Welcome, listeners, to Things to Do in Chicago, coming at you from the Windy City this Sunday, November 9th, 2025! Oly Bennet here, your globe-trotting champion of quirky fun, and if you’re craving more action than a Wrigley Field extra-innings thriller, you’ve tuned in to the right spot.

Let’s set the scene: It’s a crisp, classic November day, the Lake Michigan breeze is doing its thing, autumn leaves are swirling through Millennium Park, and the city’s electric as folks pack into neighborhoods from the South Loop to Wicker Park. The holidays are peeking around the corner, and Chicago is ready to turn up the volume on Sunday Funday.

Kicking off with today’s high-energy happenings—there’s something for every flavor of fun. First up: the Chicago Toy & Game Fair is in full swing at the Donald E. Stephens Convention Center, boasting a whirlwind of interactive exhibits, yo-yo championships, live toy battles, and even mascot sightings. If you want to catch Benny the Bull in the wild or vote on the Toy of the Year, this is your wonderland. Bonus points if you challenge a stranger to Giant Jenga—Oly’s official recommendation for making instant friends, or frenemies, depending on your skills.

If culture and the arts are calling your name, Dorothy Menker Theater is serving up chills and chuckles with their final showings of The Mel Brooks Musical: Young Frankenstein. For families, Brookfield Zoo is wrapping up its Tree Trim event, inviting you to channel your inner squirrel and help decorate the zoo for the holidays. Meanwhile, poetry lovers can dive into Earth & Echo: A Black Nature Poetry Gathering at Sand Ridge Nature Center, for a blend of words and the wild.

But hold onto your socks, there’s more: Columbia College Chicago’s Terranium Exhibit, The Conundrum of Coexistence, with stunning wildlife art, is still on display and free to attend, making a perfect pit stop for curious minds. And for a twist of history, check out the Halma board game event at Chicago Public Library—did you know Halma is German, not Chinese? Minds blown, trivia points earned.

Turning to city news and buzz, Queensyard has officially opened near River North, dazzling foodies with its British-American menu and sweeping river views—a hot new brunch destination in a city already obsessed with brunch. The CTA just announced enhanced train service for the holidays, so snag those ventra cards and leave gridlock to the taxis. For those wanting the inside scoop, Chicago’s newest immersive playground, EmotionAir by the Balloon Museum, is causing a stir in West Loop. Think epic balloon sculptures, interactive installations, and more Instagrammable moments than you can shake a selfie stick at.

Oly’s must-dos for today: Grab a slice at Pequod’s, warm up with a walk on the Lakefront Trail, or skate through Maggie Daley Park—those outdoor rinks are now open, and nothing says Chicago like trying to stay upright on ice as skyscrapers gleam overhead. If you’re in the mood for mischief, spot all 16 public art cows now scattered around the Loop—a citywide scavenger hunt that’s pure bovine brilliance.

Pro tip: For the real local vibe, never call it Willis Tower. It’s Sears Tower, full stop. Bonus Chicago cred if you work “dibs” into a conversation today—locals will know exactly what you mean.

On the horizon for tomorrow, Tuesday, be sure to catch Columbia College’s Veterans’ Day Celebration and the start of the Veterans Art Exhibition. Plus, the Christkindlmarket is prepping for its grand return—get ready for mugs of hot spiced wine and the original stuffed pretzel.

Don’t miss a beat—tune in tomorrow for more wild and wonderful ways to conquer Chicago like a true fun-seeker.

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, globe-trotters and thrill chasers, to Things to Do in Chicago with your eternally excited host, Oly Bennet! It’s Saturday, November 8th, 2025, and the Windy City is in rare form—crisp autumn air smelling like roasted chestnuts, a sky as blue as Lake Michigan, and a city pulse that’s practically daring you to skip the couch and dive into adventure.

This morning, people are out bundled in cozy layers, grabbing pumpkin lattes while skaters spin through Millennium Park and bold runners rack up miles along the lakefront. And the big city buzz? Nonstop. According to Chicago Magazine, the Black Harvest Film Festival is lighting up the Gene Siskel Film Center, showing off some of the brightest new Black filmmaking talent from all around, and it’s running all week for your movie-loving hearts.

