Things to Do in Chicago: Beatle Beats, Donut Delights, and Winterland Wonders

Welcome to Things to Do in Chicago! It's Monday, November 24, 2025, and Oly Bennet here, coming at you live from the heart of the Windy City, where the vibe today is brisk, bold, and bursting with energy. Overnight rain left the streets glistening, and at this very moment, Chicago is shaking off the cold with the kind of spunk only this city can muster. As the city gears up for Thanksgiving, the air is buzzing—almost as much as my sense of adventure!So, what's setting the tone in Chicago today? Holiday lights are officially dazzling the skyline, the annual festivities are rolling out, and music legends are hitting the stage. People are donning their warmest layers and revving up for a week packed with sparkle, sound, and scrumptious treats.Hold onto your hats because Chicago’s events calendar is stacked! First up: the city’s very own Beatle, Paul McCartney, is rocking the United Center tonight. If you fancy singing “Hey Jude” with a few thousand closest friends, this is your night! For the cool cats who want some indie flair, the sensational Lola Young is performing at The Salt Shed, promising a soulful, unmistakably London groove right here in Chi-town. If you want some family adventure, the Holiday Express at Blackberry Farm is chugging along, plus you can catch the Winter Flower Show: “Merry & Bright” at Garfield Park Conservatory—it’s basically a living snow globe, minus the frostbite. And if you’re itching to shake a leg, slide into the Chicago Contra Dance happening in the evening, where the city’s historic community halls bring together quick feet and old-school charm. Night owls and jokesters, make a beeline to the Laugh Factory for the Stand Ups Sit Down Comedy Showcase and prepare for side-splitting hilarity!Now for the scoop on what’s new around town! Chicago’s restaurant scene saw another wild twist this week with several hot new openings—from a Japanese fusion eatery in River North to a quirky donut cafe on Southport Avenue with flavors that would make Homer Simpson weep with joy. CTA announced temporary changes to the Red Line—it’s express all week during rush hour due to ongoing renovations. If you're headed downtown, plan an extra minute or two, unless you have roller skates (which I wouldn’t recommend—Chicago drivers love a challenge).Looking for must-do activities today? Don’t miss the legendary Christkindlmarket at Daley Plaza—grab yourself a mug of spiced cider and try not to buy everything in sight. Swing by Gallagher Way, where Winterland is back, complete with outdoor skating, holiday workshops, and enough twinkle to make Rudolph jealous. If you crave something quirky, drop by the Ann Kogen “Street” photo exhibition at Norris University Center, featuring snapshots that capture real Chicago life—Potholes! Pigeons! Tourists blissfully lost!Here’s a local tip: When riding the ‘L’ after a big event, skip the first car—locals know it’s always the most crowded. And if you’re at Navy Pier, hunt down the hidden staircase by the Crystal Gardens for the best skyline selfie in the city. Random fact for today: The deep-dish pizza was born in Chicago in 1943, but did you know the first recipe included anchovies? Now THAT’S a power play!Tempted for tomorrow? Just wait—Durango Fest, a sensory-friendly night at Brookfield Zoo, and the “Wicked” themed light show at Cantigny will all be lighting up the scene. Tune in again for more wild, wonderful, and downright peculiar adventures.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/3V0gjPtFor 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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