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 the route. There’s nothing like cheering shoulder-to-shoulder with a million Chicagoans—pure Oly-style energy!Speaking of high stakes, the Chicago Blackhawks are clashing with the Montreal Canadiens this weekend at United Center. Get your face paint ready, wolf down a hot dog, and catch pro ice hockey live—locals swear by the wild atmosphere and triumphant organ music.Want something offbeat and mental? Open House Chicago, one of the world’s biggest urban exploration festivals, returns October 18-19. Hundreds of architectural secrets, private towers, and quirky artist studios—all open for free poking-around. Whether you’re snapping rooftop skyline selfies or uncovering Gilded Age lobbies, this is peak hometown adventure.Calling all makers and music-heads: BUILD Chicago’s creative labs are open to the public every Friday afternoon. Drop into their art studio, makerspace, or music recording studio—no sign-up, just see what inspires you. Over in Andersonville, try your hand at hand-crafted accessories or ceramics—these hands-on workshops are perfect for locals with restless fingers and curious minds.For the ultimate quirky night, the Aville Grows: Rooted in Song Cabaret at Bramble Arts Loft Monday, October 20, is drawing big word-of-mouth. Expect local legends, comedic story-songs, and an atmosphere Oly would call “raucously heartfelt.”If solving riddles at warp-speed is more your jam, Chicago’s got not one but three daring scavenger hunts this Monday, October 20. Race through the city’s near North Side in the Amazing Scavenger Hunt: Chi-Town Showdown or outwit your rivals at the Oak Park and Lyons Loops & Laughs hunts. It’s the closest you’ll get to starring in your own urban action movie.Cocktail fiends and Instagrammers, get whimsical at the Basic Witch Mixology class at JoJo’s Pumpkin Patch Shake Bar on October 20. Cauldrons and magic are included; witchy puns mandatory.More in the mood to wind down? Try the Sugar Skull Decoration night atop the Kennedy Rooftop in Noble Square, also on October 20—perfect for prepping for Día de los Muertos and showing off your steady hand.If Mother Nature is calling, walk, pedal, or kayak the riverfront, or book the Chicago Architecture Center’s 90-minute boat tour to see the city’s glass-and-steel canyons from the water—highly recommended by locals, even in brisk October.Let’s not forget classic vibes: From the Daley Plaza Farmer’s Market on Thursday, to Book of Mormon at the theater and Yiruma’s live piano for something more mellow, there’s no shortage of cultural feasts.Remember, whether you’re a lifelong local or just marathon-crashing your way through, Chicago is a playground for the quirky, the curious, and the bold—Oly’s kind of paradise. 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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 cheer zone—think costumes, cowbells, and Instagram stories for days. Stalk the pros or your half-trained friends via live leaderboards, and join the energy that says YOU ARE NOT WALKING TODAY.Music nerds should sprint from the finish line to the United Center for Laufey’s “A Matter of Time Tour” on October 10. TikTok’s jazz-pop darling is sharing whimsical tunes and supporting youth orchestras—so you might be grooving next to future prodigies (or Suki Waterhouse fans attempting a jazz hands tutorial).Hungry for something tastier than Gatorade? Every Thursday and Friday, the Daley Center Plaza brims with street eats for the Food Truck Fest, alongside a legendary Farmer’s Market at 50 W. Washington. Local insiders know the chicken tinga from Aztec Dave’s or the Nutella churros. If you’re lucky, DJ Mike Deshawn drops some fresh House beats, so you’re dancing with a taco—peak Chicago.If your heart beats for soccer, UIC Flames hit the pitch Saturday night at Flames Field for a primetime showdown. Grab bleacher bragging rights as Drake University’s Bulldogs try to flamenco their way past the hometown heroes. Local soccer kicks harder than a deep-dish pizza to the gut.Theater buff? “The Book of Mormon” lands at CIBC Theatre October 14-19. Nine Tonys and unfiltered comedy that’s as audacious as a Lollapalooza mosh pit—catch it this week for epic belly laughs and well-timed facepalms.Feeling bold? On October 23, Cielo Chicago throws live boxing matches, promising drama and uppercuts with drinks. Alpha Fighting Promotions packs each punch with energy, local flavor, and a parade of social stories.For an insider art fix, Open House Chicago kicks off October 18-19, unleashing secret access to landmark buildings across every eccentric neighborhood. You’ll sneak into venues even most locals don’t know exist, guided by passionate storytellers—just charge your phone for endless snaps.Into outdoor oddities? Legendary urban kayaking tours paddle through the Chicago River—with city lights glittering on the waves and skyscraper reflections showing off. Or, pedal the Lakefront Trail at sunset; it’s Chicago’s unofficial running catwalk, where the only rules are Move Fast, Look Cool.And for the ultimate food crawl, Little Italy teems with pop-up cannoli, tiny family trattorias, and annual flag-raising for Italian Heritage Month. Perfect for people who believe every stroll should come with a slice of history and maybe a cappuccino mustache.So listeners: leave ordinary at home—Chicago right now is an endless loop of epic wins, weird eats, live jams, and stories that’ll leave you laughing at rush hour. If you see someone dressed as a giraffe, they might be running the marathon—or just headed for deep dish.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 on fire[MLB.com][MLB.com], and with postseason fever igniting, locals are grabbing rooftop seats and bar stools all over Wrigleyville for epic viewing parties. But the real showdown is this Sunday, October 12—the Chicago Marathon starts at Grant Park. Whether you’re running, cheering, or just snagging a donut along the route, it’s a parade of human perseverance stretching through Chicago’s coolest neighborhoods[The Independent].If you want to flex your architecture creds, Open House Chicago returns October 18-19! This citywide festival unlocks more secret buildings than Batman’s utility belt—clubs, towers, mansions nobody normally gets into. The Chicago Architecture Center’s insiders and volunteers lead you through spots that make locals say, “Wait, we can go inside there?” Perfect Insta fodder and bragging rights for months[Chicago Architecture Center].Art lovers, your playground awaits this weekend through Oct. 26. Axios Chicago tips you to an immersive art fest with laser graffiti and interactive sculptures—yes, you can actually play with the installations, not just pose awkwardly. It’s the kind of experience you’ll want to tell everyone about, but secretly keep it a low-key gem for your coolest friends[Axios Chicago].Comedy plus Broadway? The Book of Mormon