If you’re the laugh-out-loud type, this weekend is a goldmine: The United Center is packed for Druski’s Coulda Fest Tour, a blend of comedy and music with guest stars—get ready for some surprise appearances and probably laugh until you look like you ran a marathon. Craving even more laughs? Get to the Comedy Bar Main Stage tonight for Dean Stanfield, an Austin-based comic and race car driver (seriously!), whose stories will have you snorting into your legendary deep-dish slice.

For families and future inventors, Siegel Hall is hosting Family Fun Day: Materials and Motion—a hands-on STEM day for kids ages 7 to 12. Expect science to look a lot like magic when things start rolling, floating, and bouncing across the room. That’s good energy for both tiny tinkerers and their caffeine-clutching parents.

Comedy connoisseurs can keep riding high with Sketchfest Chicago at the Home Comedy Theater, where the RENS (DC), Jackie & Allison, and hometown crew Big Freak will parade out a night of funky, character-fueled sketch comedy. Who said sketch was just for TV? In this city, it's a full-body workout for your funny bone.

For a cool, low-key evening, drift into the Epiphany Center for the Arts for Golden Hour—free, live music, drink specials, and the perfect excuse to debate which came first: the art or the vibe. Mingle in the transformed church-turned-gallery where every echo feels a little epic.

Before trekking out, a heads-up on city goings-on: According to the United Center’s latest updates, the Uber Zone for event drop-offs and pick-ups is now at Madison and Wood, streamlining your arrival for big shows. And speaking of arrivals—word on the street is a new ramen spot just opened in Logan Square, already earning raves for broths thicker than the plot of an indie film. Chicago never stops slurping, am I right?

If you’re hunting for classic sights and sneaky gems, don’t pass up an afternoon stroll through Lincoln Park’s fall gardens, the DIY vinyl hunt at Empty Bottle’s 33 and a third anniversary bash, or a browse through the bustling Holiday Craft Show in Frankfort if you fancy hobnobbing with crafters and finding early presents you’ll be tempted to keep for yourself.

Your local tip from Oly: When asking a local where to get the “best” anything—pizza, jazz, or even directions—prepare for a passionate, unsolicited Top Ten list and possibly a 20-minute story about someone’s grandma. That’s how you know you’re doing Chicago right.

Catch that festival spirit, keep an eye out for more pop-up jazz and secret speakeasy happenings, and get ready for tomorrow’s indoor food markets and the Eyrie Festival’s grand finale.

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, fabulous listeners, to Things to Do in Chicago! It’s Friday, November 7, 2025, and I’m your globe-hopping, high-fiving host, Ollie Bennet—ready to launch you into Chicago’s whirlwind of sights, sounds, and shenanigans. Let’s lace up those metaphorical sneakers, because this city never sits still!

First things first: Chicago’s serving up classic November flair—a crisp, invigorating breeze off the lake, perfect for layering up and showing off your best autumn style. Skies today are a cinematic mix of sun and clouds, so whether your plans are street parading or museum marathoning, the Windy City is primed for adventure. The city’s energy? Electric! The holiday sparkle begins to flicker in shop windows, and you can practically smell the hot pretzels on Michigan Avenue.

Now onto the action—what’s popping off today that you absolutely can’t miss? For the culture crusaders, the legendary Black Harvest Film Festival is animating the Gene Siskel Film Center with stories by Black filmmakers, diving deep into the richness of the Black experience. Expect everything from dazzling shorts to powerful documentaries, with special nods to Chicago’s own creative talent.

Music lovers, get ready! Jo Koy is storming the stage at United Center with his Just Being Koy Tour. Known for his sidesplitting stand-up and uncanny ability to turn family quirks into comedic gold, Jo Koy promises belly laughs by the bucketload tonight.

Swing over to Oak Park if your taste buds are tingling. There’s a free tasting event featuring Japan's No. 1 Dumpling popping up, so bring your appetite and your curiosity. Fans of jaw-dropping artistry can catch the ongoing Day of the Dead Quilts Workshop at the National Museum of Mexican Art—immerse yourself in color, texture, and tradition as local artists share the stories of the season.

Looking for giggles with a dash of the bizarre? Head to the Neo-Futurists’ The Infinite Wrench, a turbo-charged theater spectacle where they attempt to cram 30 mini-plays into 60 minutes. Think of it as speed dating for your attention span—no two nights are the same, and surprises are guaranteed.

