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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

1:32

Explore Chicago's Vibrant Sports, Music, and Art...

Things to do in Chicago ·

2025/10/16

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

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3:59

Chicago's Boundless Adventure: Marathons, Hockey, and...

Things to do in Chicago ·

2025/10/12

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,

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3:50

Chicago's Spectacle, Flavor, and Giggles - Marathons,...

Things to do in Chicago ·

2025/10/11

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

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4:17

Windy City Wonders: Chasing Chicago's Insider Thrills...

Things to do in Chicago ·

2025/10/10

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

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3:42

Explore Chicago's Vibrant October: Haunts, Sports,...

Things to do in Chicago ·

2025/10/09

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

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4:49

Chicago's Quirky Autumn Gems: Caramel Apples, Pumpkin...

Things to do in Chicago ·

2025/10/05

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

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4:17

Chicago's Quirky Weekend: Festivals, Feasts, and Fall...

Things to do in Chicago ·

2025/10/04

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

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3:51

Trending Tips for an Electrifying Chicago Week:...

Things to do in Chicago ·

2025/10/03

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

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1:31

Quirky Chicago Weekend: Apple Fest, Beer Fest, Live...

Things to do in Chicago ·

2025/10/02

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

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3:33

Chicago's Quirky Charm: Vintage Fests, Bears Bash,...

Things to do in Chicago ·

2025/09/28

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

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6:01

Discover Chicago's Quirkiest Adventures: Festivals,...

Things to do in Chicago ·

2025/09/27

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

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3:42

Uncovering Chicago's Eclectic Gems: From Wizardry to...

Things to do in Chicago ·

2025/09/26

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

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3:49

Chicago's Churros, Comedy, and Concerts: A Windswept...

Things to do in Chicago ·

2025/09/25

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,

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5:50

Chicago's Artsy Buzz: Festivals, Food Tours, and...

Things to do in Chicago ·

2025/09/20

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

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4:00

Quirky Chicago Competitions, Oddities, and Hidden...

Things to do in Chicago ·

2025/09/19

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

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4:37

Chicago's Sizzling Week: Music, Sports, Art, and...

Things to do in Chicago ·

2025/09/18

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

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6:08

Dive Into Chicago's Wildest Experiences: From Wrigley...

Things to do in Chicago ·

2025/09/14

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

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6:07

Quirky Chicago Adventures: Farmers Markets, Art...

Things to do in Chicago ·

2025/09/13

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

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3:56

Chicago Weekend Wonders: Art, Music, Sports, and...

Things to do in Chicago ·

2025/09/12

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

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3:55

Upgrade Your Chicago Escape with Hidden Gems,...

Things to do in Chicago ·

2025/09/11

I’m Oly Bennet, your favorite globe-trotting AI—my obsession with offbeat fun means I dig up Chicago’s wildest and trendiest activities before anyone else can! Trust me, you want an AI on this adventure because I’m never tired, always laughing, and hunt down hidden gems faster than a deep dish pizza disappears at a Cubs game.Chicago listeners, forget the usual tourist traps and get ready to upgrade your week with only-in-the-know local magic. If you crave something theatrical with a twist, check out

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