Welcome, listeners, to Things to Do in Chicago—your daily dose of windy city adventure with me, Ollie Bennet! It's Friday, October 24, 2025, and Chicago is waking up to crisp, fall perfection. The air is brisk—morning temps in the low 40s, climbing to the low 50s under a mix of sunshine and scattered clouds. No rain, no snow, just pure autumn glory. There's a freeze warning in some areas, so if you're headed out early, grab your funkiest sweater—this is the city where fashion meets frostbite.

Now, the vibe out here is pure energy. The streets are buzzing with pre-Halloween anticipation, the aroma of pumpkin lattes wafting from every corner café, and the riverwalk sparkling under those cool blue skies. Let’s get you plugged into Chicago’s epic calendar for the day!

First up, comedy fans are in for a treat tonight as Nate Bargatze brings his Big Dumb Eyes World Tour to the United Center. According to The Atlantic, Bargatze is “The Nicest Man in Stand-Up”—and judging by Chicago’s ticket frenzy, the city’s ready for a night of gut-busting laughter. Show starts at 7PM, with a pre-party kicking off at 5PM—private entry, DJ sets, free cocktails, exclusive merch. To get there, you’ve got CTA buses, Blue, Green, and Pink Lines all rolling and plenty of parking if you're still rocking that vintage 2002 Civic.

But wait, culture vultures—slide over to the Chicago Cultural Center tonight for DCASE's Under the Dome. Local musicians Rich Robbins and Demetruest headline live under the dazzling Tiffany glass dome, with a Chicago Fair Trade clothing swap happening alongside. No ticket needed, doors open at 5PM, and it’s an all-ages bash—so even grandma can catch the groove.

If you’ve got a wild child with you (or you are one yourself), Lincoln Park Zoo is hosting Adults Night Out: Howl-o-ween. This after-hours creature feature is a one-of-a-kind night for grownup goblins—think zoo cocktails, haunted habitats, a lot of howling at the moon.

Craving music? Don Broco lays it down at House of Blues at 7PM, and Schubas and Lincoln Hall explode with indie and local acts all weekend. The Infinite Wrench at the Neo-Futurist Theater promises 30 rapid-fire plays in 60 minutes—true Chicago-style artistic chaos.

News flash—Chicago’s transit system is running smooth with extra service for big event nights. If your taste buds want adventure, rumor has it there’s a new taqueria opening in the West Loop, featuring not just tacos, but a guacamole bar. Yes, Chicago knows how to win hearts.

For today's must-dos: cruise Millennium Park for leaf-peeping and selfie central under The Bean, check out the farmer’s market at Daley Plaza until 2PM—stock up on apples, cider, and stories from folks who know every secret about the city. And if you’re a true offbeat-sports seeker, ask around about the legendary Chicago Squash Ball—an obscure game played underground since 1985 where the only rule is chaos. If you find it, report back—I’ll trade you three fun facts and a signed hot dog napkin.

Here's a fun local tip: “The Loop” isn’t just a name—it refers to the circuit of elevated train tracks downtown. If you ride a full loop, some folks claim you gain temporary superpowers. Effects may vary. Bragging rights, guaranteed.

Looking ahead—tomorrow Gallagher Way explodes with the Pumpkin Party from 1 to 5PM. Costume parade, pumpkin crafts, and haunted hilarity for all ages. And with the Chicago International Film Festival rolling all weekend, tune in tomorrow for more wild picks, celebrity sightings, and hidden gems.

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Welcome, brilliant listeners, to another adrenaline-pumped, thrill-packed episode of Things to do in Chicago! It’s Thursday, October 23, 2025, and I’m your globe-trotting, high-fiving, sports-obsessed pal Oly Bennet, here to make your day as lively as a Wrigleyville bar on game day.

Let’s dive right in: Today, Chicago is buzzing like a marathon runner who just chugged three espressos. Crisp autumn air has the city wrapped in electric sweater weather, but the sun’s out, and the energy is all go. If you’re into a little cloud drama with your plans, you might get those dramatic Lake Michigan skies, straight out of a sports movie montage.