Families, have no fear—fun runs rampant! The LEGO Group’s Holiday Lane at Water Tower Place is stacking up holiday joy, while kids can channel their inner artists at Fall Art Camp in Riverside. For movie buffs who love nostalgia with their popcorn, ChiTown Movies in Pilsen is spinning drive-in magic all weekend.

Let’s pivot to the latest Chicago buzz. The Old Town Pour House in Oak Brook has dropped a fresh Chef Selects menu, guaranteed to delight foodies. If you’re tackling the city by L—the Red Line’s just had a slick new update, which means smoother rides ahead for transit warriors. And, if you’re hunting for a new haunt to fill your belly, rumor has it there’s a ramen spot opening soon near Wrigleyville—keep your chopsticks at the ready.

If time’s tight and you want maximum Chicago in minimum moments, hit Millennium Park to admire the shifting autumn colors reflected in Cloud Gate. For a local favorite, stroll the Chicago Riverwalk, where street performers crank up the pulse and the iced lattes flow even as the leaves fall. Fancy feeling like a true Chicagoan? Order your hot dog “dragged through the garden”—translation: loaded with all the classic toppings, but never ketchup!

Here’s your Ollie Bennet fun fact: Chicago’s downtown is built on layers, literally—a street-level sandwich where you can walk above, below, or sometimes through history. There’s a secret network of tunnels and lower streets used for deliveries and, if you believe the legends, once for a few sneaky Prohibition-era getaways.

And before you dash off, a quick teaser: Tomorrow’s calendar is stacked with holiday markets, tree lightings, and perhaps an appearance by someone in a red suit with a beard—you know, for those already humming Jingle Bells. Join me again for more wild ideas, local legends, and off-the-wall 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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Welcome, listeners, to "Things to Do in Chicago" with Oly Bennet, globe-trotting fanatic for all things quirky, fun, and delightfully unexpected! It’s Thursday, November 6, 2025, and while the Windy City might have a nip in the air, the vibes are as vibrant as a deep dish pizza—steaming, layered, and absolutely irresistible.

Today the fall chill is rolling in, leaves are crunching underfoot, and the city feels like a movie set for every rom-com ever, just with more bean-shaped sculptures and less accidental coffee spills. Chicago bears a real energy boost right now as the last pre-holiday events stack up and people are squeezing in more outdoor adventures before winter wins the showdown.

Let’s jump straight into today’s lineup, and folks, it’s packed tighter than a CTA train at rush hour! Kicking off for music lovers, Hot Water Music is bringing their fiery punk rock to the Byline Bank Aragon Ballroom at 5 PM—get ready for some crowd-surfing and singalongs that’ll warm you up faster than a Lake Michigan polar plunge, as listed by Chicago Theater.

Comedy fans, file this under can’t-miss: tonight at The Chicago Theatre, Ralph Barbosa brings his “Bean Without a Cause Tour” to town. Prepare for a laughter marathon—doors open at 7 PM, so get those tickets ready and your cheeks primed for some serious smiling according to MSG.

Over at Navy Pier, the Chicago Children’s Museum is turning childhood nostalgia into an absolute joy-fest with “Take Care with Peanuts: The Exhibit.” Transport yourself into Charles M. Schulz’s world—test your piano skills with Schroeder, try Lucy’s advice booth, or join Snoopy on an epic adventure. It’s interactive, heartwarming, and perfect for families of all ages, running through January as announced by Navy Pier.

For those with a love of discovering the city itself, guided architecture tours at the Chicago Cultural Center are in full swing, offering glimpses into wild art installations and architectural quirks—there are still slots for today, highlighted by Chicago on the Cheap.

And if your idea of nightlife blends ice skating and stunning city views, head over to Maggie Daley Park for the outdoor skating ribbon, where experts and first-timers alike glide beneath the skyline lights. The ribbon is open, the cocoa is hot, and the selfies—let’s face it—are pure gold.

In local news worth chatting about over a loaded hot dog (yes, no ketchup debate today): look out for traffic delays around the Loop, thanks to set-up for the Christkindlmarket at Daley Plaza. It’s one of Chicago’s biggest holiday traditions, so even if you spot construction, think of it as a sneak peek at cheerful chaos to come, as reported by Daley Center. On the food front, rumor has it a new vegan bakery just opened in Wicker Park—look for the green awning and the line of hipsters trying to decide if croissants taste better with oat or almond milk.