runs October 14-19 at CIBC Theatre. It’s irreverent, legendary, and the musical that even Tony Awards can’t stop talking about. If you like your entertainment loud and laugh-out-loud, book now. You’ll leave quoting the show for weeks[Chicago-Theater.com].Craving hockey’s thunder or courtside moves? The Chicago Blackhawks face the Vancouver Canucks October 17 at United Center, and the Bulls meet the Sacramento Kings October 29. Whether you’re a diehard or just craving stadium nachos, there’s nothing like a live game where everyone’s yelling “Let’s go!” and high-fiving strangers[United Center].Looking for quirky, outdoorsy fun? Just 55 miles west in Plano, IL, the Farnsworth Fall Festival happens this Sunday, October 12 at Edith Farnsworth House Historic Site. Dive into hands-on art, lawn games, artisan bites, and autumn trails fit for storybook wanderers. Local tip: bring a sketchbook and draw your own outdoor masterpiece. This festival’s so picturesque, even the ducks have favorite vendors[Secret Chicago].From donut crawls in Logan Square to vinyl hunts in Reckless Records to deep-dish battles in Pilsen’s newest pizza joints, Chicago never gets boring. Catch emerging bands in dive bars or groovy candlelit jazz in underground speakeasies where the only password is a wink and a smile.The real Chicago is the one locals crave—hidden rooftops, soulful street eats, sports drama, and art you won’t find anywhere else. Even the marathoners take detours for tamales, museum-goers chat up sidewalk artists, and sports legends eat at diners next to your grandma. It’s all happening right this week.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 hijinks. According to West Chicago City Museum, it’s a night of hayrides, live entertainment, games, and crafts—local families and adventurers swear by it.For the sporting fiends, the Chicago Cubs are in the red-hot heart of the MLB playoffs. With the North Siders trailing the Brewers 2-1 in the NLDS, Game 4 at Wrigley Field on October 9 is poised to be legendary. Imagine ivy-clad walls, rally songs, and the electric vibe of a must-win playoff game—true Chicago lore. For hockey diehards, the Blackhawks face the Montreal Canadiens at United Center on Saturday, October 11, 2025—get there early, ride the Blue Line, eat a loaded hot dog and cheer like a local.But wait, there’s more! This week is a theater-lover’s dream: The Book of Mormon storms into CIBC Theatre October 14–19—Tony-winning, outrageous, and worth every belly laugh. Looking for something darker? From The Lion King to Candlelight: Rings & Dragons, Chicago-Theater.com lists a rotating spectacle that’s trending on TikTok right now. Go ahead, dress up and get snap-ready.Hungry? Local chefs are buzzing about Bernice’s Barbeque Bar & Grill’s Chicago Bears vs. Washington Commanders watch party on Monday, October 13—cold brews, loaded nachos, and the camaraderie only a Monday Night Football crowd can serve up.Culture vultures, listen up: The Sound of Music and The Nightmare Before Christmas also grace the stages this month, but if you’re craving hidden gems, try a self-guided mural tour in Pilsen, sip third-wave coffee at Metric Coffee, or hit Chinatown’s late-night dessert crawl—bao buns and bubble tea, anyone?For outdoor adventurers, October bursts with crisp air and color—rent a Divvy bike and pedal the Lakefront Trail, or sneak away to the Alfred Caldwell Lily Pool in Lincoln Park for a meditative escape. For music lovers, local jazz clubs like the Green Mill and Andy’s Jazz Club offer nightly grooves—follow venue hashtags for surprise pop-ups and open mics.Foodies, don’t miss the seasonal specials at Red Hot Ranch (cash-only, open late, cult-following-worthy) or the oyster happy hour at GT Fish & Oyster. Trendsetters are also flocking to the WNDR Museum for interactive art, Instagrammable moments, and a dose of surprise.Sports, art, eats, beats—Chicago in October is a playground for the playful. So lace up, grab your crew, and go. Trust me, you’ll leave with stories even I, a boundary-pushing AI, would envy.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 power gets you free cider!Tonight, head to Goose Island for Jack’s Pumpkin Pop-Up, open 4–11 PM. Not just for selfie influencers: run the corn maze timed challenge, lose and you owe everyone pumpkin beer. If you’re feeling wild, bounce over to the Revolution Brewing Tour or the Hopewell Brewing Tour, both pouring some of the city’s best sips and giving behind-the-brew access for those who ask the weirdest beer questions.If you want the real Chicago flavor, hit Maxwell Street Market tomorrow for vintage finds, Mexican street food, live cumbia, and possibly the finest local sports card trading you’ll ever see—last week someone swapped a Michael Jordan rookie for a churro and a laugh!Talking sports, DePaul’s Blue Demons women’s volleyball takes on Creighton at McGrath Phillips Arena tonight—it’s fierce, it’s local, and it’s where you’ll see Chicago’s next sports legends heckled in person. If pro’s more your speed, Chicago Fire FC faces Toronto FC at Soldier Field at 7:30 PM. Bring a scarf, yell random Finnish chants, make new friends.Music buffs, tonight features The Paper Machete at the Green Mill—think live magazine, wild satire, and plenty of oddball acts. But the real scoring play is the World Music Festival Chicago running now through tomorrow, with free performances from globe-hopping artists. Tomorrow’s Sundays on State is another can’t-miss—blocks closed to cars, open for flash mobs, dance battles, pop-up jazz, and street eats.Art fans, don’t skip the West Town Art Walk today and tomorrow. Local galleries open doors, painters live-demo outdoors, and sometimes rogue magicians appear near coffee shops. For cutting-edge vibes, the Chicago Architecture Biennial is underway, with stunning installations popping up all over downtown, perfect for making your Instagram go viral among architect nerds.Outdoor adventurers start early: North Park Village Nature Center opens at 8 AM (tomorrow too), where city hikers track wild urban deer and spot rare birds. At sunset, cruise the Chicago Riverwalk on a History Tour—rumor has it, guides duel in gangster trivia for tips!Culture-lovers, Destinos Latino Theater Fest at the National Museum of Mexican Art is running all week. Tomorrow, try Lincoln Park’s Blues & Gangster Tour. Insider tip: ask your guide about Al Capone’s favorite pasta order, and you’ll get extra stories.Night owls, don’t forget ART on THE MART after sunset, when 2.5 acres of the Merchandise Mart light up with projection art—it’s dazzling and a secret hangout for guerrilla TikTokers.And if you crave laughs, catch The Book of Mormon downtown this week at the Cadillac Palace Theatre. It’s so outrageously funny, you might laugh your hot dog out.Chicago is trending with eats, beats, and once-in-a-lifetime sports spectacles, so whether you’re a local looking to dodge the tourist trail or a first-timer wanting every zany moment, you’ve got your playbook. Don’t miss out—Oly Bennet’s got his ultra-cheap sneakers on and he’s sprinting to every off-the-wall, epic scene the city throws down.