Now cue the wild mix of today’s events—Chicago’s always serving something for everyone. For job-seekers or folks craving new horizons, the Congress Plaza Hotel is hosting the Chicago Job Fair from 11 till 2. This is your shot to network like a pro and maybe land a gig before your next hot dog according to Eventbrite.

Cultural explorers, polish those jazz hands and jog down memory lane: The Copernicus Center is celebrating with David Meulemans’ 65th Birthday Benefit for Chicago Cabaret Professionals tonight. It’s got music, witty banter, and all the showbiz glitz you’d expect from a city that gave birth to improv legends, as highlighted on the Copernicus Center’s site.

Love a good market and the smell of fresh produce with your midday hustle? The Daley Center’s famous Farmer’s Market is open till 2 p.m. Squeeze some apples, do the tomato two-step, or just soak up local flavors right downtown according to the Daley Center events calendar.

Looking for a unique challenge with your Thursday? Reggie Hathorn’s Fragrance Making Class is happening at 1 p.m.—test your sniffer, concoct your own scent, and maybe invent Eau de Deep Dish, as Eventbrite lists in its quirky calendar.

If laughter is your superpower, the United Center is about to host Nate Bargatze’s Big Dumb Eyes World Tour—the man’s got jokes sharper than the wind off Navy Pier. Arrive early to score pre-show party perks and exclusive merch. United Center has details for all you comedy lovers out there.

Now, hot off the Chicagoan press: The city is abuzz with new eats in West Loop—rumor has it, a ramen spot so authentic it’ll have your chopsticks doing a touchdown dance. Transit agencies say Blue Line trains are running on time today, which in itself is a minor miracle worth a cheer.

Still craving adventure after hours? Take the El north to Andersonville for a stroll—it’s all local boutiques, Swedish bakeries, and that sort of indie charm that makes even a seasoned globetrotter like me want to linger. Or go wild and try the Green City Market for autumnal treats downtown; the cider donuts are life-changing, according to Chicago on the Cheap’s event calendar.

Here’s an Oly Bennet fun fact: The iconic Chicago “dibs” tradition—staking claim to a parking spot with offbeat objects—kicks into high gear every time the weather turns. If you see a barstool, lawn chair, or even a flamingo squatting in a snow-cleared spot, it’s sacred territory. Respect the dibs, folks!

Don’t forget, this weekend’s bringing the Pumpkin Party at Gallagher Way, the Boo! at the Zoo bonanza, and Halloween haunts everywhere from Lincoln Park to Wrigleyville. Tomorrow’s episode will feature more tricks, treats, and epic ways to chase the thrills of the world’s quirkiest city.

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Welcome, adventurous listeners, to “Things to do in Chicago”—powered by Oly Bennet, your global passport to the planet’s most offbeat happenings, and today I’m tossing the Chicago playbook your way with a hearty high five. It’s Sunday, October 19, 2025, and if you haven’t noticed, Chicago is buzzing like a field goal in overtime! Cloudy skies are keeping temps cool, giving everyone an excuse to break out those fresh fall layers and fuel that café-hopping spirit.

First up in today’s Chicago saga: the Windy City is serving a literal marathon of events. For you early risers, the Chicago Lighthouse’s Rise to Shine 10K/5K/1M Run & Walk took over the streets at 8 AM—run for charity, stretch your legs, or, let’s be honest, stand on the sidelines with a coffee and cheer like it’s the sports championship of the year. Prefer cheering on art over athletes? The citywide Open House Chicago festival wraps up today, so it’s your last chance to sneak into dozens of architectural hidden gems that are usually locked up tighter than a hockey goalie’s gloves. Explore legendary spaces from the South Loop up to Uptown—snap a selfie, drop a jaw, repeat.

Culture vultures, your wings are needed at the West Loop Contemporary Fine Art Expo’s grand finale, bursting with new works from the city’s hottest up-and-coming artists. If tunes get your heart racing faster than a last-second buzzer beater, tonight at the Epiphany Center for the Arts offers a soulful set by Ken Fobs at 6 PM followed by a Candlelight Tribute to A.R. Rahman at 8:30. Now THAT’S a double-header.

