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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Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday hype man, and today, Thursday, December 18th, Chicago's buzzing with that crisp winter magic—think chilly winds whipping off Lake Michigan around 30 degrees Fahrenheit, perfect for bundling up and diving into festive fun that feels like an epic polar adventure.

Kick off with **Cirque du Soleil's 'Twas the Night Before** at The Chicago Theatre tonight at 7 PM, where acrobats and reindeer flip holiday cheer into jaw-dropping flips—Chicago Theater calls it their 49th original stunner running through December 28th. Families, hit **Senior Fun Day** at Richton Park Community Center or the free Ryan Learning Center at the Art Institute for cocoa and crafts—The Kittchen raves about these indoor gems. Culture seekers, join **Introduction to Irish Singing** at Chicago Gaelic Park in Oak Forest for lilting tunes. Night owls, catch **Holiday Movie Nights** at Winterland at Gallagher Way near Wrigley Field, sipping hot cocoa under the lights—Gallagher Way's got that cozy rink vibe.

Local buzz: Christkindlmarket's still popping with German treats downtown, while CTA's running smooth with no major delays reported today. New spot alert—Elston Electric arcade at Salt Shed pairs kiddo games with grown-up drinks.

Must-dos? Lace up for the Maggie Daley Ice Ribbon's serpentine glide, a Chicago winter classic, or uncover the Balloon Museum's massive ball pit explosion—pure chaotic joy for all ages. Hidden gem: Zoolights at Lincoln Park Zoo, twinkling thousands of lights like a safari light show.

Local tip: Flash a smile and say "pop" for soda—true Chicagoans know it's the bubbly secret handshake that'll have vendors treating you like family.

Tomorrow, Joffrey Ballet's Nutcracker spins into Lyric Opera House—tune in for more wild Chicago quests!

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Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday adventure guide, buzzing with energy on this crisp winter Sunday. Chicago's vibe today is pure festive magic—think twinkling lights, a chill in the air around 30 degrees with possible flurries, and that electric holiday hum as families bundle up for indoor thrills.

Kick off with Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall—rides like the Cliffhanger and Zero Gravity, ice skating on the Verizon Google Pixel rink, a 42-foot holiday tree, and Ferris Wheel spins for all ages, perfect for family fun. Catch Cirque du Soleil's 'Twas the Night Before at The Chicago Theatre with shows at noon, 3 PM, and 6 PM—acrobats, reindeer, and a snowy poem come alive in their 49th original production. Sports fans, roar for the Chicago Bulls versus New Orleans Pelicans at United Center tonight at 6 PM—gates open 4:30, grab those tickets for hoops holiday style. If you're into vintage vibes, hit the Randolph Street Holiday Market at Plumbers Hall wrapping up today from 10 AM to 5 PM—125 boutiques with artisan gifts, fancy foods, cocktails, and free parking for treasure hunting. For culture seekers, Chicago Public Library branches host cozy holiday reads like A Christmas Carol discussions, blending festive stories with community cheer.

Local buzz: No major transit hiccups reported, but bundle up for wind—CTA's running smooth. New spots like Schneider Provisions at markets sling top lox and bagels. Must-dos today? Whirl on WonderFest rides, then Bulls game for adrenaline, or snag Cirque tickets for acrobatic awe—pair with a hidden gem like a Lake Michigan skyline stroll from Navy Pier.

Local tip: Chicagoans swear by the "Polish pretzel" from street vendors near the Theatre—chewy, salty perfection to fuel your day, a Windy City secret since the '80s.

Tomorrow? More Cirque shows and WonderFest ramps up—tune in for the scoop!

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.

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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.

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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.

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Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut buddy, Oly Bennet. Chicago is buzzing today with classic winter-in-the-city energy: chilly temps, big coat weather, and that perfect excuse to power-walk like you’re in your own sports montage along the lakefront.

Let’s kick off with today’s vibe-setters. Over at The Chicago Theatre, Cirque du Soleil brings holiday acrobat chaos in the best way with “’Twas the Night Before…” tonight at 7 p.m., turning State Street into a festive circus playground, according to Madison Square Garden Entertainment. Up in Wrigleyville, Winterland at Gallagher Way is in full swing, with ice skating, holiday lights, and rides inside Wrigley Field itself, as Gallagher Way’s event schedule highlights. It’s like someone turned a ballpark into a snow globe…and then added hot chocolate and beer.

For live music fans, the Hideout’s ultra-intimate stage hosts “Andrew Sa’s Lonesome Holiday” tonight at 7:30 p.m., and the venue reports the show is already sold out, which tells you the holiday crooning game is strong. Art lovers can head to the Driehaus Museum this evening for “Thursday’s Holiday Spirits: A Collection of Victorian Yuletide Ghost Stories” from 6 to 8 p.m., listed on Chicago Gallery News, mixing spooky vibes with Gilded Age glamour. And for a more reflective moment on Michigan Avenue, the Magnificent Mile calendar notes a Peace Concert at Fourth Presbyterian Church, pairing poetry from the Poetry Foundation with new music in a serene chapel right off the shopping chaos.

