Welcome, my globe-trotting, thrill-seeking listeners to “Things to Do in Chicago” on this fine Sunday, October 5, 2025. This is Oly Bennet—your favorite source for discovering the wild, wacky, and wonderful across the Windy City. This morning, Chicago’s got that early fall magic in the air: brisk, lively, and absolutely perfect for a day of adventure. The city’s streets are buzzing with bundled-up crowds, and even the squirrels are wearing their autumn best.

Today, the city is all about *variety*, and oh boy, does Chicago deliver! If you’re craving rare finds and vintage treasures, Modern Vintage Chicago turns Ravenswood Event Center into a one-day paradise for collectors and fashionistas—bring an eagle eye and channel your inner treasure hunter. Over in Hyde Park, families and fitness fans can lace up for the RBC Race for the Kids at Comer Children’s Hospital, adding a dash of heart and hustle to the morning. For your culture fix, the legendary Chicago Architecture Biennial keeps the city marveling with installations and urban spectacles, while the Destinos Latino Theater Fest energizes the National Museum of Mexican Art with vibrant performances that can make even the most stoic Midwesterners bust a move. If you’re the type who needs a snack and a stroll, don’t skip the Glenwood Sunday Market or the iconic Maxwell Street Market, where produce, pastries, and pop-up surprises fuel your day.

But wait, what’s that sound echoing from the Chicago Theatre? That’s none other than “John Candy I Like Me: An Evening with Ryan Reynolds & Friends!” Get ready for side-splitting comedy and celebrity antics, right under the marquee at 175 N State Street. If you’re more into quirky local traditions, look out for Jack’s Pumpkin Pop-Up on Goose Island, where corn mazes meet Chicago-sized seasonal energy—this is not your grandma’s pumpkin patch! Night owls, the ART on THE MART digital projections along the Riverwalk will light up your evening with mesmerizing creativity and some serious photo ops.

Chicago’s local news? The grand opening of Auntie Anne's + Cinnabon Co-Brand Flagship downtown means cinnamon-scented air and pretzel lovers unite. Transit riders, good news: extra express shuttles are navigating to and from the Burnham Wildlife Corridor for tonight’s Mid-Autumn Festival finale—mooncakes, music, and a lantern procession set the lakefront aglow. If you’re driving, keep an eye out for the city’s expanded street cleaning schedule and grab that spot early, unless you’re into post-event parking scavenger hunts (hey, some people call it sport!).

As far as must-dos, don’t miss ART on THE MART for an evening stroll—it’s like watching Picasso get wild with a laser pointer. The Lincoln Park Blues and Gangster Tour gives you a walking, talking history lesson straight from Chicago’s nefarious past. And for a local secret: If you’re aiming for truly legendary deep dish, take a detour to Pequod’s in Lincoln Park. Their caramelized crust is basically Chicago pizza in full beast mode—trust Oly, this is the taste bud trophy you want.

Want to fit in like a native? The first Sunday of every month means discounted museum entry for Illinois residents, so bring your state ID and map out a mini-culture marathon. Remember, in Chicago, jaywalking is an art form and umbrella defense is crucial—watch those wind gusts, folks!

Tomorrow, keep your eyes peeled for even more festivals, the start of Open House Chicago, and fall’s biggest food events. Whether you’re up for architecture tours, river rambles, or late-night laughs, 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.

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Hello there, globe-trotters Welcome to "Things to Do in Chicago" It's October 4, 2025, and we're diving into all the excitement this city has to offer. The weather in Chicago is crisp and perfect for exploring, making it a great day to get out and enjoy some of the fantastic events happening around town.

Today, you can start your day with the Oak Brook Artisan Market at Oakbrook Center or head to the Aki Matsuri at Christ Church of Chicago for a taste of Japanese culture. If you're looking for something more adventurous, don't miss "BOO at the Zoo" at Brookfield Zoo, a fun event for the whole family. For music lovers, there's "Mixtapes + Mimosas" at Fora, offering live music every Saturday.