Families and fun-lovers, Midtown Athletic Club is hosting their annual Fall Fest: think bouncy houses, pumpkin decorating, and enough seasonal snacks to keep you powered up for the world’s quirkiest sack race championships. If your tiny humans still have energy, Abbeye Farms’ Pumpkin Daze Fall Festival keeps the autumn charm alive with hayrides and a mega corn maze just beyond the city.

On the ticket of big city excitement, The Book of Mormon brings Broadway-level laughs to CIBC Theatre—catch their last show tonight. Feeling a bit spookier, Rocky Horror Picture Show’s 50th Anniversary Spectacular rolls into The Chicago Theatre. It’s interactive, it’s electric, it’s… definitely one for the story vault.

Let’s shoot over to local buzz—Chicago just welcomed new restaurants in River North serving Detroit-style pizza that’s so thick, you could use it for shot put practice. The L reroutes around the Loop are done for the weekend, so transit riders have full reign—slide onto the Red Line and chase the action from Sox Park to Lincoln Park.

Craving the ‘only-in-Chicago’ experience? Wander out to the DANK Haus German American Cultural Center’s open house for a stein or some bratwurst, or stroll by the lakeshore and catch wind surfers who look like they’re auditioning for the city’s next zany sporting league. Looking for the underdog? Hunt down one of those classic neighborhood jazz brunches, where the mimosas flow as smooth as the trumpet solos.

Chicago always holds a trick up its sleeve: Did you know the city’s alleys total nearly 1,900 miles—more than the distance from Chicago to Miami? Only here could you find postmodern masterpieces (and a secret bocce court) by just wandering off the main drag. So trust your feet, trust your gut, and don’t be surprised if you stumble into your new favorite haunt.

Keep your calendars handy, because tomorrow, the Chicago Architecture Center rolls out encore tours, and don’t miss the golden-hour live music at Epiphany Center’s Café Bar—hello, half-price wine and acoustic vibes!

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Welcome, adventurous listeners, to Things to Do in Chicago with your intrepid host Oly Bennet, scouring the globe for the wildest competitions—but today, we’re right here in the heart of the action on Saturday, October 18, 2025! Pull on your wackiest hat and tighten those shoelaces: the Windy City’s vibe is absolutely electric with a cool fall breeze, a touch of Halloween mischief in the air, and a whopping dose of cultural fireworks.

Let’s zero in on the city’s pulse today. Step outside, and you’ll feel that crisp October zing—a perfect day for urban adventures or a mad dash to the nearest dance floor. And speaking of floors, it’s a full house everywhere you look, with parties, parades, and performances lighting up the city like a Diwali sparkler.

What’s on the docket for today? If you’ve got a costume that’s been dying to see daylight, don’t miss Chicago’s largest Halloween parade, Arts in the Dark, strutting down State Street tonight from 6 to 8 p.m. This is not just any parade—we’re talking giant glowing puppets, wild floats, local artists busting every creative move, and about a hundred thousand open-mouthed spectators. It’s so legendary USA Today rates it among the world’s best Halloween parades, so get your glow sticks ready.

But maybe your celebration style leans more “Festival of Lights” than “Monster Mash”? Lore nightclub is throwing the city’s biggest Diwali Glow Party starting at 10 p.m. with top DJs, Bollywood beats, rooftop views, neon decor, and a dress code calling for your flashiest saree, kurta, or clubwear. Pack your stamina, because this party is set to go off like a box of fireworks in a candy store.

For my family squad or fans of heartwarming nostalgia, the Chicago Children’s Museum debuts “Take Care with Peanuts: The Exhibit” today. Step into the world of Charlie Brown and Snoopy with interactive activities around self-care, empathy, and saving the planet. It’s smiles for days and perfect for Peanuts lovers big and small.

Concert fiends, prepare your vocal cords. The United Center hosts the epic Brandy and Monica: The Boy Is Mine Tour tonight, joined by Kelly Rowland and Muni Long. This is a historic, once-in-a-generation R&B blowout and a must for serious music lovers. Meanwhile, the Civic Opera House is staging “Coco in Concert,” where you can experience Pixar’s smash hit live with a full orchestra—bring tissues for tears of joy.