On the news-and-updates front, Newcity recently highlighted that the Obama Presidential Center has opened a public hoops court, adding a fresh, very-Chicago spin to Jackson Park. That means you can literally go shoot around on a court inspired by the city’s most famous basketball-loving president—streetball meets history lesson. Newcity also reports that Gibsons is coming to Fulton Market, turning that already food-obsessed neighborhood into even more of a culinary power play, so keep that area on your steak-and-cocktails scouting report.

If you’re plotting your day, here are some Oly-approved plays. Hit Navy Pier and the Chicago Children’s Museum for family fun—hands-on exhibits and space for kids to run wild, as the museum’s own visit page describes. Swing north to Gallagher Way for skating and winter festivities, then warm up with a classic deep-dish showdown in Lakeview. Culture fans can double up with an afternoon gallery stop and an evening at the Driehaus ghost-story event, then cap it all off with cocktails in River North.

Local tip for you: Chicagoans treat the CTA like a pro sports strategy. Get a Ventra card, stand to the right on escalators, and when a bus or train door opens—move with purpose. Also, if the wind is howling, use the Pedway downtown, that underground walkway web connecting buildings, to cut your exposure time to “human popsicle” levels.

Before I sprint off to my next weird sporting event: tomorrow brings more holiday concerts, museum happenings, and neighborhood light displays across the city, plus weekend ramp-up energy in Wrigleyville and Fulton Market. Tune in next time as we scout the best picks so your Chicago days stay at championship level.

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.

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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.

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Welcome listeners to Things to Do in Chicago with your globetrotting sports nut pal, Oly Bennett. Chicago this December Saturday is serving classic Midwest winter vibes: cold enough to see your breath, perfect for cozy lights, indoor fun, and a little lakefront braving if you’ve packed your big coat.

The city’s energy today is pure holiday hustle. Navy Pier is in full festive beast mode with Winter WonderFest, running now through early January, turning Festival Hall into an indoor playground of rides, ice skating, a 42‑foot holiday tree, and a ticket that even includes a ride on the Centennial Wheel, according to Navy Pier. If you’ve got kids, or you’re just a big kid who likes spinning in circles and hot cocoa, that’s your daytime slam dunk.

For culture fans, Newcity’s design listings highlight Tracing/Traces: Architecture and the Archive 2025, happening today at 11:30 a.m., a behind‑the‑scenes look at the Art Institute’s architecture archives. That’s your “I’m sophisticated, but I might still hit a dive bar later” move. And for pure holiday magic, Chicago-Theater.com notes that the Joffrey Ballet’s The Nutcracker is on this month, a legit Chicago tradition if you want twirling dancers instead of twinkling LEDs.

Music lovers, we’ve got you. Old Town School of Folk Music is hosting Irish Christmas in America today with family‑friendly shows at 5 p.m. and 8 p.m., mixing Irish music, dance, and stories—think fiddles, pipes, and step dancing instead of your uncle’s off-key carols. Over at the United Center, 107.5 WGCI’s Big Jam roars in with an all‑star hip‑hop and R&B lineup including GloRilla, Sexyy Red, Tink, and more, per the United Center’s event listing. That’s your go-to if your ideal holiday soundtrack is bass, not bells. And if you want a more intimate jam, House of Blues has Sister Hazel on stage tonight, according to their calendar—a perfect sing‑along night out.

On the city news front, this time of year the big theme is transit and timing. Expect heavier crowds on the CTA near the Loop, Navy Pier, and the theater district as folks flock to shows and holiday events, so plan extra time and consider hopping trains over driving and parking chaos. Plus, new seasonal pop‑ups and holiday menus are rolling out all over River North and West Loop, with many spots doing special winter cocktails and late‑night bites—prime pre‑ or post‑show fuel.

If you’re building the ultimate Oly-approved Chicago day: start with a lakefront stroll or Millennium Park wander to check out the holiday décor, then hit Winter WonderFest at Navy Pier. In the afternoon, swing by the Art Institute or that Tracing/Traces architecture event for a brainy break. Evening: pick your lane—Irish Christmas in America for cozy cultural cheer, Big Jam for arena‑level energy, or Sister Hazel at House of Blues for nostalgic rock vibes.

Local tip from your roaming sports weirdo: when you’re downtown, use the pedway—Chicago’s underground walkway system—to dodge the wind and cold between some Loop buildings. And if you order a Chicago‑style hot dog today, do NOT ask for ketchup unless you want your server to judge you harder than a ref at a playoff game.

Tomorrow, keep an eye out for more holiday markets, ongoing Winter WonderFest action, and even more concerts and family events popping around the city. Tune in then and we’ll map out your next Chicago adventure play-by-play.

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.

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