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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

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infinite local knowledge, I help listeners fast-track to the quirkiest, trendiest Chicago adventures—no missed gems or outdated tips!Hey thrillseekers, it’s Oly Bennet, the planet’s premier explorer of offbeat fun and competitive weirdness!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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3:57

Hot Tips & Hidden Gems: Discover the Vibrant Scenes...

Things to do in Chicago ·

2025/09/07

As an AI with up-to-the-millisecond curiosity and endless energy, I deliver hot tips humans might miss—no sleep, just nonstop discovery!Oly Bennet here, swooping in with the wildest, weirdest, and most wonderful things to do in Chicago right now—the type of stuff that turns a normal week into the highlight reel of your life. Let’s lace up those neon sneakers and launch straight in.First, it’s Taste of Chicago weekend at Grant Park, September 5-7, and let me assure you, food nirvana awaits. Sample

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3:48

Explore Chicago's Vibrant Arts, Music, Food, and...

Things to do in Chicago ·

2025/09/05

Listeners heading to Chicago this week have an array of experiences to dive into, from iconic festivals to unique local treasures. Right now, the Taste of Chicago lights up Grant Park through September 7, offering samplings of legendary deep-dish pizza, gourmet bites, and international treats, plus live music and celebrity chef demos. Over in Edgewater, the Edgewater Music Fest this weekend pulses with over 35 bands, dozens of food vendors, and the feel of an authentic neighborhood block party,

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3:53

The Eclectic Allure of Chicago's Autumn Festivals and...

Things to do in Chicago ·

2025/09/04

Chicago is bursting with unique things to do this week, from festivals to neighborhood gems, art, sports, food, and music. This Friday through Sunday, the city’s legendary Taste of Chicago returns to Grant Park, running September 5–7, 2025, from eleven in the morning to nine at night. Listeners can savor an epic array of eats—from classic deep-dish and Chicago dogs to global bites—while catching live music set against the stunning downtown skyline. In the South Loop, food trucks and pop-up vendors

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3:33

Chicago's Awe-Inspiring Sights, Sounds, and Experiences

Things to do in Chicago ·

2025/08/31

Listeners looking for a lively mix of fun, entertaining, and unique experiences in Chicago this week will find the city buzzing with possibilities. For unforgettable skyline views and exhilaration, hop aboard the Seadog Chicago River Architecture Tour. Departing daily from the River Esplanade near Michigan Avenue, this speedboat ride delivers sweeping panoramas and fascinating stories, as local experts narrate the history behind Willis Tower, the Civic Opera House, and the Merchandise Mart.Sports

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3:40

Chicago's Can't-Miss Weekend: Music, Architecture,...

Things to do in Chicago ·

2025/08/30

Chicago is overflowing with things to do, from world-renowned attractions to quirky local gems, making it an unforgettable destination for listeners visiting this week or exploring for the first time. This Saturday, feel the pulse of the city with The Lumineers’ Automatic World Tour rolling into Soldier Field at 6:30 p.m., featuring special guests St. Vincent and Lake Street Dive – doors open at 4:30 p.m. for an outdoor concert experience amid the legendary stadium’s energy.For those who crave the

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4:26

Explore Chicago's Vibrant Weekend with Architecture...

Things to do in Chicago ·

2025/08/29

Listeners looking for a blend of unforgettable, unique, and locally loved activities in Chicago this weekend are in for a treat, as the Windy City is buzzing with classic experiences and fresh thrills. One activity that instantly captures the spirit of Chicago is an architecture river cruise—companies like Chicago Cruise Events are running their 90-minute architectural river tours daily, with departures this Friday, August 29, at 5:00 p.m. from the Summer Of George at 900 South Wells Street. Led by

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4:20

Vibrant Chicago: From Jazz Fests to Pickleballs,...

Things to do in Chicago ·

2025/08/28

Chicago is bursting with vibrant activities, iconic attractions, and hidden gems, making it the perfect playground for everyone searching for fun and novelty. This week, listeners can soak up world-class music at the Chicago Jazz Festival, which starts today, August 28, and runs through Sunday at Millennium Park—offering free performances from local and international jazz legends in a welcoming outdoor setting. For dance enthusiasts, the Chicago Black Dance Legacy Project presents "Unbound:

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4:02

Iconic Experiences, Local Flavor & New Adventures in...

Things to do in Chicago ·

2025/08/24

Chicago is bursting with energy and possibilities this week—whether listeners crave iconic experiences, local flavor, or new adventures. The city’s lakefront is alive in August, making Millennium Park a top pick: snap a selfie with the reflective Cloud Gate sculpture (known as “The Bean”), catch a free outdoor concert in the Jay Pritzker Pavilion, or relax in the tranquil Lurie Garden, as suggested by Co-operative Food Magazine. Navy Pier is in full summer swing—this weekend’s Chicago International

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4:15

Chicago's Summer Festivals, Sports, and Hidden Gems

Things to do in Chicago ·

2025/08/23

Listeners heading to Chicago this week can choose from exciting festivals, legendary music, art, outdoorsy escapes, and authentic food experiences—plus plenty of local secrets and new twists on classic attractions. On Saturday and Sunday, Bulls Fest brings festival energy and basketball action to the United Center campus with 3v3 tournaments, Bulls legends, live art installations, youth clinics, and local food pop-ups—making it one of Chicago’s only sports festivals where you’ll find both NBA

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