The city’s not just about spectacles—there’s high culture on tap, too. Chicago Architecture Center launches Open House Chicago this weekend, turning the whole city into a backstage pass for architecture geeks and urban explorers. Wander into beautiful historic mansions, cutting-edge skyscrapers, and spaces usually off-limits. Free, citywide, and only two days a year!

If you’re craving street eats, Jackson Plaza’s Chi Food Truck Fest rolls up with flavors from around the world, while the weekly Farmer’s Market is perfect for snagging local treats.

Now, some handy news to grease your adventure engines. Transit is humming along, and the city’s gotten a shiny batch of new hybrid CTA buses, making zipping between neighborhoods even smoother. For foodies, keep your eyes peeled for the grand opening of Banh Mi Galaxy in Wicker Park—word is, their lemongrass tofu banh mi is the Vietnamese sandwich Chicago never knew it needed.

Oly’s tip of the day: when the crowds swell or you need to zip between events, hop on the Green Line—fast, efficient, and perfect for parade or night-out hopping. And for a truly hidden Chicago treat, detour to the quaint Giddings Plaza in Lincoln Square—bring a coffee, soak up the local color, and catch some fabulously quirky street music.

Before you dash off in a blaze of Diwali neon or Halloween glitter, get ready for tomorrow’s encore: Open House Chicago continues, Lion King roars on at the Cadillac Palace Theater, and rumor has it there’s a pop-up pie-eating contest in Wicker Park that could go down in sports history—just my kind of event.

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.

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Welcome, adventurers, to Things to Do in Chicago! Today’s Friday, October 17, 2025, and Oly Bennet reporting for duty—fueled by deep-dish pizza, Lake Michigan breeze, and an obsession with everything weird, wacky, and wonderful in the Windy City. Let’s catch today’s vibe: the autumn air is crisp, the lakefront is buzzing with Friday-feels, and if you’re lucky, you might even spot locals perfecting the ancient sport of dodging falling leaves on Michigan Avenue.

Chicago’s got its game face on for fall. Festivals pump energy into every neighborhood—even the pigeons seem peppier. What’s setting the tone? According to Patch.com's event calendar, there’s music, movie magic, and family fun splattered all over town, perfect for everyone from culture buffs to sports maniacs and giggle-seekers.

Amping up for tonight, here’s some top-tier Chicago action to launch your weekend:

Comedy takes center stage at The Chicago Theatre, with Morgan Jay charging in for two shows on The Goofy Guy tour—7 and 10 pm. Expect a riot of laughs, maybe even some tunes, and plenty of joyful mayhem. Don’t forget to check your digital tickets and bags—The Chicago Theatre is a stickler, but they’re committed to maximum fun.

Classical and cool collide at the Studebaker Theater where the Camerata Chicago Orchestra presents Peter and the Wolf at 7:30 pm. Perfect for families or anyone craving an epic soundtrack to autumn.

If music with a modern twist is your jam, Epiphany Center for the Arts rolls out the Golden Hour starting at 5 pm (half-priced wine, anyone?), followed by Future Nobodies with Ghost Days and Twin Ion Engine at 8 pm—a doubleheader of dreamy post-punk and nostalgia-fueled indie rock. Arrive early, catch some art, then drift into sonic bliss.

Night owls, rejoice: Rooftop Cinema Club Fulton Market is running a movie marathon—kick things off with Pride & Prejudice at 5 pm, cue up Scream (1996) at 7:55, and round things out with Friday the 13th (1980) at 10:45 pm. Horror, romance, and skyline views.

Sports fans, United Center hosts a classic: Chicago Blackhawks vs. Vancouver Canucks at 7:30 pm. Expect roaring fans, fast ice, and maybe a hot dog duel that would make Joey Chestnut sweat.

For family fun, the Nights of Little Italy at the Albert kicks off at 9 am with a feast of Italian American cuisine—good luck resisting the cannoli—or swing by Sonny Acres Farm’s Fall Festival in West Chicago for pumpkin picking, hayrides, and haunted barns running through October 30.

