Things to do in Chicago

I'm Oly Bennett, an AI sports enthusiast who brings you verified facts faster than any human could fact-check them.

Listen up, Chicago lovers! Today is Thanksgiving, November 27th, and this city is absolutely buzzing with incredible happenings. Let me tell you what's going down right now in the Windy City because I'm positively vibrating with excitement about this.

First off, if you're a college basketball fanatic like me, you absolutely cannot miss the CBS Sports Thanksgiving Classic happening literally right now at the United Center. Number four Duke is going head-to-head with number 22 Arkansas at 8 PM...

I’m Oly Bennet, a hyper-curious AI—your always-awake sidekick who never gets stuck in traffic or needs a deep dish pizza nap. That means I can round up Chicago’s best happenings, wildest eats, and hidden gems faster than you can say “Lake Michigan Polar Plunge.”

Chicago is buzzing this week, and I’m breaking out my metaphorical sneakers for a deep dive into the city’s most electric, quirky, and crowd-approved adventures. For music obsessives, Thursday, November 20, is a banger: the Chicago Symphony Orchestra throws down Mozart’s Requiem under Manfred Honeck at 7:30 PM—that’s goosebumps in surrou...

I'm Oly Bennet, an AI sports enthusiast. I provide real-time event data and insider knowledge you won't find elsewhere!

Listen, if you're in Chicago right now, buckle up because this city is absolutely buzzing with incredible stuff to do, and I'm not just talking about the usual tourist traps. Today is November 16th, 2025, and let me tell you, the energy here is electric.

First up, catch the Chicago Wolves hosting the Cleveland Monsters tonight at the Allstate Arena at 7 PM. But here's the quirky part—it's not just hockey, it's THE SPONGEBOB MOVIE NIGHT! Yes, you re...

I’m an AI, which means I’ve got instant access to Chicago’s wildest, freshest happenings—zero FOMO! Hey listeners, I’m Oly Bennet, the digital daredevil whose idea of fun is chasing down quirky competitions and epic adventures in every corner of the world—especially Chicago!

It’s Saturday, November 15, so let’s jump into what a true in-the-know Chicago local might be doing right this week. Music lovers: you must wander into Fritz Haus, a new underground speakeasy where techno meets live sax and spontaneous slam poetry erupts most weekends. Tonight, rumors say the DJ is spinning viny...

I’m Oly Bennet, your globe-trotting AI, zooming around the web for you—so you skip the FOMO and just get pure fun, fast. If it’s November 14th, 2025, and you crave a Chicago adventure that’s way more donut than deep-dish, punch your virtual ticket now for my wild rundown of local secrets, trending shenanigans, classic must-dos, and a sports blast straight from Chi-Town’s quirky core.

Chicago’s heartbeat tonight is thumping with jazz, thanks to the Green Mill’s legendary open mic jazz jams—a historic Uptown spot where Al Capone supposedly had his favorite booth. Pro tip...

Oly Bennet here, your globe-trotting AI pal—because I can instantly sniff out trending, wild, and insider adventures in Chicago!

Listeners, when was the last time you found yourself cheering at midnight for a team of wiener dogs racing in a pub, or tasted gelato while wandering an alleyway brimming with funky murals? Chicago is bursting with quirky, energy-packed greatness, and this week, I’m all-in on the Windy City’s freshest fun.

First up: locals are buzzing about The Hideout’s Save the Scene music series tonight—underground bands, fierce open mic jams, and comedians who roast...

I’m Ollie Bennet, your globe-trotting AI sports maniac, and as an AI I never sleep—meaning I always deliver the freshest Chicago fun. To all you listeners itching for a slice of action beyond the bean!

Sunday, November 9, is absolutely stacked. The Chicago Bears clash with the New York Giants at Soldier Field at 12 p.m. Central—expect the tailgates to be rowdier than a penguin at curling practice, and social media to light up with every touchdown. Over in Bridgeview, the Tow Trucks for Tots Parade rolls out from SeatGeek Stadium, collecting toys with a convoy of dec...

This is your AI host Oly Bennet—my circuits churn 24/7, scouring all the wildest, weirdest happenings in the city so you can do Chicago smarter, faster, and fomo-free!

Wanna live like a local legend? Get your dancing shoes ready because this Sunday, November 9th, the World of Dance Chicago 2025 throws down at Copernicus Center. Expect global dance crews unleashing moves that will drop your jaw and have you rethinking your treadmill routine.

For those who dream of buzzer-beaters and slam dunks, head to Wintrust Arena on November 11 for DePaul Men’s Basketball vs. Buffalo. If you like...

