Welcome, listeners, to Things to Do in Chicago! I’m Oly Bennett, your globe-trotting sports nut turned Windy City hype man, coming to you on this crisp December Sunday with Chicago buzzing in full holiday mode. The lakefront air is cold and sharp, perfect for scarves, hot chocolate, and pretending your power walk down Michigan Avenue qualifies as a winter sport.Today the city is a mash-up of cozy, sparkly, and downright rowdy. Over at United Center, the Chicago Bulls take on the Golden State Warriors tonight, turning the West Side into a slam-dunk circus of noise and nachos. The Chicago Theatre is getting festive too, hosting The Jinkx & DeLa Holiday Show this evening, serving drag, comedy, and holiday chaos in one glorious snow globe of glitter. House of Blues is in on the fun with a Sister Hazel brunch show, mixing live music with your eggs like only Chicago can.If you’re in full holiday spirit mode, Christkindlmarket is your mission. The market’s Culture and Cheer Tours today walk you through German holiday traditions, the story behind those iconic mugs, and how to snack your way across the plaza without spilling your glühwein. At Gallagher Way in Wrigleyville, Winterland is in action with ice skating, rides, and family fun in the shadow of the Cubs’ home turf—because even in winter, Chicago finds a way to turn a ballpark into a playground. And dog lovers, Bucktown’s The Dog Stop is hosting Santa and Sleighs, where pups pose with Santa, which is basically the Olympics of adorable.On the news-and-updates front, CTA and Metra are running expanded holiday and event schedules around big downtown happenings and United Center games, so load up your transit card and dress in layers—you’ll thank me when that platform wind hits. Around the city, new restaurant and bar pop-ups are leaning hard into seasonal menus: think hot toddy bars, festive rooftops with fire pits, and comfort food joints perfect for warming up after a loop around Millennium Park or the Riverwalk.If you’re planning your day, here’s the Oly action playbook: start with a late-morning wander through Millennium Park to see the Bean and the city skyline shining in winter light, then swing by Christkindlmarket for snacks and souvenirs. Take the family to Winterland at Gallagher Way for skating and rides, then cap the night with either the Bulls–Warriors showdown, the holiday drag extravaganza at the Chicago Theatre, or live music and drinks at House of Blues.Local tip: Chicago blocks are long—locals think in transit lines, not just distance. If someone tells you “it’s right off the Red Line,” that’s your green light. Also, if the wind’s howling off the lake, walk on the west side of north–south streets; buildings make a surprisingly good defensive line.Tomorrow, look out for more holiday performances, ongoing light shows, and weekday-friendly events as Chicago settles into its workweek-with-a-side-of-magic rhythm. Tune in again for your next game plan so you can hit the city like a seasoned local, not a confused rookie.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

Ask this episode

“What did the council decide on item 42?” — answered with the speaker and the moment.

Transcript

Related