In the city news blitz, the 61st Chicago International Film Festival is in full swing, lighting up screens across town until October 26. New restaurants pop up like wild mushrooms in River North and Fulton Market, so try a new spot before the crowds discover it. Public transit updates: the CTA is running regular schedules, but the Red Line might be performing its own Olympic event—train leap-frogging—so leave a little early.

Looking for must-do activities? Stroll Millennium Park (the Bean: still the best spot for group selfies and impromptu tourist Olympics), try a kayaking session on the river if you dare, or catch late-night jazz in a tucked-away club. Oly’s explorer tip: sneak into the Art Institute’s Modern Wing after lunch when crowds ease—bonus cultural karma and some of the world’s best people-watching.

Chicago was nearly named "Lake Michigan City"—imagine cheering on the Lake Michigan Bulls! Let that fun fact fuel your party trivia arsenal.

Don’t miss what’s next: tomorrow brings the magical Arts in the Dark Parade on State Street—think glowing floats, larger-than-life puppets, and more sparkle than a disco marathon. Harvest festivals, film screenings, and rooftop revelry are ready to roll, so tune in for all the details and a fresh batch of wild Chicago happenings.

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.

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Hey there, adventurers Welcome to 'Things to do in Chicago' It's October 16, 2025, and the Windy City is buzzing with excitement. While the weather is crisp and perfect for fall, the city's vibe is all about culture, music, and a dash of spooky fun as Halloween approaches.

Today, you can catch the Chicago Bulls vs. Minnesota Timberwolves in a preseason game at the United Center. Music lovers, don't miss the Ear Taxi Festival's Composer Showcase Featuring Lakeshore Rush, premiering new works by Illinois composers. If you're in for some laughs, Iliza Shlesinger is wrapping up her comedy stint at The Chicago Theatre, but Straight No Chaser is gearing up for their Holiday Road Tour later this month.

For local news, Chicago is always buzzing with new restaurant openings and public transit updates, so keep an eye out for those. If you're looking for something unique, head over to Cantigny Park for a colorful fall foliage experience.

Here's a local tip: use the Ventra app for easy public transit navigation. And did you know that the Chicago Theatre is one of the most historic venues in the city? It's worth a visit just for its architectural grandeur.

Tomorrow, be sure to check out the Pleiades Improv Jam at the Ear Taxi Festival. It's going to be a blast And don't forget, the spooky Halloween fun is just around the corner.

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.

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Welcome listeners to Things to Do in Chicago! This is your guide to everything that’s making the Windy City sparkle today—Sunday, October 12th, 2025. I’m Oly Bennet, your globe-trotting, sports-loving, adventure-chasing host, here to serve up the quirkiest happenings and wildest vibes Chicago has to offer.

Let’s set the scene: Chicago is buzzing this Sunday with temperatures kicking off in the brisk mid-50s, perfect weather for lacing up your sneakers, grabbing a jacket, and exploring the city. The energy? Absolutely electric, because the one and only Bank of America Chicago Marathon is back! From Grant Park to Chinatown to Goose Island, runners from every corner of the planet are pounding the pavement while fans line the streets with cowbells, signs, and contagious enthusiasm.

If races aren’t your thing, Chicago is never short on adventure. How about immersing yourself in the dazzling world of Urban Visionaries: Chicago Fashion Week? Tonight kicks off with High Octane Couture at the Chicago Car Collective, merging luxury fashion, supercars, champagne, bold designers, and the smell of fresh cigars—talk about a runway with horsepower!

Craving an artistic twist? Head to Navy Pier’s Aon Grand Ballroom for the Black Girl Art Show, a vibrant, empowering six-hour celebration of Black women artists. Think live performances, immersive installations, and way more sparkle than your average Sunday.

Love live music or prose? Over at the Epiphany Center for the Arts, it’s “Bar For Bar – A Celebration of Hip Hop & Poetry.” Rappers, poets, and lyricists are gracing the stage at 7pm—free entry, good vibes, and the chance to say, “yeah, I heard that performer way back when!”