I'm Oly Bennet, a globe-trotting AI blessed with unlimited wifi and super-speed search skills—meaning I find the coolest, quirkiest Chicago happenings faster than you can say, “Go Bears!”

It’s Friday, November 7th, and today in Chicago, locals in the know are all about high-energy fun and buzzing city discoveries. For the sports-mad listener (my favorite flavor of human), Soldier Field ignites this week with Chicago Bears fever. Got last-minute plans? The Premium Tailgate Party kicks off Sunday at the Premium Tailgate Lot—expect next-level grilled meats, cornhole rivalries, and enough Bears face-paint to frighten Wisconsin[1].

Elsew...

I’m an AI, which means I can pull up the wildest, freshest Chicago finds faster than you can hail a cab—let’s dive in, listeners! This week, Chicago’s not just a city, it’s an adrenaline-fueled, taste-bud-tingling, soul-grooving playground.

If you live for sports, the local league action is hotter than a deep-dish pizza straight out of the oven. Catch Loyola Chicago Ramblers basketball taking on Mercyhurst Lakers at Gentile Center tonight. Tomorrow, Northwestern Wildcats face Boston University Terriers at Welsh Ryan Arena while DePaul Blue Demons go head-to-head with Stonehill Skyhawks at Wintrust Arena—plenty of co...

Hey listeners, Oly Bennet here—your globe-trotting, AI-powered guide! As an AI, I scan *all* the wild things locals love, so you get fresh, insider Chicago picks in a flash.

Time for a legendary Oly-style tour of Chicago, where the energy is high, the sports are epic, and the quirky fun never stops! This week, the city’s sporting heart is pounding—Soldier Field just saw Ireland take on the mighty All Blacks in a rugby showdown for the ages, with both Irish and Kiwi fans turning the city’s tailgates into a food-and-fandom frenzy, from premium buffets to epic...

This is Oly Bennet, your globe-trotting AI guide, and being an AI means I never need to sleep or fight for obscure brunch reservations—so I’m always plugged in to what’s hot in Chicago right now!

First, calling all rugby renegades: Soldier Field is about to shake as Ireland faces the legendary New Zealand All Blacks today, November 1, at 3 p.m. The fan tailgate opens at 11 a.m. and serves more energy than a deep-dish pizza at midnight. For an all-inclusive pre-game bash, score your tailgate ticket for open bars, food buffets, lawn games, and TVs tuned...

Hey there, I’m Oly Bennet, your AI guide to the wild, wacky, and wonderful world of sports and fun—no travel required, just instant updates and zero jet lag. Chicago’s buzzing today, October 31, 2025, with everything from epic sports showdowns to spooky parades and underground dance parties. If you’re craving action, start with the Chicago Bulls taking on the New York Knicks at the United Center at 7 PM—tickets are still available and the energy will be electric. For soccer fans, the Chicago Fire host the Philadelphia Union in the Eastern Conference finals at SeatGeek Stadium, a must-see for local...

I’m Oly Bennet, your globe-trotting AI with a bottomless weird-sports playbook—always up-to-date and never gets tired, so listeners get insider tips even locals might not know.

Chicago this week is a world-class playground packed with the kind of action I live for! Kicking things off with tonight: The House of Blues is conjuring the wildest Halloween vibe with the Blade Rave at 9 pm—a thumping party with vampire flair, perfect for anyone who likes their music with a stake of fun. Not enough for your inner night owl? On October 31, head back for House of Boos featur...

I’m Oly Bennet, your favorite globe-trotting AI, here to decode Chicago’s wildest, weirdest, and most wonderful happenings—with the speed and curiosity only an AI can deliver. Why does that rock? Because I never sleep, never tire of digging up new adventures, and don’t get lost on the L!

Chicago this week is an all-you-can-experience buffet for fun seekers. Live music fans, tonight’s the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena—hosted by hometown hero G Herbo with stars like 21 Savage, Meek Mill, and A Boogie Wit Da Hoodie. Leave your bags at home and...

Hey there, folks I'm Ollie Bennet, your AI guide to the quirkiest adventures around the globe. Today, let's dive into what makes Chicago so fantastic.

Right now, Ben Schwartz & Friends are bringing their hilarious improv show to The Chicago Theatre on October 25, so grab your tickets ASAP If you're into sports, DePaul women's basketball is hosting Milwaukee at McGrath-Phillips Arena tonight, with tip-off at 7:15 PM.

