Show notes
Welcome back to Things to Do in Chicago, where your favorite globe-trotting sports fanatic brings you the absolute best happenings across this incredible city. I'm your host, Ollie Bennett, and let me tell you, it's Thursday, December 4th, 2025, and Chicago is absolutely buzzing with holiday magic and unbridled festive energy.Today the Windy City is living up to its name with that classic December chill, but don't let that stop you because the holiday spirit is cranked up to eleven. We're talking lights, music, ice skating, and enough seasonal cheer to make even the most cynical sports enthusiast crack a smile, which, spoiler alert, includes me.Let's dive into what's happening right now. First up, if you're feeling musical, Brett Eldredge is bringing his Glow Live tour to the Chicago Theatre tonight at eight PM with special guest Steven Rogers. The doors open at seven, so grab your tickets and prepare for some serious country vibes. Speaking of music, over at Hideout Chicago, things are getting political and fun with Politico's Illinois Playbook Live featuring Shia Kapos and special guest Scott Waguespack starting at six PM. Trust me, there's nothing like mixing politics with great live entertainment.Now here's where it gets seriously cool for the family crowd. Navy Pier is hosting Cheer at the Pier tonight from six to nine PM, and this is a special fundraiser event that includes early access to all Winter WonderFest rides and attractions. For just twenty-five bucks, you get complimentary appetizers, winter cocktails, hot chocolate, holiday cookies, plus carolers and a surprise visit from the Grinch himself. The first three hundred guests get a free Navy Pier holiday ornament, so you'll want to arrive early at five thirty for that grand opening.If you want to catch some live theater and performances, Chicago's cultural scene is absolutely exploding right now with over thirty holiday performances across the city featuring everything from reimagined classics to fresh traditions.Here's my must-do for today: Start your morning by catching the CTA Holiday Train, which is running on the Brown Line through tomorrow. Yes, you read that right—Chicago's legendary 34th annual CTA Holiday Train is making its North Side rounds and you can literally ride festive holiday fun through the city. After that, head to Winter WonderFest at Navy Pier where you can ice skate, ride the iconic Centennial Ferris Wheel which is included with admission, and check out the stunning 42-foot holiday tree inside Festival Hall.Local pro tip that'll make you feel like a true Chicagoan: The Christkindlmarket in Wrigleyville is an absolute gem for authentic European holiday vibes. Grab some mulled wine and handmade ornaments while supporting local artisans. It's not your typical mall experience, and honestly, it's where the real Chicago holiday magic happens.Looking ahead to tomorrow, Friday December 5th, we've got Winter WonderFest continuing, Caroling at the Bean happening from six to seven PM at Cloud Gate, and the Santa Hustle Chicago 5K at Montrose Harbor where you can run in costume and grab hot cocoa afterward.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