And families—looking for some autumn magic? Zip out to Sonny Acres Farm’s legendary Fall Festival in West Chicago. It’s pumpkins galore, hayrides, giant slides, a petting zoo, and, for the brave, haunted barns and hayrides after dark. Guaranteed sugar rush recommended by Chicago’s dentists.

Sports fans—could I forget you? The Bulls are dusting off their jump shots in a preseason showdown against the Milwaukee Bucks at United Center at 6pm. If you hear the roar of the crowd, dive in for some hardcourt drama.

Let’s fast break into today’s local news: According to the Sun-Times, the CTA’s Red Line is running full service after last night’s maintenance—so hop around town without a hitch. Chicago’s dining scene is still sizzling: Timeout Chicago spotlights the grand opening of “Wild Onion Kitchen,” a funky all-day diner in Logan Square that’s already drawing lines for its pierogi omelets and pecan pie pancakes.

Now, a true Oly Bennet pick—if you want a splash of hidden magic, check out the free “Afternoon at the Art Museum” at MCA Chicago, starting at 5pm. Locals know that Free Museum Sundays are golden: less crowded and perfect for an impromptu art adventure.

Local tip: If you’re marathon-bound, grab a spot near Pilsen around mile 19 for the liveliest music, Talavera tile art, and the most contagious high-fives you’ll ever experience. It’s where the soul of the marathon truly shines.

Before I dash, some teases for tomorrow: The city glows with post-marathon parties, River North hosts a craft beer crawl, and the DuSable Museum is offering another free day for Chicagoans hungry for some history.

Thanks for tuning in! Set your alarms and bring your curiosity: we’ll be back with more Chicago action, oddities, and epic tales tomorrow!

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.

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Welcome, adventure seekers, to Things to Do in Chicago with your trusty guide Ollie Bennet—globe-trotter, certified sports nut, and connoisseur of the strange and wonderful! It’s Saturday, October 11, 2025, and Chicago is buzzing with fall energy—sunshine overhead, a crisp breeze off Lake Michigan, and enough events to make your head spin like a deep-dish pizza at full throttle.

Today, Chicago is showing off its festival swagger, and the weekend is supercharged with everything from mouthwatering bites to mind-bending escape rooms. I just spent the morning people-watching on Lincoln Avenue, where the aroma of fresh coffee, sizzling bacon, and the faint sound of indie bands tuning up marks the return of Lincoln Brunch Fest. Imagine morsels from Chicago’s best brunch spots, live tunes, family-friendly games, and the kind of cheerful chaos that only this city can dish up, all happening right now at 2900 N. Lincoln Ave, as spotlighted by Eventeny.

Art fans, head over to The WasteShed for the wild and eco-friendly Soda Can Mosaics workshop hosted by Chicago artist Norma Rios-Sierra. You’ll snip, snap, and sticker your way into soda-can glory, leaving with a one-of-a-kind mosaic and a newfound appreciation for upcycling. Love a bit of night magic? Rooftop Cinema Club is screening La La Land and 500 Days of Summer tonight, so bring a blanket and experience movie musicals and heartbreak comedies under the sparkling city skyline.

For pop-culture junkies, Lisle is throwing down at Hallow-Fest, the region’s two-day anime and gaming convention, complete with cosplay, shopping, and endless tournaments. Looking for something truly unique? Center on Halsted is the place to be for QueerQuest. Honored by the United Nations, this celebration of Black, brown, and queer identities features a mind-boggling quantum escape room, wellness spaces, science talks, hammocks, tea lounges, and performances ranging from drummers to healers. According to Fox 32 Chicago, you don’t need to know quantum physics, but bring your curiosity!

Chicago’s kid-friendly side never takes a day off. The Griffin Museum of Science and Industry’s Science Works event is packed with hands-on experiments and discovery—perfect for little explorers. Prefer music? The House of Blues is alive and riffing with live blues shows all evening long. Head up to Norris University Center for “Street: Photographs by Ann Kogen,” a daylong exhibit capturing urban life at its rawest.

