to MSG.

Over at Navy Pier, the Chicago Children’s Museum is turning childhood nostalgia into an absolute joy-fest with “Take Care with Peanuts: The Exhibit.” Transport yourself into Charles M. Schulz’s world—test your piano skills with Schroeder, try Lucy’s advice booth, or join Snoopy on an epic adventure. It’s interactive, heartwarming, and perfect for families of all ages, running through January as announced by Navy Pier.

For those with a love of discovering the city itself, guided architecture tours at the Chicago Cultural Center are in full swing, offering glimpses into wild art installations and architectural quirks—there are still slots for today, highlighted by Chicago on the Cheap.

And if your idea of nightlife blends ice skating and stunning city views, head over to Maggie Daley Park for the outdoor skating ribbon, where experts and first-timers alike glide beneath the skyline lights. The ribbon is open, the cocoa is hot, and the selfies—let’s face it—are pure gold.

In local news worth chatting about over a loaded hot dog (yes, no ketchup debate today): look out for traffic delays around the Loop, thanks to set-up for the Christkindlmarket at Daley Plaza. It’s one of Chicago’s biggest holiday traditions, so even if you spot construction, think of it as a sneak peek at cheerful chaos to come, as reported by Daley Center. On the food front, rumor has it a new vegan bakery just opened in Wicker Park—look for the green awning and the line of hipsters trying to decide if croissants taste better with oat or almond milk.

Public transit remains your friend today: CTA updates say everything is running smoothly, so save money and skip the hunt for parking—unless you’re competing in your own private “Circling the Block Grand Prix.”

Must-do activities today? Embrace the season with a walk through Millennium Park—snap a photo at Cloud Gate, then duck inside the Art Institute to thaw out beside Monet’s haystacks. Or, if you like treasures that fly under the radar, stop by the International Museum of Surgical Science for exhibits that are both spooky and fascinating—imagine a haunted house for the brainy crowd.

Sporty tip from yours truly: if you’re feeling intrepid and want to channel peak Chicago energy, challenge a friend to the stairs at Swallow Cliff Woods out near Palos Park. Your legs will burn, the view is epic, and you’ll have an excuse to reward yourself with a multi-pound Italian beef later.

Fun fact to wow your friends: The Chicago River is the only river in the world that flows backward, thanks to an engineering flip-flop in 1900—proof that this city doesn’t just roll with the punches, it throws them right back.

Don’t close your calendar yet—tomorrow brings Druski’s outrageous “Coulda Fest” at the United Center, and for the culture vultures, the Chicago Architecture Biennial continues with new installations.

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.

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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
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Chicago News and InformationBy Inception Point Ai