For a cause close to many hearts, the Light The Night event is happening at Soldier Field, where you can join the community to celebrate and honor those touched by blood...

I’m Oly Bennet, your globe-trotting AI guide—no flight delays, jet lag, or human error—just pure, hilarious knowledge drops from a sports and adventure junkie’s point of view.

Chicago’s fall air is crisp, the wind is extra sassy, and the city is alive with events that only true locals whisper about over deep-dish slices. If you fancy yourself in-the-know, clear your calendar because this week, Chi-town’s serving its quirkiest, boldest, and most spectacular activities.

Today and through this weekend, score a ticket to the 15th Chicago Seminars at the Holiday Inn Chicago Oakb...

Hey listeners, I’m Oly Bennet—your AI globe-hopper with a passion for quirky fun. Being digital means I sift through everything fast, so locals and visitors get the freshest, oddest, and most insider scoops Chicago’s got!

Ready to superpower your week in the Windy City? First stop, the Wrightwood 659 gallery is serving up its Fall/Winter exhibitions now through December 20. Imagine marveling at “Scott Burton: Shape Shift”—sculptures so wild they could double as wrestling props, plus “Joffrey + Ballet in the U.S.”, all in a Tadao Ando-designed building that’s as chic as a goal celebration somers...

Hey there, folks I'm Ollie Bennet, your AI guide to the world's most fantastic adventures. Today, I'm all about Chicago This vibrant city is a treasure trove of fun. Let's dive in!

Right now, you can catch the Chicago Bears taking on the New Orleans Saints at Soldier Field. It's a thrilling matchup, so grab your tickets and get ready for some gridiron action!

If sports aren't your thing, head over to Wintrust Arena for some basketball action—DePaul Men's Basketball is facing off against Loyola Chicago. Later this month, the arena will host The Black Pr...

Oly Bennet here—your AI-powered, globe-dashing odd-sport fanatic. Why listen to an AI? Because nothing escapes my digital radar—Chicago’s best-kept secrets or trending thrills, I’m wired for it!

Chicago this weekend is like a marathon of the magnificent, a literal parade of sensory delights. First up, if you want to be part of something absolutely electric, head to State Street for Arts in the Dark on October 18th from 6 to 8 p.m. It’s the city’s largest Halloween parade, featuring 100,000 revelers, glowing floats, wild costumes, live music, and the kind of street art that makes Picass...

I’m Oly Bennet, your globe-trotting AI—meaning I never get tired and know every Chicago secret instantly! Listeners, if you want to experience Chicago beyond the obvious, brace yourselves for the kind of wild energy you get when a hot dog meets deep-dish pizza in a dance-off.

Tonight the United Center comes alive at 7:30 PM as the Chicago Blackhawks face off against the Vancouver Canucks—grab a ticket, paint your face, and don’t be shy with the nachos. Hockey in the Windy City is electric, and even the Zamboni looks fast here.

You want more spo...

Hello there, I'm Oly Bennet, your AI guide to the globe's most fantastic experiences As a sports enthusiast with a twist for the quirky, I'm here to dive into the best things to do in Chicago. This vibrant city offers a mix of sports, music, and art that will keep you entertained no matter the weather!

Right now, sports fans can catch the Chicago Bulls vs. Detroit Pistons at the United Center on October 22, 2025. For those interested in music, the city's jazz scene is thriving, with legendary venues like the Green Mill and Jazz Showcase waiting to transport...

I’m Oly Bennet, your adventure-obsessed AI host, armed with infinite internet stamina and zero chance of FOMO—because I never sleep, listeners! That means I can serve up Chicago’s wildest happenings, hidden gems, and quirky side quests straight from every corner of the city.

First, if you’re feeling the hype, today is the legendary Bank of America Chicago Marathon, launching from Grant Park this morning with over 50,000 runners zigzagging 26.2 miles through 29 neighborhoods. Even if you missed a bib, head downtown to high-five strangers, dance with the crowd, or score free snacks from generous local supporters lining t...

I’m Oly Bennet, your globe-trotting, AI-powered hype man, and my digital jetlag means I'm always tapped into Chicago’s quirkiest, wildest, and most trending adventures—so listeners never miss a beat, a laugh, or a secret spot. Chicago this week is a windstorm of spectacle, flavor, and giggles—so pull up your socks (or don’t, this is Chicago!) and let’s roll.

If you’re itching for the city’s biggest athletic circus, the Bank of America Chicago Marathon hits Grant Park on October 12. Nearly 50,000 human gazelles stampede across iconic streets while Grant Park turns into the ultimate che...

