Twinkling Lights, Hot Drinks, and Chicago Swagger - Things to Do in the Windy City this Winter

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennet, coming at you on Friday, December 12, 2025. The city’s in peak winter-holiday mode: cold enough for cozy layers, but perfect for twinkling lights, hot drinks, and maximum Chicago swagger.Here’s the vibe today: downtown is buzzing with shoppers and office parties, the lakefront is brisk but beautiful, and the Loop is glowing with holiday lights and market stalls. Navy Pier’s Winter WonderFest, according to Navy Pier, is in full swing with indoor rides, ice skating, and a 42-foot holiday tree inside Festival Hall, so you can go full winter warrior without freezing your eyelashes off.If you want events, Chicago has stacked the lineup today. Third Coast Review’s Chicago Curated Weekend highlights Winter WonderFest at Navy Pier for family-friendly rides, slides, and a spin on the Centennial Wheel. Over at the Chicago Theatre, My Guide Chicago and Madison Square Garden Entertainment both spotlight Cirque du Soleil’s “’Twas the Night Before” tonight, turning holiday chaos into acrobatics that would impress even the most hardened Bears fan. Third Coast Review also points to the Millennium Park Holiday Sing-Along near Cloud Gate this evening, where you can belt out seasonal songs under the city lights for free. And for nightlife lovers, Lincoln Hall and Schubas are running a full slate of indie shows all weekend, giving you plenty of options to trade your mittens for a drink and live music.Sports twist for you: DePaul University reports that the Blue Demon Holiday Classic track and field meet is happening today at Gately Park. It’s not your typical tourist stop, but if you love competition, watching sprinters and jumpers go all-out indoors is a seriously underrated way to warm up.On the news-and-updates front, holiday transit patterns mean the CTA is running busy but frequent service to hotspots like the Loop, Navy Pier connections, and Wrigleyville’s Winterland and Christkindlmarket, as highlighted by city event roundups and Third Coast Review’s coverage of the Allstate CTA Holiday Train rolling through various lines this season. Expect crowds, but it’s usually faster than driving near Millennium Park or the Magnificent Mile, especially in the evening.Now, Oly’s must-do list for your Chicago day. First, hit Millennium Park: check out the city’s Christmas tree, swing by the Bean, then walk over to the Christkindlmarket at Daley Plaza, which the Daley Center’s calendar calls a traditional German outdoor market with food, ornaments, and mulled wine that could thaw a polar bear. Second, make Navy Pier your afternoon playground with Winter WonderFest, then step outside for a stroll along the pier for skyline views. Third, cap the night either with “’Twas the Night Before” at the Chicago Theatre or a gig at Lincoln Hall or Schubas—two of the city’s most beloved mid-size music venues, as Third Coast Review notes.Local tip time: if you’re bouncing between downtown events, use the Pedway, Chicago’s underground walkway system that links parts of the Loop. It’s not glamorous, but in winter it’s like a secret level in a video game that skips the wind-chill boss. Also, when grabbing food, remember that some of the best bites are just off the main drags—duck a block or two away from Michigan Avenue or Navy Pier for more local spots and shorter lines.Before I sign off, mark your mental calendar: this weekend continues the full holiday blitz—more Winter WonderFest, more Christkindlmarket, Randolph Street’s Holiday Market with over 100 vendors as highlighted by Third Coast Review, plus more Cirque du Soleil performances and concerts around the city. Tune in tomorrow for a fresh rundown of what’s next and where to go.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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