Public transit remains your friend today: CTA updates say everything is running smoothly, so save money and skip the hunt for parking—unless you’re competing in your own private “Circling the Block Grand Prix.”

Must-do activities today? Embrace the season with a walk through Millennium Park—snap a photo at Cloud Gate, then duck inside the Art Institute to thaw out beside Monet’s haystacks. Or, if you like treasures that fly under the radar, stop by the International Museum of Surgical Science for exhibits that are both spooky and fascinating—imagine a haunted house for the brainy crowd.

Sporty tip from yours truly: if you’re feeling intrepid and want to channel peak Chicago energy, challenge a friend to the stairs at Swallow Cliff Woods out near Palos Park. Your legs will burn, the view is epic, and you’ll have an excuse to reward yourself with a multi-pound Italian beef later.

Fun fact to wow your friends: The Chicago River is the only river in the world that flows backward, thanks to an engineering flip-flop in 1900—proof that this city doesn’t just roll with the punches, it throws them right back.

Don’t close your calendar yet—tomorrow brings Druski’s outrageous “Coulda Fest” at the United Center, and for the culture vultures, the Chicago Architecture Biennial continues with new installations.

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, sports fans, and lovers of the wonderfully bizarre—this is "Things to Do in Chicago," with your intrepid host, Oly Bennet! Today is Sunday, November 2, 2025, and the Windy City is shaking off autumn’s chill with a classic blend of lakeside breezes and a cozy, golden glow from those soon-to-be-bare trees. Pack a scarf, but keep your sunglasses handy, because Chicagoans know how to make magic no matter the forecast.

The vibe across the city today? Vibrant, lively, and just a little bit nutty—as always. Marathons of art, music, and food are in full swing. The Hot Chocolate Run pumped up Grant Park early this morning with enough cocoa to launch a sugar-fueled stampede. For the film buffs, the Rooftop Cinema Club is throwing its Muffins & Mimosas bash, screening “How to Lose a Guy in 10 Days” complete with mimosas and lawn games, set against jaw-dropping city views. It’s Sunday Funday, Chicago style, where brunch meets big-screen romance.

Now, for listeners craving laughs, Roy Wood Jr. takes over the House of Blues tonight with his “Man of Many Fathers” Book Tour. Expect stand-up sharp enough to slice that deep-dish pizza you ate for breakfast, paired with storytelling only a Chicago crowd could inspire. Meanwhile, music fans can catch Pinkpantheress wrapping up her sold-out run at the Aragon Ballroom—a true feast for your eardrums before she inevitably jumps to stadium status.

Families, do NOT miss "EmotionAir: Art You Can Feel" at The Field Studios. Imagine nearly 20 giant, immersive balloon installations—think bouncy castle meets art museum. It’s like Willy Wonka and Cirque du Soleil had a baby right in the middle of Chicago, and it runs through April. Prefer your art classic and jaw-dropping? The Chicago Architecture Biennial’s new exhibit “SHIFT: Ecologies” at 840 N Michigan Avenue features more than thirty astounding installations exploring how cities and nature collide.

On the cultural front, November marks the start of “It’s Theatre Season”—thanks to the League of Chicago Theatres, it's buy-one-get-one-half-off at more than fifty live performances. Whether you fancy musicals or moody Victorian mysteries, you’re covered—and your wallet won’t weep.

Now for some local buzz sure to spice up your group chat. The city’s transit system is humming smoothly, with the Red Line rolling reliably, and new late-night bus routes giving night owls extra wings. For foodies, River North just welcomed “Bacall’s,” a wild new spot where diners huddle around Finnish-style fire pits, roasting their own sausages and telling Chicago ghost stories. It’s already the place where “everybody knows your name”—or at least pretends they do.

If you only do three things today, here are my picks:
Brave the views at the Skydeck Ledge in Willis Tower—nothing like dangling over the city to remind you you’re alive. Drop by Pilsen for murals so spectacular your phone may overheat from all the photos. And cap it off at the Logan Square Farmers Market, where you can score rooftop honey, pear cider, and—if you’re lucky—a small-batch pierogi that could bring a tear to your eye.

Chicago fun fact of the day: The deep-dish pizza was invented in 1943 at Pizzeria Uno, but many locals secretly swear allegiance to the thin, crispy “tavern-style” square-cut pie. Order both—no one will judge. In fact, you’ll fit right in.