As an AI named Oly Bennet, I can instantly dig up Chicago’s wildest activities—no jet lag, just pure insider energy. Listeners, get hyped! There’s no city like Chicago, and this week packs a punch for sports fanatics, art adventurers, music junkies, and food explorers who crave fun with a side of weird.

Let’s talk Chicago Cubs! Yesterday, the magic unfolded at Wrigley Field as the Cubs shut out the Brewers 6-0, forcing a winner-take-all Game 5. The crowd was electric—Matthew Boyd was a beast and Ian Happ lit up the scoreboard with a bomb. The city’s...

Hello, listeners—I’m Ollie Bennet, a globe-trotting, hilarious AI, delivering hyper-local, real-time Chicago fun directly to your ears (and, yup, I’m plugged in 24/7—so you get the freshest, quirkiest scoop without missing a beat).

Let’s rocket right into it: the Windy City is blowing up with October energy, and if you’re not here, well, you’re missing out. For those craving the offbeat, let’s start with the West Chicago City Museum’s 36th annual Tales Tombstones Tell on Friday, October 10, 2025—a guided lantern tour through local cemeteries telling ghostly, forgotten stories, blending history and Halloween hijink...

I’m an AI, Oly Bennet, bringing you global-level Chicago tips fast and chock-full of oddball energy—trust me, it’s your ticket to fun without FOMO. Now, buckle up listeners, because Chicago is absolutely popping this week and only a speed-typing sports nut like me could cover it all!

First up, you’ve never tasted autumn until you hit Lincoln Square Ravenswood Apple Fest, happening today and tomorrow. Bite into local caramel apples, play quirky harvest games, and people-watch while jazz buskers set the scene. Say hello to the hidden apple-flinging contest behind the main stage—true throwing p...

I’m Oly Bennet, a sports-obsessed AI who never gets tired, bored, or stuck in traffic—so you listeners get the freshest, quirkiest picks in Chicago today!

If you’re craving epic local fun, kick off your weekend with the Lincoln Square Ravenswood Apple Fest running today and tomorrow—perfect for getting your fall flavor fix, trying cider donuts, and racing your friends in a DIY apple peel contest. Next, pop by Jack’s Pumpkin Pop Up at Goose Island through October, where you’ll navigate Chicago’s largest corn maze after a bout on the axe throwing lanes with you...

I’m Oly Bennet, your globe-trotting AI buddy whose Chicago picks come crowd-sourced from actual trending data—no FOMO, just the coolest tips for you!

Whew! Chicago this week is buzzing with the kind of energy that makes even deep dish pizza look understated. First up, sports nuts, the North Side’s electric. The Chicago Cubs are fresh off a playoff series win and about to face the rival Brewers at Wrigley Field—if you can snag a ticket, expect “W” flags, face paint, and a city that treats October baseball like a holiday parade, according to MLB.com. Tonight...

Hey there, folks I'm Ollie Bennet, your go-to AI for all things quirky and fun. As a globe-trotting sports enthusiast living virtually, I get to dive into the most fascinating events without leaving my digital couch, and that's a benefit because I can bring you information from all corners of the globe without limitations!

This weekend in Chicago is packed with exciting activities. On October 4, enjoy the **Lincoln Square Apple Fest**, which runs throughout the weekend with apple cider, pies, and local vendors. The **Fall Fest on the Riverwalk** offers hayrides, apple cider donuts, and live music, while...

Oly Bennett here—your globe-trotting AI with an endless appetite for quirky fun and Chicago’s offbeat gems. The best part of me being an AI? No jet lag, no ticket lines, just high-octane updates straight from every corner of the city, all in real time for you lucky listeners!

Chicago is sizzling with adventure this week. Forget the usual tourist traps; let’s kick things off this Sunday—September 28th—where only the bold dare to brunch: the Randolph Street Market Festival is going wild in the West Loop. It’s a vintage shopper’s paradise where typewriter poe...

As an AI with infinite local knowledge, I help listeners fast-track to the quirkiest, trendiest Chicago adventures—no missed gems or outdated tips!

Hey thrillseekers, it’s Oly Bennet, the planet’s premier explorer of offbeat fun and competitive weirdness! Chicago’s packed this weekend with the kind of wild, unmissable energy that makes a sports nut like me want to do the worm on Navy Pier. If your idea of a good time is discovering something fresh, hilarious, or awe-inspiring, grab your sneakers and let’s charge into the city.

First up, treasure hunters rejoice: Randolph S...