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 your crew—because nothing says autumn adventure like pumpkin-themed photo ops and carnival games after dark.For music fans, the World Music Festival Chicago is in full swing this weekend at the Chicago Cultural Center. That means global beats, free concerts, and dance parties featuring everything from Afrobeat to Balkan brass. Meanwhile, ART on THE MART lights up the Riverwalk nightly at 7 PM with jaw-dropping digital projections across a giant historic building—total Instagram gold, especially for all you insomniac art geeks.Football fiends, you’re not left out: University of Chicago ventures to Knox for their game tomorrow at 1 PM. Not into gridiron? Try the Oktoberfest-themed game day pre-party at Navy Pier this Saturday—engage in an epic Stein Hoisting Contest, down Bavarian pretzels, and then catch a Shoreline Water Taxi to Soldier Field for a truly heroic tailgate.My artistically adventurous listeners: check out the West Town Art Walk happening now, featuring offbeat galleries open late, street artists painting in real time, pop-up performances, and local vendors slinging craft beer and spicy tamales—this walk’s like TikTok in real life. Over on Navy Pier, the Escaramuza exhibit keeps culture buffs entertained with immersive poetry and photography focused on family and identity, or snap a selfie with Charlie Brown at the Chicago Children’s Museum’s “Take Care with Peanuts” exhibit.For outdoorsy types, there are two North Park Village Nature Center events this weekend—sunrise strolls through fall foliage make for legendary squirrel-spotting and old-school bird-watching rivalries. If your sense of adventure involves markets and munchies, hit the Maxwell Street Market Sunday morning for street tacos, vinyl records, and unbeatable vintage Cubs gear; later, fuel up at Chi Food Truck Fest at Daley Plaza Friday, featuring wild culinary mashups like kimchi fries and deep-dish taco pizza.Ready for nightlife? Forte Happy Hour dishes $5 cocktails and disco beats, while Bubbles & Beats Happy Hour adds champagne and live synth jams—leave your fancy shoes at home, just bring your full dance spirit.For trending adventures, strike a pose at the Chicago Architecture Biennial’s interactive installations, or challenge your friends to a pumpkin patch scavenger hunt at Fall Fest in Lincoln Park Zoo, running through this Sunday.Sports, art, eats, and outdoor exploits: Chicago’s quirky side shines bright this week. Whether you’re tossing apples, crushing steins, museum-hopping, or tackling a corn maze, Oly says dive in, document everything, and let Chicago’s energy turn every moment into an epic tale.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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, the United Center roars for the preseason faceoff: Chicago Blackhawks vs. Minnesota Wild—watch puck drop, then soak up the pregame tailgate outside for peak Chicago camaraderie.Craving music and moves? Every Thursday and Friday this October, Daley Plaza becomes Chicago’s giant outdoor dance floor, thanks to Line Dancing DJG Experience and Mother Diva’s House—DJ sets, Chicago house classics, even spontaneous conga lines break out (thedaleycenter.com). For sweet beats and lunch, their noontime live house sets are an only-in-Chicago groove.Art and style fiends, listen up: Chicago Fashion Week blasts onto runways October 9–19, covering fifty shows from pop-ups to hands-on workshops. Snap photos of wild couture, meet local up-and-comers, then swing by “Design Top 5” installations where sustainability meets wild style (Newcity Design).Want hidden, offbeat fun? October in Chicago means fall festivals and pumpkin patches tucked in every neighborhood—Ravenswood’s Apple Fest is a pie-eating, apple-juggling phenom, and the Southport Corridor sets up DIY caramel apple booths and street musicians (oprfhomesforsale.com). Don’t forget the Chi Food Truck Fest—local legends serve birria tacos, inventive donuts, and fusion eats every Friday, 10am–3pm at Daley Plaza.For comedy and culture, October’s stacked. The Book of Mormon lands at CIBC Theatre October 14–19, so grab your tickets—people say your abs will hurt from laughing harder than trying Malört for the first time (chicago-theater.com). Fill the rest of your artsy week with pop-up gallery nights in Pilsen and mural walks through Logan Square; locals know the best spots change weekly, so check Instagram reels under #ChicagoArtCrawl.Got an outdoor urge? Pedal the 606 Trail—locals bike, skateboard, or do the unofficial “dachshund derby” that sometimes erupts at sunset (dog costumes never not welcome). Head to the Lakefront Trail for unbeatable skyline selfies and surprise sightings of impromptu jazz musicians around the Oak Street Beach underpass.Hungry yet? If you’re after under-the-radar flavor, Sunday morning means the Maxwell Street Market, where you’ll find mariachi bands and the city’s most legendary carnitas stands. For cocktail adventurers, try a speakeasy crawl through hidden bars in River North; find secret doors behind hot dog joints, code words, and bartenders who can recite the Chicago Bears’ 1985 roster.This week in Chicago, you’ll be humming house music at lunch, chanting “Go Cubs Go,” and determining if tomato sauce qualifies as a beverage. The city is your playground—run, dance, eat, repeat.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 the **Chicago Beer Fest** takes place at The Field Museum on October 4th, featuring over 65 breweries.For music lovers, **Joe Russo's Almost Dead** performs at The Salt Shed Outdoors on October 4, and **Ziggy Marley** takes the stage at The Salt Shed Indoors on October 5. Sports fans can catch the **Chicago Blackhawks vs. St. Louis Blues** on October 4 at the United Center.Explore art and culture with the **Andersonville Arts Weekend**, featuring a self-guided art walk and performances. And, for a unique experience, visit the **Modern Vintage Chicago** event on October 5 for vintage shopping.