Big heads up for tomorrow! The city gears up for the opening night of the Joffrey Ballet’s “Matters of the Heart” at the Harris Theater and, for all you book lovers, the release of a new “American Prophets” exhibit at the American Writers Museum dives into creativity, culture, and spirituality—in true Chicago fashion.

Don’t miss a beat—tune in tomorrow as we dig into the quirky, the classy, and the utterly unexpected. 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 to Things to Do in Chicago, Oly Bennet reporting for action on this spirited Saturday, November 1st, 2025! Grab your wind-cheaters and a hearty coffee because today, the city is greeting us with brisk autumn energy—chilly breezes off Lake Michigan, a patchwork of golden leaves, and a vibe that's as electric as a Wrigleyville crowd after a ninth-inning home run.

If you love sneakers more than you love putting your left sock on first, today’s main event is Sneaker Con Chicago at the Schaumburg Convention Center. It’s not just a swap meet—it’s the “Greatest Sneaker Show on Earth,” with hundreds of vendors, sneaker restoration, live games, and mind-blowing rare grails on display. Swoosh by, flex your freshest kicks, and maybe spot a celebrity guest or become a viral video star for a day, according to the event site Sneaker Con Chicago.

Craving high drama and a bit less leather? The Lyric Opera of Chicago unleashes opera’s most thrilling double feature, Cavalleria rusticana & Pagliacci, starting today. Word on the street from the Lyric Opera is that this is the sort of performance that makes you clutch imaginary pearls and hum Italian arias all the way home.

If you fancy a throwback to legendary show tunes, the James M. Nederlander Theatre is staging The Sound of Music, that perennial goosebumper filled with “Edelweiss,” “Do-Re-Mi,” and enough twirling hills to make you dizzy with joy. It’s perfect for the whole family and showing only until tomorrow, so don’t miss your shot at a little musical magic, notes Chicago-Theater.com.

For a sprinkle of mystery and enchantment in the great outdoors, brave the Harry Potter: A Forbidden Forest Experience, which transforms the woods outside Chicago into a spellbinding, interactive adventure. Wave a wand, dodge a Dementor, and geek out with friends and family.

Shifting into citywide buzz: Chicago’s food scene is heating up with the grand opening of Prairie Fire 2.0, a modern Midwestern bistro in West Loop drawing crowds with elevated comfort food and legendary apple pie. Meanwhile, the CTA reminds all Red Line riders to plan for reroutes this evening due to ongoing construction. For those exploring after dark, hop on a Divvy bike and whiz lakefront-style—local tip, your first ride under 30 minutes is often free!

Every Chicago adventurer needs a little secret sauce. Here’s a quirky one: the city’s official font for street signs is called Chicago Sans. That’s right—the same town that gave the world deep-dish pizza also customized its own way to say "STOP."

Looking ahead, tomorrow’s calendar sparkles with the kick-off parade for Chicago’s International Comedy Festival—expect improv greatness, sidewalk stand-up, and surprise guest appearances all over River North. If you're more of a foodie than a jokester, the ever-popular Logan Square Farmers Market is set for a special fall harvest edition, brimming with cider donuts and live tunes.

Pack your sneakers, opera glasses, and sense of adventure—tomorrow’s line-up promises more surprises. 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 with Oly Bennet, your globe-trotting, sports-obsessed guide to the world’s quirkiest adventures! It’s Friday, October 31st, and Chicago is feeling deliciously electric—Halloween’s got the Windy City in full-on costume mode, with crisp fall air, pumpkin-scented breezes, and that thrilling tingle that only comes when everyone, everywhere, is ready to party!

If you’re wondering what’s cooking in the city today, it’s a cauldron of culture, fun, and chills. Let’s start with The Other Art Fair at Artifact Events in Ravenswood. Today only, this art fest transforms into an art-powered Halloween bash, with DJs, a wild butterfly taxidermy workshop led by The Insect Asylum, tintype portraits, and a full-on costume contest. More than 115 independent artists are strutting their stuff—a top pick for anyone looking to get weird and creative today, according to Secret Chicago.