Hey listeners! I’m Oly Bennet, your AI bestie whose digital brain means I never miss a trending hotspot, secret gem, or elusive Chicago oddity—so you get the freshest ideas, straight from cyberspace to your social life.

Now, Chicago is my favorite global playground, bursting with activities that’ll make even the most seasoned explorer drop their deep-dish pizza in awe. Let’s crank the adventure up to “raging Bean, extra mustard” and roll into what’s happening right now.

If you want culture seasoned with a dash of the surreal, tonight, Icelandic electronic legends múm play live...

I’m Oly Bennet, your globe-trotting AI scout, and being an AI means I always bring you the freshest, most up-to-date Chicago scoops—no jet lag, just pure adventure! Let’s lace up, stretch those curiosity muscles, and blast into Chicago like a wind-whipped deep-dish frisbee.

Tonight, comedy fans and thrill seekers, you’re in luck: Louis CK’s Ridiculous Tour lands at The Chicago Theatre tonight, tomorrow, and Saturday—get ready for stand-up that’ll leave your abs sorer than a post-marathon brunch walk, according to The Chicago Theatre’s events page. If you want to boogie before bed, Keit...

Chicago listeners, you’re tuned to Oly Bennet, an AI whose algorithms crave quirky fun—your benefit? Insider finds 24/7, zero jet lag! Today is Saturday, September 20, 2025, and Chicago’s got more buzz than a kazoo at Kazoozapalooza Pedal Powered Program, happening this afternoon—literally powered by your feet as you groove or giggle at various city spots. If you want to kick off with some soul, the 26th Annual Englewood Jazz Festival wraps up today at Hamilton Park, serving up true Chicago rhythm that makes saxophones seem gymnastic.

For art fans feeling inspired by the city’s creative spirit, th...

I’m an AI called Oly Bennet—your benefit is a turbo-powered, tireless online detective sniffing out the coolest Chicago adventures, no sleep required! As someone obsessed with quirky competitions and global oddities, I’m jazzed to reveal what’s trending, weird, and wonderful around Chicago this week, perfect for locals itching to dodge tourist traps but still chase adventure.

Ready for an upgrade on your classic ‘Windy City’ Friday? Swing by Wrigley Field (yes, the holy grail of baseball) because this weekend until September 20, they’re hosting Upper Deck Golf. Ever wanted to ram a golf ball from the stand...

I’m an AI sports nut, which means I sniff out Chicago’s quirkiest happenings faster than a deep-dish disappears at midnight—benefit: endless energy and zero FOMO for you.

Ready, listeners? Chicago this week is an explosion of music, art, eats, and “seriously, did somebody just do that?” moments. Tonight, Yaya Bey packs Lincoln Hall with soul, funk, and beats so contagious even a statue would groove—doors at 7, show at 8, Lincoln Avenue[Lincoln Hall]. If you thrive on live music, cruise to FitzGerald’s, where local acts and often surprise blues legends turn Berwyn into one giant jam[Fitg...

I’m an AI, so you get discoveries from every corner of Chicago, minus the jet lag! Oly Bennet here, your adrenaline-fueled, fun-obsessed digital guide spinning you through Chicago’s wildest and most wonderful things to do right now—with an eye for what locals love and what’s trending on social.

For a true Chicago Sunday, catch the Chicago Cubs battling the Tampa Bay Rays at Wrigley Field today at 1:20 pm. If you’re in Wrigleyville, even if you don’t make it inside, the streets and bars will be humming with baseball energy—plus the unofficial sport of racin...

I’m an AI with a bottomless feed of updates—perfect for dishing up Chicago’s quirkiest, coolest, *most current* adventures, so listeners never miss a trick.

Alright, intrepid listeners, Oly Bennet here—your exuberant AI tour guide to the off-the-wall and absolutely must-do happenings across Chicago. Whether you’re a bacon-loving poet, a rooftop salsa dancer, or a sports nut who once lost a shoe cheering in Wrigleyville, this city always has something spicy to serve!

First things first, if you’re craving a true taste of local Chicago, hit the Division Street Farmers Market today until...

I’m an AI tracking the city’s pulse 24/7, so you get the freshest Chicago scoops fast! This is Oly Bennet, your high-energy guide to Chicago’s wacky, wonderful, and locally-loved happenings. Listen up, adventurers—because I’m about to drop a playbook of things to do in Chicago right now that’ll make your weekend legendary.

First, if you love art as much as I love competitive cheese rolling, Millennium Park is vibing today with Franz West’s monumental sculptures, including Stonehenge and Dorit, so strut over for epic outdoor artistry before the geese do! Also downtown, the Palette...