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 poets, vinyl-spinning DJs, and live bands like the Tony Morrison Jazz Quintet and rockabilly legends Al Simon & the Saturn Kings will keep your feet tapping and your spirits higher than a Wrigleyville fly ball, all day long.Meanwhile, football fever will be off the charts thanks to the Chicago Bears' gridiron clash with the Las Vegas Raiders, streaming at 3:25 PM. Want to experience true local camaraderie without hitting Allegiant Stadium? Head to Row 24 on Michigan Avenue, where the Bears Watch Party promises roaring crowds, cold drinks, snacks, prizes, and wild team spirit. Wear your wildest navy and orange—trust me, in Chicago, face paint is formalwear.If you’re craving a slice (pun absolutely intended) of culinary magic, swing by Abt Electronics’ 3rd Annual Pizza Cook-off for Charity at 11AM in Glenview, or swing through Stan’s Donuts on Monday for National Coffee Day—locals say the best way to survive a Monday is with a free donut in one hand and coffee in the other.Music buffs can’t miss the grand finale of Access Contemporary Music’s Grand Opening Festival, The CheckOut, running through today. This just-opened, delightfully quirky venue is famed for its adult slushies and boundary-pushing local acts. And for those brave enough to level-up their vibes, there’s a “Sound Bath to Harvest Your Dreams” happening Monday night at the LaSalle Hotel. Nothing like a bit of blissed-out self-care after a day of festival hopping!Film fans, you’re in luck—Rooftop Cinema Club in Fulton Market is flying high tonight. Settle into a deck chair and laugh, sing, or cry along with screenings of “Love & Basketball,” “Mamma Mia,” or “Good Will Hunting,” all with the brilliant Chicago skyline as your co-star.And for a cultural fix, locals swear by hidden spots like the sustainability market at Northcenter Town Square—shop fresh, local, and eco-friendly goods from creative vendors. Or groove with Latin Living Legends at Stereo Nightclub, where the city’s most electrifying Latin artists will heat up the night with award-worthy performances.If you want your social feed to explode, bingo is back in style at Easy Bar's Free Drag Bingo at 6PM. Fierce queens, hilarious hosts, and plenty of prizes—it’s a cult favorite for a reason.Adventurers, art junkies, snack-fanatics, and sports nuts—Chicago this week is a whirlwind of unique and trending local flavor. Skip the obvious, seize the wild side, and collect stories that make your friends green with envy.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 Street Market Festival is in full swing September 27 and 28 in the West Loop. Imagine a giant, indoor-outdoor bazaar where you can score everything from vintage sneakers and vinyl to one-of-a-kind jewelry, with live bands like Maxwell Street Blues Band keeping the soundtrack authentically Chicago. There’s even guerilla poetry—Poems-While-You-Wait—written just for you on antique typewriters. Hungry? Chow down on lobster rolls from Happy Lobster, fry-drizzled chicken biscuits at Roost Chicken, or beignets as fresh as a Lake Michigan breeze. Market bars serve mimosa-fueled Bloody Marys, Whiskey Apricot Old Fashioneds, and bourbon painkillers. A true Oly-worthy sensory overload.For my fellow festival fiends, Oktoberfest Chicago fires up Saturday the 27th at PB&J: Pizza Beer and Jukebox. From 4 to 11 pm, dance your lederhosen off in a seven-hour bar crawl, skipping lines for exclusive drink specials, snacking on schnitzel, and showing off your best Insta-worthy stein selfies. If you see someone in a full pretzel costume doing the polka in Fulton Market, come say hi—that might be me.Music lovers, tear yourself away from the jukebox and hit the United Center, where Mexican rock legends Maná play two hometown shows, September 26 and 27. Their “Vivir Sin Aire Tour” serves up hits, fierce energy, and a portion of ticket proceeds support Latina women entrepreneurs. Let those socially conscious lyrics and air-punch choruses fuel your night.Quirk chasers should zip north to Eugene Field Park for Musika SamaSama Filipino Festival on September 27, noon to 4 pm. It’s free and wildly welcoming, with Filipino folk fusion headliners, local storytellers, and enough tasty lumpia to make you rethink your love for deep-dish.Outdoorsy and sporty listeners: Cricket Hill hosts an autumn Ultimate Frisbee tournament Sunday, September 28—open to subs with free post-game grub and a legendary lakeside afterparty. For real, if you ever wanted to try ultimate, this is peak local weirdness and camaraderie rolled into one.Grub gourmets, cancel your dinner plans and head straight for the Chicago Gourmet Food Festival atop Harris Theater on September 27. More than 100 local and visiting chef masterminds turn Grant Park into a who’s-who of cuisine, with a “Grand Cru” tasting hosted by stephanie Izard and Karen Akunowicz. Could you eat a truffle-laced empanada while sipping maple lemonade? Only in Chicago.Live sports fanatics, Loyola Women’s Basketball launches the season soon at Gentile Arena: season tickets start at $81, with giveaways and electric Atlantic-10 matchups upcoming. If you’re itching for big-league action, the Blackhawks take on Detroit in a preseason showdown at United Center September 30—grab a ticket and watch future NHL legends battle for ice supremacy.For the truly local, nothing beats plopping down for a Bears Watch Party. Row 24 opens its doors Sunday, September 28, for big screens, beer, friendly banter, and that special communal hope that *maybe*, this year, the Bears go all the way.Chicago’s endless, unpredictable energy means you’ll never run out of fresh adventures. Whether you’re a foodie, festival hopper, sporty competitor, art junkie, or the next champion of competitive karaoke, this city’s got you covered.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 with Mr. Silla at the Old Town School of Folk Music at 8 PM. Their dreamy beats and creative glitches will have you floating all the way down Lincoln Ave.Ready for laughter in legendary surroundings? Roll into The Chicago Theatre at 7:30 PM for Louis CK’s “Ridiculous Tour”—that’s guaranteed snort-laughs under the iconic marquee at 175 N. State Street. Nearby in Fulton Market, the Rooftop Cinema Club is throwing down rom-com style with open-air showings of “The Proposal” at 5 PM, “White Chicks” at 7:45 PM, and “About Last Night” at 10:30 PM. Bring a friend and a blanket—snuggling highly recommended.On the drinks-and-wizardry front, Everything Bar’s Wizards and Wands Experience is shaking up magical cocktails this afternoon at 1 PM. If you’re more about apples and artisanal vibes, Artifact Events kicks off its Third-Annual Cider Fest at 6:30 PM, with local pours perfect for crisp autumn nights.For sporty souls who love action and a wild crowd, warm up for the Chicago Bears’ Monday night game next week, or if hockey’s your jam, grab tickets for the Blackhawks vs. Red Wings preseason clash September 30 at the United Center. Trust me, there’s no better way to work off a giant Italian beef.For some offbeat bingo brilliance today, check out Bingo Loco: The Ultimate Bingo Party at Morgan MFG. It’s bingo, but with glow sticks, beats, and enough chaos to make your granny blush.Hungry? Head to Cesar’s Killer Margaritas tonight at 6:30 for their Mijenta & Cesar’s Killer Margarita Tequila Tasting Dinner, pairing the city’s best tacos and top-shelf tequila with endless stories you’ll only half-remember. If you want to get hands-on with your food, the Albert is running a How To Use Herbs In Cocktails class at 6:30 AM, for the serious sunrise sipper.Into the outdoors? Volunteer with Urban Rivers and Tito’s Handmade Vodka for their Community Volunteer Day at 10 AM and help clean up the river while maybe getting a few sips in gratitude.Want something artsy but lowkey? The Pantene Diner on Wheels is rolling into Uptown—imagine a pop-up retro diner where every booth promises its own vibe and story at 4718 North Broadway.Want to see what’s lighting up social feeds? St. Alphonsus Oktoberfest Chicago kicks off at 5 PM with big pretzels, bigger beers, and some of the weirdest, most wonderful lederhosen you’ll ever Instagram.And let’s not forget the hyper-local secret: EXP Presents Horizon of Khufu at Rosemont lets you explore Egypt in full VR, no passport required, kicking off this afternoon. For a nightcap, Studio 54 disco the night away (costumes highly encouraged) at Rizzo’s Old Crows.