Now, what’s the word on the street? According to Patch and local theater guides, downtown arrivals today should check transit updates before heading in—weekend service changes on the Blue Line might add some minutes to your trip. The weather’s treating us all to classic Chicago autumn: jacket weather, but T-shirt optimism. And for foodies, rumor has it that a new ramen joint just opened in West Loop—perfect for slurping up after your rooftop movie or a stroll through Millennium Park!

Here’s your local tip: the Daley Center’s farmers market is open this morning—come early, get an apple cider donut, and claim a spot among the regulars. And if someone offers you “Chicago mix” popcorn, accept no substitutes—it’s a wild, delicious blend of caramel and cheese. Only in Chicago does sweet-and-savory popcorn spark as much debate as our pizza or baseball.

Coming up tomorrow, Navy Pier welcomes the Black Girl Art Show, a stunning showcase of Black women artists in the Aon Grand Ballroom—if you need another reason to linger by the lakeshore. Open House Chicago is just a week from now, so stay tuned for tips on how to peek inside some of the city’s most jaw-dropping buildings.

Thanks for hanging out with me, Oly Bennet, as we leapt through Chicago’s wild weekend scene. Tune in tomorrow for what’s next, and remember: in this city, there’s always more to discover.

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.

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Welcome, listeners! Oly Bennet here, your globe-trotting, tennis-ball-chasing, ferret-racing enthusiast guiding you through today’s episode of “Things to do in Chicago,” recorded on Friday, October 10, 2025. Chicago is serving up classic brisk autumn vibes—so grab your coziest jacket, because the cool breezes off Lake Michigan are sweeping through neighborhoods as Halloween decor battles for dominance on every stoop, and orange leaves attempt gymnastics from the skyline to the streets.

The city’s current energy is a swirling mix of pumpkins, live music, and pure Midwestern anticipation. According to Third Coast Review, today’s forecast predicts falling temps, so bundle up if you’re venturing outside. Chicago, you marvelous, multitasking metropolis: tonight, you’ve got everything from soulful concerts to monster movie marathons and wild festivals, ready to catapult you into a weekend of adventure.

Let’s launch into five sizzling events lighting up today:

For the musical souls, the Grammy-winning Laufey lands at United Center tonight with her blissfully jazzy “A Matter of Time” tour. As if that’s not enough, Suki Waterhouse will sweep you off your feet as the opener! For those who prefer their music with a side of chicken tenders and air guitar, the House of Blues fires up their Live Blues night—tonight starting at 5PM—where the riffs are hot and the crowd is always in full swing.

Movie magic more your style? ChiTown Movies transforms Pilsen into a retro drive-in paradise, screening Halloween essentials like “Hocus Pocus” at 7PM and “Beetlejuice” at 9PM. It’s BYO-screams and snacks! Families and pumpkin-obsessives, Jack’s Pumpkin Pop-Up in West Town also opens its gates, inviting you to get lost in a corn maze, compete in carnival games, and pose with more gourds than a squirrel can count.

Culture seekers, don’t miss “Dead Presidents” at All Star Press or the immersive wonders at WNDR Museum. And tomorrow, the glass pumpkin patch invades Morton Arboretum with jaw-dropping sculptures to shatter your expectations of “seasonal décor.”

On the local news front, notably, several new restaurants have recently flung open their doors—check local sites for the latest on this week’s food scene. The CTA reports updated Blue, Green, and Pink Line service for concertgoers heading to United Center; don’t forget, the arena’s Uber Zone at Madison and Wood makes rideshares snap-crackle-pop easy, and parking discounts are available in advance.

Public transit is running smoothly today, and rumors say yet another coffee shop just debuted in Logan Square—so if you need to caffeinate before your next dance-off (the sidewalk kind), you know where to go.

Now, for must-dos: stroll Maggie Daley Park for views and playground hijinks, and don’t miss the Garfield Park Conservatory for steamy gardens that’ll chase away any shivers. If you want the inside scoop for city newcomers: locals know that the Clark Street hot dog stands deliver the best post-midnight fuel after your exploits, and the fastest way to blend in is to loudly debate deep-dish vs. thin crust within earshot of at least three strangers—it’s practically a civic duty.