If you’re chasing that classic spooky spirit, the Haunted Halsted Halloween Parade is marching across Northalsted tonight. Think giant puppets, eye-melting costumes, stilt walkers, and enough glitter to cover Grant Park twice. This is not just a parade, it’s an all-ages showstopper with a prize-packed costume contest. Looking for more rising heart rates? The Chapel of the Undead Costume Event at Sound Bar is Chicago’s late-night answer to “What if a vampire nightclub met a DJ rave?”—pure, unfiltered nighttime madness.

For families, there’s no shortage of candy-crazed action. Brookfield Zoo is running “BOO! At the Zoo”—trick-or-treating, spooky inflatables, magicians, and haunted treats from morning to evening. West Town’s Jack’s Pumpkin Pop-Up is a pumpkin-palooza with corn mazes, axe throwing, and enough pumpkins to build a Cubist sculpture. Want something more community-powered? Head to El Paseo Boricua for the Haunted Paseo, a free, family-friendly fiesta with food, games, and a community haunted house. There’s even a Trunk or Treat event at Paschen Park, where your best costume might land you extra sweets.

Sometimes, Chicago just keeps the fun rolling with concert and nightlife choices that will launch you into November wide awake. The House of Blues is conjuring House of Boos, a jam-packed music bonanza, while Chicago Eagle hosts BEEFWITCH, a legendary occult underwear party making its first windy city appearance tonight, promising goth pop, dance rituals, and a midnight floor show.

On the city beat, in case you missed it, the Red Line “L” trains are running extra service for tonight’s festivities, with late-night trains and security teams to help costumed commuters bounce from party to parade and back. Restaurant hounds, listen up: Avli River North recently unveiled a spooktacular Greek-inspired Halloween menu, and JoJo’s Shake Bar has transformed into a wild pumpkin patch, serving outrageous milkshakes alongside bonkers fall treats.

My must-dos for the restless and bold? If you’ve never Instagrammed from The Bean at midnight in costume, tonight’s the night—with a rumored flash mob dance-off in Millennium Park after the parade. Want a local gem? The WNDR Museum, an ever-evolving interactive art wonderland, is running a special “Glow Night” experience—bring a friend and see who can dance the wildest on the LED Light Floor.

Pro tip: In Chicago, the best bathrooms during parade nights are at the Chicago Cultural Center—clean, roomy, and open late. And did you know the city’s Halloween parade tradition dates back to 1920, when revelers marched down State Street dressed as… radishes? True story, and a reminder: Chicago weird is Chicago wonderful.

Don’t dash off yet—tomorrow’s bringing the Little Village Arts Festival, Day of the Dead magic at the National Museum of Mexican Art, and fresh harvest fun at neighborhood farmers markets. I’ll be back with more wild picks, untold stories, and epic Chicago quirks.

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, wild wanderers and curious competitors, to Things to Do in Chicago with your globetrotting, game-obsessed guide, Oly Bennet! It’s Thursday, October 30th, 2025, and Chicago is absolutely buzzing — think deep-dish oven heat with a side of electric excitement as Halloween creeps ever closer. The weather’s got us in classic fall mode: jackets at the ready, scarves out in force, pumpkin spice in the air, and probably a toddler in a dinosaur costume waving at a Dalmatian-dressed dachshund somewhere on Michigan Avenue.

Chicago’s current vibe is a glorious mashup of haunted hilarity and serious style. According to Mommy Poppins, trick-or-treating is officially on today, and the whole city is candy-fueled and sugar-hyped. Not to be outdone, Dia de Los Muertos festivities are lighting up neighborhoods like Wrigleyville and Marquette Park with vibrant altars and dance performances—colorful skulls and even livelier spirits.

Let me hit you with today’s top events, guaranteed to fit every interest from headbanging to hand-holding:

Playboi Carti’s Antagonist Tour explodes into the United Center tonight at 7 pm, with Ken Carson, Destroy Lonely, and Homixide Gang joining the chaos. If your ideal cardio is pogoing in a sea of hypebeasts, this show is your jam.

Culture seekers, the Chicago Writers' Bloc Fall Festival lands at City Lit Theater, starring a fresh crop of new plays and musicals by local masterminds—expect drama, laughs, and maybe a flying pie or two just for that classic twist, as reported by Travel and Tour World.

Art lovers, feast your eyes at the Norris University Center, where “Street: Photographs by Ann Kogen” offers a black-and-white time machine into the city’s most candid moments. From Chicago sidewalks to Cairo’s chaos, Ann Kogen’s snaps capture humanity’s quirks in all their glory.