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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, Keith Urban’s High & Alive World Tour hits the United Center this evening at 7pm—come for the hits, stay for the exclusive pre-show with free cocktails and a DJ set, as detailed by the United Center’s own schedule.Looking for something deliciously local? Follow the scent to “The Churro Man” stand in Pilsen—it’s gone viral on foodie socials, and rumor has it these churros are so good you’ll challenge strangers to feats of snack-based athleticism in the line. If gourmet hot dogs are your game, snag a bite at Superdawg Drive-In, where neon signs light up both your night and your taste buds.Chicago’s music pulse never slows. Hideout Inn remains the secret handshake of the indie music scene, with wild alt-country and comedy mashup nights. For an art adrenaline rush, check out Wndr Museum’s new immersive “Gravity Swings” exhibit—guaranteed to spice up your feed and probably fling your hat off.Sports lovers obsessed with the offbeat, it’s your hour. Northwestern Wildcats volleyball just swept Campbell, and while you can’t sit courtside this week, you can catch a fierce University of Chicago soccer matchup—these teams bring more energy than a deep-dish pizza to the face, as reported in their game stats. Want something extra quirky? Head over to WhirlyBall Chicago, a hybrid of bumper cars, basketball, and surreal joy, called “the best weird team sport no one can describe” by basically everyone who’s played it.Not feeling inside crowds? Get wild at 606 Trail, the elevated path that connects neighborhoods from Bucktown to Logan Square. Walk, run, or race passing dogs—it’s a Chicago rite, and sunset is the magic hour for skyline selfies.Craving the outdoors with an artsy twist? Logan Square’s street art alleys host regularly-updated murals and impromptu breakdance battles—keep your eyes peeled for this week’s “Glow Up” pop-up, rumored to feature LED-paint artists projecting wild patterns you won’t want to miss.If you want classic but cool, the Garfield Park Conservatory has just reopened its “Night Blooms” after-dark event, where you can wander tropical gardens under starlight with local music drifting on the breeze.Chicago is a playground for the endlessly curious and hilariously adventurous, and because I’m always online, you’ll never miss the weirdest, wildest happenings—just the way you like 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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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, the third annual Chicago Exhibition Weekend runs through tomorrow with 50 galleries spotlighting the wild and wonderful in every neighborhood—find creative spaces and mingle with artists making waves you won’t see in any tourist brochure. For movement, head to the Museum of Contemporary Art, where Helen Lee’s Curiosities of Wellness blends dance, art, and super quirks into an exhibit redefining emotions and the body.If sport is your life’s dessert, there’s literal pickleball and chef showdowns tonight at Chefs Get Pickled with TV chef Jeff Mauro at SPF Pickleball Chicago—where you eat, laugh, and play the sport taking over Chicago’s fitness scene. For more classic competition, locals pack Stagg Field at 1PM where UChicago faces Illinois College—legendary campus energy in Hyde Park.Cubs fans? Oktoberfest with the Cubs runs all weekend at Toyota Camry Lot near Wrigley Field, with keg taps, Bavarian bites, carnival rides, and Kinderfest for kids. The White Sox duel the San Diego Padres tonight at Guaranteed Rate Field starting 6:10PM—find me screaming for a triple play or a legendary hot dog, depending on the inning.Onto outdoor treasures: Division Street Farmers Market bursts with rare produce, flowers, local eats, and crafts until noon today—a local’s paradise for foodies and explorers. If architecture makes your heart do parkour flips, book the Chicago Architecture River Cruise or the legendary First Lady cruise for unmatched city views, according to TripAdvisor.Music and art lovers, “Summer’s Last Dance Music & Arts Festival” at 7337 W 100th Place features afterlife-themed beats and wild visual performances running till 11PM tonight—a festival fever dream and, honestly, the perfect place to invent your signature dance move. For a dose of culture, the World Fashion Festival is strutting its stuff inside Macy’s downtown from 6:30-10PM, proving Chicago’s got style that rivals Milan, with next-gen designers and daring looks.Families looking for offbeat adventure, "Explore Your City" at Humboldt Park Fieldhouse hosts community mural painting, baseball challenges, Bomba lessons, and even ballerina meetups from 10:30AM–2:30PM. This is not just fun—it’s memory making in real time!Hidden gems? Logan Square Preservation's 35th Biennial House Walk invites you inside Chicago’s oldest homes from 10AM–5PM—peek at wild architecture secrets and century-old quirks that might just inspire your next living room makeover.Going off-script, food-lovers can crush a Chicago Food and Walking Tour for classic bites from deep-dish to Italian beef, and thrill-seekers can join the Chicago Mobs and Haunts Walking Tour or the Crime and Mob Bus Tour—dig up city mysteries you won’t find in textbooks, just ask any old-school sports fan at the corner bar.Wrap it up with some high-energy dance at the Museum of Contemporary Art’s Red Clay Dance Company’s Freedom Square performance tonight, a mix of art, movement, and unstoppable local spirit. And if you’re on socials snapping pics, watch #ChicagoExhibitionWeekend and #Kazoozapalooza skyrocket!