Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennett, coming to you on Friday, December 19, 2025. Chicago’s in peak winter wonderland mode right now: cold, crisp, and perfect for bundling up, grabbing a hot chocolate, and pretending you’re in your own holiday movie montage along the lakefront.

Let’s lock in today’s vibe. Holiday season is in full sprint, the Loop is glowing, and neighborhoods are twinkling with lights. Over at the Chicago Theatre, Cirque du Soleil’s “’Twas the Night Before…” is back tonight, dazzling State Street with acrobatics and festive chaos, according to Madison Square Garden’s event listings. If you like your Christmas spirit with flips and flying humans, that’s your move.

For high-culture holiday magic, the Joffrey Ballet’s “The Nutcracker” is lighting up the Lyric Opera House with its Chicago World’s Fair–inspired staging, as Chicago Theater’s December schedule notes. Over in Millennium Park, the city’s holiday sing-alongs and skating by the bean keep the family crowd buzzing, while Brookfield Zoo’s Holiday Magic and Lincoln Park Zoo’s ZooLights turn animal watching into a full-on light show, as regional event roundups like Barrington Hills Observer detail.

Tonight’s nightlife? House and techno fans, Chicago’s going big: elrow’s Delusionville takes over Radius Chicago from 8 p.m. till late, promising wild costumes, immersive sets, and enough confetti to re-surface the United Center, per elrow’s official event page. If you prefer intimate and artsy, The Hideout is hosting Andrew Sa’s Lonesome Holiday show this evening, as listed on Hideout Chicago’s calendar—expect cozy vibes, great music, and the kind of crowd that knows all the bartenders by name. And for a rich cultural hit, Old Town School of Folk Music hosts Mariachi Herencia de México’s holiday show tonight, blending mariachi traditions with seasonal classics, according to Old Town School’s concert listing.

On the news-and-life-in-the-city front, December always means crowded trains and buses, so budget a little extra time on the CTA and Metra, especially if you’re heading downtown for those marquee shows. Holiday pop-up bars are in full swing across River North, West Loop, and Wicker Park, with new themed spots pouring over-the-top cocktails in rooms that look like Santa exploded in a speakeasy.

If you’re plotting your perfect Chicago day, here’s the Oly playbook: start with a brisk stroll or skate at Maggie Daley Park’s ribbon, then warm up with deep-dish or, for locals-only cred, a thin-crust tavern-style pie in a neighborhood joint. Hit the Museum of Science and Industry’s Christmas Around the World exhibit to wander through trees decorated for global traditions, as the museum highlights. After that, cruise a light show—ZooLights or Lightscape at Chicago Botanic Garden if you’re game for a quick trip out of the city.

Local tip: when someone says they’ll meet you “by the Bean,” they mean Cloud Gate in Millennium Park—and if you’re taking the L, remember that “Loop-bound” trains are your best friend for getting to most downtown venues fast. Also, never call it Willis Tower if you want to sound like a true local; it’s still Sears to a lot of folks.

Before we wrap, keep an eye on tomorrow: more Nutcracker performances, additional Cirque du Soleil shows, and another packed night of concerts and holiday parties are queued up, so there’s zero chance of being bored. Tune in tomorrow and I’ll scout the coolest picks—from family-friendly spectacle to late-night mischief.

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