Chicago's Winter Wonderland: Festive Chaos, Cirque du Soleil, and Vintage Finds

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennet, coming to you on Saturday, December 13, 2025. The city’s in full winter-showoff mode: cold, crisp lakefront air, holiday lights everywhere, and just enough wind to make you question your life choices if you forgot a hat.Today’s vibe? Pure festive chaos. Navy Pier’s Winter WonderFest is in full swing with indoor rides, an ice rink, and a ticket that even includes a spin on the Centennial Wheel, turning Festival Hall into a giant snow globe of screaming kids and secretly-thrilled adults, according to Navy Pier’s event listing. Over in the West Loop, the Randolph Street Holiday Market is back at Plumbers Union Hall, serving vintage treasures, holiday décor, seasonal cocktails, DJs, and a full-on “mecca of cool” shopping party, as described by Randolph Street Market organizers.For families, the Chicago Waldorf School Holiday Fair in Andersonville runs from 10 a.m. to 3 p.m. at 5200 N Ashland, featuring local vendors, food, and kid-friendly activities, open to the whole community, according to the school’s event page. If you want something big, bold, and acrobatic, The Chicago Theatre is hosting three performances of “’Twas the Night Before…” by Cirque du Soleil today at 1, 4, and 7 p.m., bringing high-flying holiday storytelling downtown, per The Chicago Theatre and MSG event listings. And for you night owls, Hideout Chicago is throwing a DJ Night with Plastic Crimewave & Sara Gossett at 8 p.m., a 21+ hang with deep cuts and indie vibes, according to The Hideout’s calendar.On the newsy side of things, Newcity reports Chicago’s creative scene is buzzing, with new design spaces forming on West Hubbard and fresh gallery action planned in West Town, further cementing the city’s rep as an arts-and-design playground. Add that to ongoing cultural worker organizing at local museums and planetariums, as noted by the Chicago Sun-Times via Newcity, and you’ve got a city where even your favorite exhibits have union roots.Must-do ideas for today: start with a brisk stroll through Millennium Park to see the holiday lights and the ice rink, then warm up with hot chocolate in the Loop before heading to Randolph Street Holiday Market to hunt for the weirdest, most wonderful vintage ornament you can find. Swing by Navy Pier’s Winter WonderFest if you’ve got kids—or if you just love rides and pretending you’re not slightly dizzy. Cap the night with Cirque du Soleil or that DJ set at the Hideout for maximum story-worthy content.Local tip from your sports-obsessed explorer: if you’re hopping between neighborhoods, use the Red Line as your main artery—Andersonville via Berwyn, the Loop via Lake, and easy transfers to hit Wrigleyville or the West Loop. And when crossing streets in winter, watch out for what locals lovingly call “Chicago ankle-deep mystery slush.” Never trust a shiny puddle.Stay tuned, listeners—tomorrow brings even more holiday markets, winter pop-ups, and neighborhood bar shenanigans, plus we’ll scout any quirky sports or offbeat competitions happening around town. You won’t want to miss it.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

There are no comments yet.

Please log in to write the first comment.