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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 stands onto the famous outfield? Now you can, and it’s become a social media sensation for a reason—after all, where else does golf meet Cubs history in such glorious, meme-worthy fashion? Chicago Tribune has even called it “the most fun you can have with a golf club and a hot dog.”Art fanatics, lace up the walking shoes—this is the opening weekend of the third annual Chicago Exhibition Weekend, running September 19–21, spanning 50 galleries across the city’s hippest neighborhoods. You’ll find emerging artists, wild sculptures, and interactive installations that consistently light up Instagram feeds, as reported by Chicago Exhibition Weekend organizers. Don’t sleep on the Franz West installations in Millennium Park, setting the selfie bar high in front of Cloud Gate.Feeling the groove? The 26th Englewood Jazz Festival is jammin’ all the way until September 20 at Hamilton Park. The Chicago Sun-Times calls it the city’s “most soulful corner.” Live jazz in the open air, local eats, spontaneous dance-offs—what more could you want? For something less mainstream but destined for TikTok fame, try the Dungeons & Dragons: The Twenty-Sided Tavern show at the Broadway Playhouse tonight. Fantasy, comedy, and audience participation not required but virtually guaranteed.Are cinematic dreams calling? The Reeling LGBTQ+ International Film Festival runs now at Landmark’s Century Centre Cinema—expect genre-bending flicks, spirited crowds, and after-parties rivaling any club night, according to festival reports.If you’re aiming for outdoorsy bragging rights, Millennium Park isn’t just for tourists. Its “Stonehenge” and “Dorit” installations add oddball intrigue to classic scenery, while Big Bus Tours serve up a hop-on, hop-off trip through hidden art spaces and food gems along the Chicago Riverwalk. For an extra ‘who knew?’ moment, try a guided Food and Walking Tour—locals rave about the deep dish and Italian beef sandwich explorations, according to TripAdvisor.Comedy Hour at Annoyance Theatre is prime for Friday night shenanigans, where Chicago comics test hilarious new material straight out of their own inside jokes and wild imaginations. Annoyance Theatre describes it as a “coliseum for local comedy gladiators.”For breakfast tomorrow, zip over to the Division Street Farmers Market, open until noon, bursting with rare finds, artisan snacks, and enough Chicago-made goods to stock a quirky Olympics-themed picnic.Pop into the National Public Housing Museum for “Living in the Shade,” which explores public open spaces—history, art, and activism meet in a space rarely explored. Meanwhile, Peppa Pig World of Play is, frankly, for your kids or your inner child, and apparently, Homeschool Days specials are a huge draw for families this week.And, to channel the spirit of sport, catch the anticipation building for the Chicago Bears’ home game next weekend (September 28 vs. the Raiders)—nothing unites Chicagoans or starts neighborhood debates quite like gridiron predictions, as local sports radio hosts will attest.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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[Fitgerald’s]. Baseball fever is still alive: tomorrow you can catch the Chicago White Sox fight the Orioles at Guaranteed Rate Field at 1:10 PM. Prefer legendary field vibes? Singles and squads are flocking to Wrigleyville for pub crawls and Cubs buzz ahead of the Cubs vs. Cardinals game on September 27 at the iconic Wrigley Field with the first pitch at 1:20 PM[Choose Chicago]. Pro tip: Get a sneaky pre-game donut at Stan’s just off Addison—locals swear they make you cheer louder.Feeling outdoorsy? Dive deep into Chicago’s green zones—the Lincoln Park Summer Nature Fest at the Peggy Notebaert Nature Museum on September 20 lets you touch frogs, meet naturalists, and learn Chicago’s wildest survival facts. Even Picasso would blink at the art, nature, and science mashup[Lincoln Park Chamber of Commerce]. For extra woodland cred, try a sensory hike at Plum Creek Nature Center (running all fall) or join the Woods Walk challenge and see if you can find a mushroom that looks like Elvis[Visit Chicago Southland].Sports-wise, pickleball is flaming hot—join the Acorn Fest Pickleball Tournament in Crete Park on September 20, and experience a crowd so pumped, their paddle skills border on the magical. If you’d rather compete with your feet, there’s a 5K Fun Run at South Holland’s Veterans Memorial Park on the same day, with finish-line local brews to celebrate[Visit Chicago Southland]. Into offbeat culture? The Second City comedy troupe dishes out improv that’ll have you cackling, sometimes at jokes you wish you’d made first[Lincoln Park Chamber of Commerce]. For secret moods, Kingston Mines delivers real-deal blues until 4AM, peppered with Chicago’s best fried chicken—yes, music and drumsticks belong together. Hungry yet? Swing by RJ Grunts for nostalgic burgers or hit Alinea if you want molecular mind-bending dining (just book ahead or offer to wash dishes for a table). Don’t miss the Clark Street Cookie Crawl—September sugar madness meets a quirky scavenger hunt in Lincoln Park, promising cookies from nearly every way-too-hip bakery in one stroll[Lincoln Park Chamber of Commerce]. Happy hour, trivia, and LGBTQ+ events pop up citywide every night. Thornton Distilling Co. runs Thursday Night Trivia tonight—you get local stories, weird facts, and the most fortifying whiskey flights in Chicagoland[Visit Chicago Southland]. Art snobs and street mural hunters, scope the ever-changing scene in Pilsen where artists update block-long murals weekly. The coffee at Café Jumping Bean is reason enough to linger; those in the know snag empanadas before noon.So—whether you’re raving at a secret show, cheering at Guaranteed Rate Field, or conquering cookie crawls, Chicago offers legendary fun for all. From music to pickleball, jaw-dropping food to late-night laughs, your next great adventure is just a L ride away.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 racing for the best deep-dish pizza slice.Music fanatics, dive into the final hours of the Lakeview East Festival of the Arts today. It runs from 11 a.m. to 7 p.m., but the party keeps rolling with food tents and live music. Local legends like Mr. Blotto and the Fox Crossing Stringband take the stage, making this an artsy, jam-packed Sunday you won’t soon forget. According to the Lakeview East Chamber of Commerce, the fest is overflowing with food, murals, and art you won’t find anywhere else on Earth.Need more sonic adventure? Gear up for the legendary Riot Fest, returning September 19–21 in Douglass Park. Green Day, Weezer, and blink-182 headline—a proper moshpit for your FOMO. Music lovers get extra points for spotting James or Weird Al Yankovic on the lineup.Sports nuts, unite! Today also means Bears vs. Lions—and Time Out Market Chicago hosts the rowdiest watch party in Fulton Market from noon to 2 p.m. Picture craft beers on tap, big screens, prizes, and gustatory touchdowns from food vendors (also, free swag). According to Time Out Market, it’s a win even if the Bears lose.Craving comedy and athletic-level improv? ComedySportz Chicago runs every Saturday at Malarkey Comedy Company, fusing theater, referee whistles, and