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PODCAST

Things to do in Chicago

Inception Point Ai

"Things to Do in Chicago" is the ultimate podcast for discovering the vibrant and diverse experiences that the Windy City has to offer. Hosted by a team of local experts, this weekly show takes you on a journey through the city"s hidden gems, must-see attractions, and the latest happenings.From the iconic skyline to the vibrant neighborhoods, we"ll guide you through the best of what Chicago has to offer. Whether you"re a lifelong resident or a first-time visitor, we"ve got something for everyone –

society & culture places & travel

All Episodes

4:00

Chicago's Vibrant Weekend Ahead: Music, Comedy,...

Things to do in Chicago ·

2025/11/20

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

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4:33

Discover Chicago's Hidden Sports Gems: Passion,...

Things to do in Chicago ·

2025/11/16

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

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4:34

Catching Chicago's Quirky Competitions and Epic...

Things to do in Chicago ·

2025/11/15

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

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3:47

Chicago Secrets, Sports Blasts, and Offbeat Thrills -...

Things to do in Chicago ·

2025/11/14

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

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3:33

Chicago's Quirky Corners: Wiener Dogs, Murals, and...

Things to do in Chicago ·

2025/11/13

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

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3:39

Chicago Sports, Music, and Culture: Your Weekend Insider

Things to do in Chicago ·

2025/11/09

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

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4:27

Discovering Chicago's Vibrant Weekends: Dance...

Things to do in Chicago ·

2025/11/08

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

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5:13

Dive Into Chicago's Quirky Weekend: Sports, Arts, and...

Things to do in Chicago ·

2025/11/07

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

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3:52

Chicago's Adrenaline-Fueled Playground: Sports, Arts,...

Things to do in Chicago ·

2025/11/06

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

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4:36

A Legendary Oly-Style Tour of Chicago: Sports, Music,...

Things to do in Chicago ·

2025/11/02

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

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4:28

A Sports-Fueled Weekend: Rugby Renegades, Rec Leagues...

Things to do in Chicago ·

2025/11/01

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

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2:44

Halloween in Chicago: Sports, Parades, and...

Things to do in Chicago ·

2025/10/31

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

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4:05

Chicago's Weird Sports Playlist: Blade Raves,...

Things to do in Chicago ·

2025/10/30

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

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3:55

Chicago's Wildest Weekender: Music, Sports, and...

Things to do in Chicago ·

2025/10/26

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

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1:17

Exploring Chicago's Vibrant Arts, Sports, and...

Things to do in Chicago ·

2025/10/25

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

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4:24

Chicago's Quirky, Bold, and Spectacular Fall...

Things to do in Chicago ·

2025/10/24

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,

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3:27

Offbeat Adventures, Quirky Finds, and Insider Scoops...

Things to do in Chicago ·

2025/10/23

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

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1:35

Explore Chicago's Thrilling Sports, Arts, and Outdoor...

Things to do in Chicago ·

2025/10/19

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

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3:48

Thrilling Weekend in Chicago: Art Parades, Sports...

Things to do in Chicago ·

2025/10/18

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,

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3:51

Chicago's Thrilling Secrets: Blackhawks, Funky Eats,...

Things to do in Chicago ·

2025/10/17

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

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