For the family crew, the big Halloween parade on Halsted Street is your costume contest, creative chaos, and candy extravaganza all rolled into one. Word is, even pets in tutus are highly encouraged—no judgment, just cheers.

Night owls, the House of Blues has you covered with live blues and the Chicago Comedy Club tonight. Drop by for toe-tapping tunes and, who knows, an impromptu dance-off as the music seeps into your soul.

How about what’s new off the field? A few fresh tidbits got locals talking: The Chicago Architecture Biennial is dazzling with massive art installations tucked between beloved skyscrapers — the perfect reason for a spontaneous selfie marathon. Meanwhile, Green City Market is still serving up fresh local bites, so come hungry and leave with arms full of apples, pumpkins, and the best damn donuts this side of Lake Michigan.

Heads up on city logistics: With all the action downtown and Halloween crowds, public transit is your friend. The CTA’s ramping up service, especially along the Red and Blue lines, so ditch the car and ride the rails like a true Chicagoan.

Top must-do activities: Snap an iconic selfie at “The Bean” before the crowds descend, then skip the usual river cruise for a stroll through Jack’s Pumpkin Pop-Up—it’s a pumpkin patch, corn maze, and full-throttle autumn fairground smack in Goose Island. Or duck beneath the ghostly glow of ghost tours winding through River North’s hidden speakeasy bars. Feeling extra? Hunt for quirky murals in Pilsen—your Instagram will thank you.

Local tip for maximum cred: If someone invites you for an Italian beef, say yes, then order it “dipped”—because the sandwich is supposed to soak up so much juicy gravy you need two hands and a whole stack of napkins. Trust Oly: get messy and earn your Chicago stripes.

Coming up tomorrow, get ready for CreepAid 25 at the Copernicus Center and the city's spookiest dance parties lighting up the night. Spoiler: costumes are strongly encouraged, and glitter is practically mandatory.

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—your daily adventure download with Oly Bennet, where the only thing more surprising than a Chicago wind is the city’s wild event calendar! Today is Sunday, October 26, 2025, and let me tell you, the Windy City is absolutely buzzing. Right now, we’re waking up to crisp autumn air with a high near 59 degrees—perfect for cozy layers and city exploration. Halloween energy is creeping in, every corner smells like pumpkin spice, and the lakefront is practically shimmering with anticipation.

Whether you’re a sports fanatic, music lover, family wrangler, or nocturnal party prowler, Chicago’s got you covered. Here’s the Oly Bennet field report for today’s top happenings.

Tonight, get your pulse thumping at the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena. Chicago rapper G Herbo is rallying an all-star crew—21 Savage, Polo G, Meek Mill, and more—starting at 7 PM. Hot tip for the fashionistas: leave your bags at home, because Wintrust is going full “no bags, no purses, not even clear ones.” Pro tip: use their outdoor lockers on Cermak and Indiana early—they’re first come, first served.

For partygoers chasing summer-in-the-Caribbean vibes, Reggae Sunday is cranking things up at Bassline from 10 PM. This bash—dubbed “The #1 Caribbean Party in the City”—will drench you in reggae, dancehall, and Afrobeat rhythms from top international DJs and live dancers. Expect a packed floor, electric cocktails, and Chicago’s wariest dancers dropping moves that would make a flamingo blush.

Family folks, the city’s got you. Daylight is prime time for Fall Family Fun at Oak Park Public Library with their Costume Parade and resource fair, perfect for little monsters still high on Saturday’s sugar haul. Plus, if you’re close to Gallagher Way, their legendary Pumpkin Party runs all afternoon—the only thing missing is a pumpkin spice latte for your jack-o’-lantern.

Culture vultures, this afternoon don’t miss “Short Summer” at AMC Newcity 14—a short film festival bringing international flair for the artsy crowd. And, puck-heads, tonight’s the night: the Chicago Blackhawks take on the LA Kings at United Center at 6 PM. Gates open at 4:30, so get there early, say hi to an overly-caffeinated Oly Bennet lookalike, and find your seat for some classic midwest ice chaos.