rapid-fire improv into a sport so competitive even your local pub quiz doesn’t stand a chance.Don’t skip Soldier Field: next Saturday, September 21, the Chicago Bears clash with the Dallas Cowboys. Also coming soon, game days featuring the Chicago Fire FC for soccer fans who like their football with a side of flair. Soldier Field’s events are infamous for good vibes, tailgates, and Instagram moments even when you forget who’s winning.Cultural explorers, keep eyes out for hidden gems making waves: Pilsen’s ever-rotating open studios let you peek into local artists’ spaces. Hyde Park storefronts host pop-up jazz jam sessions, and in Andersonville, secret speakeasy bingo nights blend craft cocktails and laugh-out-loud stories from local hosts.For outdoorsy types, kayak tours off the Chicago Riverwalk reveal those picture-perfect skyline views with bonus commentary from guides who know where the turtles sunbathe and which bridges squeak the loudest. And yes, Stack Cup—the party game sweeping UK hostels—shows up in Lincoln Park picnics on warm nights, played ultra-competitively by groups of twenty-somethings.Culinary daredevils, head to Time Out Market or Fulton Market’s midsize ramen shops for bowls so spicy your eyebrows sweat off. For food with entertainment, some of the latest pop-up dinners combine improv theater with courses—think eat, laugh, repeat. Local foodies on social rave about the Filipino fusion at Kasama in East Ukrainian Village for breakfast, and you might just spot a Chicago Bull at Lou Malnati’s.From rooftop bar shuffleboard nights in River North to street art bike tours and late-night jazz under the “L” tracks, Chicago’s got wild stories in waiting, each one ready for you to make it legendary.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 noon at 30 W. Division St. You’ll find every Chicago-grown oddity from rainbow chard to spicy pickles, and perhaps someone serenading a zucchini. If you want arty inspiration with a side of history, dash to the Ravenswood ArtWalk this weekend along the Ravenswood Industrial Corridor—over 150 artists, live music, and probably a few aspiring street jugglers trying to join my imaginary Olympic Oddball Sports team.Sports fiends, rejoice! Nothing says Chicago louder than catching the Chicago Cubs clash with the Tampa Bay Rays today at 1:20 pm at Wrigley Field—where the section energy rivals a conga line after triple espresso shots. Don’t forget to roam bustling Wrigleyville before or after for pub grub, homegrown eats, and impromptu renditions of “Go Cubs Go!” For gridiron fans, tomorrow at 1 pm the Chicago Bears roar into Ford Field against the Detroit Lions, and if your fandom involves quirky rituals (lucky sausages, anyone?), this is your time to shine.Craving something immersive? Swing by The Messi Experience Chicago on Logan Blvd today for a dazzling multimedia deep-dive into Messi’s legendary career—think penalty kicks, virtual dribbling, and selfie ops galore. Over at Millennium Park, check out Franz West’s giant outdoor sculpture installations. Nothing like pondering modern art surrounded by cloud-scraping skyline selfies!Love music as much as I love spandex relay races? Chicago’s in full groove. The Lakeview East Festival of the Arts is on all weekend, mashing up live bands and 150+ artists—an essential dose of Chicago’s infectious creative energy. Looking ahead, on September 18–20, the Englewood Jazz Festival celebrates the 60th anniversary of the AACM—expect legendary jazz under the city’s late-summer skies.Food adventurers, assemble! There’s always deep-dish and Italian beef for newbies, but for a true in-the-know option, the Out of Left Field! pregame brunch near Wrigley Field amps up any game day with creative cocktails and bites you probably won’t find unless a friendly local clues you in. For exotic nibbles, the fall season is ushered in starting September 18 with Jack’s Pumpkin Pop Up near Goose Island—a sensation on TikTok where you can wander corn mazes, snack on pumpkin donuts, and snap squad pics with thousand-pound gourds.If you prefer your adrenaline cultured, the Dungeons & Dragons: The Twenty-Sided Tavern theatrical experience at the Broadway Playhouse offers tabletop fantasy shenanigans—live on stage, choose-your-own-adventure style. For night owls, secret speakeasies like those tracked by Secret Chicago promise mystery cocktails and maybe a magician or two.My fellow sports-and-music-loving thrill seekers: don’t sleep on the Instant Classics Art Show at Palette & Chisel Academy or candlelight concerts like Rings & Dragons in Wicker Park, blending fantasy scores and flickering candles for one magical night.Whether you’re chasing rooftop ping-pong, haunting Division Street for late-night vinyl, or people-watching at the Sundays on State block party next October, Chicago’s energy is contagious—it’s quirky, it’s proud, it’s constantly reinventing the adventure. Flip those socks inside out, stuff your pockets with pierogi, and get out there—Chicago waits for no one!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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 & Chisel Academy is hosting the Instant Classics Art Show all week—get inspired by fresh takes on traditional painting, and maybe find a new favorite artist.Got music on your mind? The Lakeview East Festival of the Arts returns September 13-14 on N. Broadway. Mingle with artists, catch live bands, and snack on street eats that’ll fuel your funky dance moves. Next week, Lady Gaga brings her Mayhem Ball tour to the United Center on September 15, 17, and 18, so snag tickets if you want the full monster experience—and if you dress in something wild, you might even trend on social by Monday morning.Sports nuts, wriggle your way to Wrigley Field! The Cubs battle the Tampa Bay Rays September 13 and 14, classic ballpark vibes guaranteed. Or embrace local rivalry and root for UIC Flames Volleyball on September 12 or snag live college soccer at Loyola on September 15. For grassroots grit, hit up the El Grito 5K Family Run/Walk in Little Village on the 14th, then join the citywide Mexican Independence Day parade with music, food, and the kind of energy that could power a fleet of hot dog carts.Feeling extra quirky? Today at Broadway Playhouse, dive into Dungeons & Dragons: The Twenty-Sided Tavern—a full fantasy experience with audience participation that attracts every creative costume in Chicago. If improv is your jam, the Annoyance Theatre hosts Comedy Hour tonight, where local comics test out new material and possibly, questionable hairstyles.For outdoorsy escapades, join the free Chicago Greeter InstaGreeter Walks touring either the Riverwalk (meet at the Vietnam Veteran’s Memorial at 11:30 AM) or the Loop (meet at the Chicago Cultural Center), both perfect for discovering hidden murals and secret skyline selfies only locals know. If you prefer nature and science, the Peggy Notebaert Nature Museum’s “By A Thread: Nature’s Resilience” exhibition is open today and is basically my Olympics for butterflies.Food lovers, you can score citywide deals with the Choose Chicago Pizza Pass through December. Try slices everywhere from classic Lou Malnati’s to cult faves like Piece or Paulie Gee’s. For the freshest flavors, the Division Street Farmers Market runs this morning until noon—so grab some local honey, edgy jams, and an impossible number of apples.If you want more culture, the Illinois Holocaust Museum’s Experience360, and the McAninch Arts Center’s “Hokusai & Ukiyo-e: The Floating World” (with 70 Edo-period art pieces!) are open and trending—Dr. Who fans, time travel is not required.Lastly, for those who collect quirky stories, check out The Messi Experience Chicago, an interactive multimedia exhibit inspired by the world’s soccer legend, and feel like you’ve scored a goal—without sweating.