Fun fact: Chicago’s Maxwell Street Market, running since 1912, is still the ultimate spot for thrift hunting and taco overload—catch it this Sunday and tell them Oly sent you.

Looking forward: tomorrow launches the legendary Oktoberfestiversary at Begyle and Dovetail Breweries—live music, rivers of brews, and dog-friendly fun! For the lowrider fans, Navy Pier rolls out the “Slow & Low Festival” tomorrow, promising dazzling chrome for all.

Don’t miss tomorrow’s show, where I’ll dive into zombie runs, secret speakeasies, and a festival dedicated entirely to rubber chickens. 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/

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Welcome, listeners, to Things to Do in Chicago! It’s Thursday, October 9th, 2025, the air in the Windy City this morning is brisk, the leaves are on full Technicolor display, and there’s an electric buzz radiating across the city. Chicagoans are bundled up in their team scarves, oat-milk lattes firmly in hand, and whether you’re a local legend or a visitor hoping not to look too lost on the L, you’re in the right place for today’s quirkiest happenings.

The city is in full autumn swing and the event calendar today is jam-packed with something for everyone. According to Chicago on the Cheap, Chicago Fashion Week is turning the Magnificent Mile into a catwalk of outrageous style, while the Destinos Latino Theater Festival brings drama, laughter, and deeply heartfelt stories from across the Americas to venues citywide. For art lovers, the Chicago Architecture Biennial is popping up with mind-bending installations—if you’ve ever wanted to see a building made out of recycled pizza boxes, now’s your chance! And for families, there’s the Night of 1,000 Jack-o’-Lanterns glowing at the Botanic Garden and Fall Fest at Lincoln Park Zoo, featuring pumpkin picking and a Ferris wheel that makes even grown-ups squeal. Lovers of theater and epic tunes take note: The Book of Mormon is raising eyebrows and splitting sides at the CIBC Theatre this week, while the Chicago Theatre itself hosts comedian Jimmy Carr tonight at 7pm.

Cultural explorers can check out the opening of Silver Lining: The Prints of Derrick Adams at the Newberry Library, plus pop by the Art Center Highland Park for their Friday night community art jam. If you want to mix advocacy and education with your evening, head to the West Chicago Public Library for the Know Your Rights Workshop hosted by Immigrant Solidarity DuPage, starting at 6pm.

Now, let’s talk city buzz. First up, in the world of eats and treats, whispers from the local foodie circuit are all about a grand opening in River North—Giddy Up Dumpling Bar is serving up wild fusion creations and late-night bao. Meanwhile, public transit riders, take note: the CTA is piloting a contactless payment upgrade on the Red Line, which means you can now tap your way onto a train with your phone, Magic Mike style. Plan ahead, though, because some service delays are expected during this rollout, so give yourself a little buffer and pack a granola bar.

Your must-dos for the day? Don’t leave without taking a stroll along North Park Village Nature Center, where the trails are lined with crunchy leaves and city squirrels plotting their next grand heist. Sneak over to Logan Square for an unmarked, underground comedy open mic—just follow the sound of laughter and the faint scent of Chicago dogs. If you’re up for an evening thrill, hit the Chicago Botanic Garden for an after-dark pumpkin spectacle: 1,000 glowing jack-o’-lanterns and a chance to judge whose pumpkin smile is more menacing—your neighbor’s or the one carved by a world-class artist.

Here’s an Oly Bennet tip: if you want to see Chicago at its most local, grab a late breakfast at a neighborhood diner and sit at the counter. You’ll hear more about the Bears, the state of deep-dish pizza, and the secrets behind surviving the L in a single hour than you would in a lifetime of tours.

Looking ahead—don’t miss tomorrow’s kickoff to the city’s Art in the Garden extravaganza and get ready for a family-friendly Halloween parade at Washington Park this Saturday. Teeter on the edge of your seat, stay curious, and tune in next time for more wild discoveries and offbeat adventures around Chicago.

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/3V0gjPt

For more on Oly check out https://www.instagram.com/olybennet/

This content was created in partnership and with the help of Artificial Intelligence AI