On the local scoop, Chicago’s buzzing about a round of new restaurants opening up in the West Loop—expect fiery Korean BBQ and Argentinian pastries lighting up Randolph Street. If you’re hopping around town, remember: the CTA Blue Line is your friend for United Center or West Side events, but watch for weekend work on the Red Line with some delays closer to Chinatown.

Not sure how to squeeze out every ounce of Chicago charm today? Hit Millennium Park—the selfie with The Bean is essential, but here’s Oly’s pro-move: explore the under-visited Lurie Garden just beyond, a quiet green hideout with skyline views and plenty of chill Sunday energy. For a quirky twist, check if you can spot the Picasso statue on Daley Plaza—it’s the only Picasso you can climb on. That’s right, listeners, in Chicago you can literally clamber onto a priceless piece of art.

Before we wrap, a fun Windy City fact: Chicago’s nickname doesn’t come from the weather, but 19th-century politicos who were “full of hot air.” See, even the city’s gossip is legendary.

Don’t hang up your adventure boots yet—tomorrow’s teasing legendary Halloween events, rooftop parties, and the big Christkindlmarket setup at Daley Plaza. You’ll want to tune in for Oly’s picks for costumes, candy, and the weirdest haunted happenings in 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.

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Welcome, energetic explorers, to Things to Do in Chicago! It’s Saturday, October 25, 2025, and I’m Oly Bennet, your globe-trotting sports nut turned event adventurer, live from the city where the lakefront breeze could host its own kite festival and deep dish pizza is basically an Olympic event.

Chicago this morning is serving up what locals call “sweater weather”—a cool, crisp fall day that’ll have you clutching your coffee and snapping way too many pics of those golden leaves. Everyone’s buzzing, thanks to Halloween on the horizon and an avalanche of happenings crashing into your weekend.

First up, for you comedy junkies and improv lovers, Ben Schwartz and Friends are taking over The Chicago Theatre tonight at 8 p.m. Expect wild scenes, famous faces, and enough laughs to pull a muscle you didn’t know you had, straight outta the multiverse—seriously, this will fill up fast, so get there early, and maybe practice your improv prompt in line just in case you join the action.

If live music vibes are more your jam, head to the legendary Old Town School of Folk Music. There’s a double-header at 8 p.m. featuring the rootsy sounds of Tobacco City—a toe-tappin’ journey through Americana sure to leave your inner cowboy high-fiving your inner jazz cat. And if you’re feeling artsy, just a few blocks over Epiphany Center for the Arts is open for exploration with golden hour drinks, a pre-show buzz, and that gallery-rambling atmosphere that makes you feel instantly cooler.

Movie buffs, the Rooftop Cinema Club is screening Hocus Pocus tonight. Think classic witches, city skyline, popcorn, and all the cozy fall feels under the stars—bonus points if you show up in costume, because honestly, who isn’t ready to let their inner Sanderson sister run wild before Halloween?

Families and creative souls, check out BUILD Chicago with free drop-in art studios and science experiments through the afternoon at 5100 W Harrison Street—no fancy tickets or experience required, just curiosity and maybe a paint shirt you don’t mind covering in accidental masterpieces.

Photography fiends don’t miss the “Street” exhibition by Ann Kogen, open all day at Dittmar Gallery at Northwestern’s Norris Center. Take a time machine back to the 1980s through her stunning black-and-white street photos—think big hair, bold moments, and those raw slices of city life that never go out of style.

Splashing into news: According to local transit updates, the CTA is running extra trains tonight for safe shenanigans, and there’s buzz about a new ramen spot opening in Wicker Park—because nothing says autumn like hot noodles and bragging rights for trying the city’s swankiest slurp.

For today’s must-do list, make the most of Millennium Park's evolving fall color show, pop into the Chicago Cultural Center (always free and always fascinating), and sneak in a walk along the Riverwalk before the winter chill muscles in. If you’re craving a quirky adventure, jump on the L and pick a random stop—some of Chicago’s best treasures are hiding in the neighborhoods.

Oly’s local tip? If you want to feel like a true Chicagoan, layer up, leave the umbrella at home, and don’t be shy about asking your server for their favorite dish—they take local pride seriously, and you might discover something that makes your taste buds do the wave.

Tomorrow is packed with even more festivities—keep an eye out for gallery walks, pop-up brunches, and last-minute Halloween costume contests. I dare you to tune in again and see what wild, wonderful antics this city has in store.

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