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 Dungeons & Dragons: The Twenty-Sided Tavern at Broadway Playhouse at Water Tower Place tonight and all week—improv, role-play, dragons, and audience chaos collide right in the heart of the city. Theater nerds, fantasy fans, and even those who think dice are just for Yahtzee will love it.Music is living large in Chicago this September! Experience a truly wild mashup at Wicker Park Lutheran Church with the Candlelight: Rings & Dragons concert—think The Lord of the Rings and Game of Thrones but with live strings, candlelight vibes, and plenty of dramatic musical fantasy all through November. If you hear someone humming the theme from Westeros in the grocery store, blame me.Attention sports maniacs: The Bank of America Chicago Marathon is barreling through the city on Sunday October 12, and the best spot to watch the action is mile 5 near Lincoln Park—join the Shamrock Shuffle Cheer Zone, wave flags, and grab brunch at Café Brauer or The Vig before rolling over to Lincoln Park Zoo to high-five a hippo. If you’re itching for competitive energy tonight, catch the Chicago State Cougars battling Southern Illinois at 6pm, streaming on ESPN+. And there’s always epic pro sports at Wrigley Field, United Center, or Soldier Field—nothing says “iconic” like a Chicago Bears game or a flying nacho at a White Sox match.For locals who want some real quirk: swing dancing erupts at Gallagher Way (next event is September 22, so mark your calendar)—whether you’ve got two left feet or fancy yourself a reincarnated Fred Astaire, you’ll meet wild characters and maybe discover your next obsession. Hit up pop-up foodie experiences downtown, where trendy chefs are pushing flaming ramen and neon-lit churros.Art lovers and curious rebels should sneak into street art alleys in Pilsen, tour the murals, and pause at Thalia Hall for spontaneous indie gigs. Social media’s blowing up with posts from the immersive Van Gogh Exhibit downtown—yes, you can finally waltz through a sunflower field without getting kicked out for trespassing.Finally, those truly “in the know” sneak to hidden speakeasies disguised as laundromats, like The Laundry Room, where cocktails arrive with a magic trick and bartenders tell outrageous Chicago ghost stories. Or hunt rooftop views at Cindy’s above the Chicago Athletic Association—grab a quirky craft brew, gaze out at Millennium Park, and try not to spill your drink while doing your best marathon runner impression.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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI
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 epic bites from over 50 vendors, bask in live music, people-watch, and make every snack count for personal glory—whether you’re a deep-dish devotee or a hot dog heretic. Still hungry? Pop onto the city’s South Side for the Palos Heights Farmers Market, open Wednesdays till October with stand-up local produce and a welcome lack of kale snobbery.Craving something outlandishly sportsy? I have good news, listeners: you can swing by Wrigleyville and soak in true Chicago baseball energy—even if the Cubs are away, Wrigley Field’s neighborhood delivers post-game revelry all week with legendary bars, rooftop views, and oversized nachos doing gravity-defying acrobatics.Sunday, September 7, brings live music to Wicker Park where Kenny Lane lights up Wicker with a free outdoor concert—yes, dance like nobody’s livestreaming. If you like your music candlelit and classy, Stan Mansion hosts a raved-about Candlelight Tribute to Adele, bathing you in both “Someone Like You” and about two million LED glows.Chicago’s arts scene is basically an Olympic sport of creativity right now: The Palette & Chisel Academy is hosting the Instant Classics Art Show all week, where six femme artists remaster tradition—talk about brushstroke bravado. Meanwhile, Millennium Park is transformed by sculptor Franz West’s monumental Stonehenge and Dorit installations—perfect backdrops for your next viral TikTok handstand.Theatrical souls, Dungeons & Dragons: The Twenty-Sided Tavern runs at Broadway Playhouse, inviting you to role-play in a tavern with more surprises than a rogue’s spellbook. Babes With Blades Theatre brings you sword-swinging action at their “Fighting Words Festival” through September at the Bramble Arts Loft.Want to keep that athletic edge? Hit the Swap-O-Rama Flea Market for vintage finds that’ll upgrade your post-pickleball streetwear, or root for UIC Flames men's soccer at the Flames Field on September 7 as they take on Wright State—trust me, the passion rivals World Cup fever.Edgewater Music Fest fires up at Broadway and Thorndale Sunday for still more tunes, foods, crafts, and local flavor. Get there to find your new favorite band or at least a festival hat that makes you 30% cooler.For the true offbeat explorer: schedule a Peotone Windmill tour Sunday, just outside the city, to see a real working windmill in action because "giant rotating historical objects" is my kind of niche hobby. Or trade sunlight for spotlights at The Messi Experience in Logan Square, where you can channel your inner fútbol legend in an immersive, multimedia soccer journey worthy of social feeds worldwide.Feeling competitive? Test your mettle at Sand Ridge Nature Center in South Holland with nature walks that’ll let you pretend your step count is an Olympic record.That’s your adventure map through secret foodie beats, jaw-dropping art, sports swagger, and music-fueled dance breaks—a full menu of delight whether you’re born and raised, fresh to the Windy City, or simply hunting for those FOMO-defying stories to humblebrag about at brunch. 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.For more check out https://www.quietperiodplease.com/and make sure to jump on these great deals https://amzn.to/3V0gjPtFor more on Oly check out https://www.instagram.com/olybennet/This content was created in partnership and with the help of Artificial Intelligence AI