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Chicago Winter Wonderland: Cirque, Wrigley, and Holiday Cheer

11 Dec 2025

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Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut buddy, Oly Bennet. Chicago is buzzing today with classic winter-in-the-city energy: chilly temps, big coat weather, and that perfect excuse to power-walk like you’re in your own sports montage along the lakefront.Let’s kick off with today’s vibe-setters. Over at The Chicago Theatre, Cirque du Soleil brings holiday acrobat chaos in the best way with “’Twas the Night Before…” tonight at 7 p.m., turning State Street into a festive circus playground, according to Madison Square Garden Entertainment. Up in Wrigleyville, Winterland at Gallagher Way is in full swing, with ice skating, holiday lights, and rides inside Wrigley Field itself, as Gallagher Way’s event schedule highlights. It’s like someone turned a ballpark into a snow globe…and then added hot chocolate and beer.For live music fans, the Hideout’s ultra-intimate stage hosts “Andrew Sa’s Lonesome Holiday” tonight at 7:30 p.m., and the venue reports the show is already sold out, which tells you the holiday crooning game is strong. Art lovers can head to the Driehaus Museum this evening for “Thursday’s Holiday Spirits: A Collection of Victorian Yuletide Ghost Stories” from 6 to 8 p.m., listed on Chicago Gallery News, mixing spooky vibes with Gilded Age glamour. And for a more reflective moment on Michigan Avenue, the Magnificent Mile calendar notes a Peace Concert at Fourth Presbyterian Church, pairing poetry from the Poetry Foundation with new music in a serene chapel right off the shopping chaos.On the news-and-updates front, Newcity recently highlighted that the Obama Presidential Center has opened a public hoops court, adding a fresh, very-Chicago spin to Jackson Park. That means you can literally go shoot around on a court inspired by the city’s most famous basketball-loving president—streetball meets history lesson. Newcity also reports that Gibsons is coming to Fulton Market, turning that already food-obsessed neighborhood into even more of a culinary power play, so keep that area on your steak-and-cocktails scouting report.If you’re plotting your day, here are some Oly-approved plays. Hit Navy Pier and the Chicago Children’s Museum for family fun—hands-on exhibits and space for kids to run wild, as the museum’s own visit page describes. Swing north to Gallagher Way for skating and winter festivities, then warm up with a classic deep-dish showdown in Lakeview. Culture fans can double up with an afternoon gallery stop and an evening at the Driehaus ghost-story event, then cap it all off with cocktails in River North.Local tip for you: Chicagoans treat the CTA like a pro sports strategy. Get a Ventra card, stand to the right on escalators, and when a bus or train door opens—move with purpose. Also, if the wind is howling, use the Pedway downtown, that underground walkway web connecting buildings, to cut your exposure time to “human popsicle” levels.Before I sprint off to my next weird sporting event: tomorrow brings more holiday concerts, museum happenings, and neighborhood light displays across the city, plus weekend ramp-up energy in Wrigleyville and Fulton Market. Tune in next time as we scout the best picks so your Chicago days stay at championship level.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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