On the nightlife front, the Taste of Northhalsted is a must-visit for food and entertainment. In local news, the recently opened co-brand flagship of Auntie Anne's and Cinnabon on Michigan Avenue is a perfect spot for a sweet treat. Remember, navigating Chicago is easy with the "L" train, so grab a Ventra card and explore like a local!

A fun fact: did you know that Chicago hosts the Chicago Architecture Biennial, a global design event that runs through February? It's a great time to explore the city's architectural highlights.

Tomorrow, be sure to check out some of the ongoing events like the Destinos Latino Theater Fest and the World Music Festival Chicago for a dose of cultural richness.

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 QuietPlease dot Ai.

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Welcome, listeners, to Things to Do in Chicago with your resident globe-trotting, sports-loving, deep-dish devourer, Oly Bennet! It's Friday, October 3, 2025, and Chicago’s rolling into October with a jolt of high-energy goodness—think pumpkin spice but with more attitude. The air is crisp, the leaves are flirting with full-on gold, and the city’s electric with a lineup of events wild enough to impress even a jaded marathon runner.

Today’s weather? Brisk but brilliant—perfect for grabbing a sweater and stomping out into the action, whether your vibe is art, music, or chasing down the city’s quirkiest fun with friends and family.

Let’s talk about what’s popping today. First up, wine lovers, it’s your time to shine! The Lincoln Park Wine Fest is uncorking bottles and pouring tastes at Jonquil Park tonight starting at 5pm—expect top-drawer wines, food pairings, and a little sommelier wisdom sprinkled in, all for a good cause.

If you’re into art (and who isn’t, after seeing Chicago’s skyline?), the West Town Art Walk is on tonight from 5 to 8pm along Chicago Avenue. This isn’t just an art stroll—it’s a full-on creative bash with over 40 neighborhood businesses transforming into art galleries, performance spaces, and live music venues. It’s like a pub crawl but with paintings, percussion, and probably a stray ukulele or two.

Music junkies, the World Music Festival Chicago is in full swing, filling venues across the city with sounds from every continent. It’s free, it’s global, and you could literally go from Afrobeat to Andean pipes without leaving town. Up for a concert? Pool Kids and Truth Club hit Lincoln Hall’s stage tonight, and for a dose of classical flair, the Rembrandt Chamber Musicians are tackling Beethoven at 7pm—it’s highbrow with a side of toe-tapping.

Got little monsters? Check out the Rooftop Cinema Club in Fulton Market screening The Addams Family at 5pm—a ghoulishly good time for families. Or, for those after a retro groove, Chicago’s Southland is hosting Disco Circus at Gaelic Park, proving once and for all that bell-bottoms truly never die.

As night falls, Taylor Swift fans get spoiled with a “Life of a Showgirl” album bash at Pippin’s Tavern and another late-night party atop the Rooftop Cinema Club. Meanwhile, theater buffs, don’t miss The Infinite Wrench at Neo-Futurist Theater—a mad dash of 30 mini-plays squeezed into an hour. Pure creative adrenaline.

In today’s local news, foodies and carb connoisseurs can rejoice—today’s the grand opening of the Auntie Anne’s and Cinnabon co-branded flagship on Michigan Ave. That’s right: the dream team of pretzels and buns has hit the Magnificent Mile, so prep your taste buds.

Transit-wise, word on the street is CTA Red Line trains are running without major delays today—miracles do happen. For public art fans, the city is rolling out more interactive murals in Logan Square, so bring your camera and snap some new profile pics.

Must-do activities? Stroll Millennium Park’s gardens, check out the immersive digital exhibits at WNDR Museum, or duck into Garfield Park Conservatory for a splash of tropical warmth. For a quieter, hidden gem, try the art-and-toy mashup at Rotofugi—guaranteed to delight your inner kid (or very real kid).

Want to blend in like a local? Skip the deep-dish queues and duck into a tavern for a Chicago handshake—a shot of malört and a cheap beer. It’s an... acquired taste, but hey, you only live once.

Looking ahead to tomorrow, there’s the Lincoln Square Ravenswood Apple Fest, BOO at the Zoo at Brookfield, and the South Side Science Festival—all ripe for adventure. Tune in for more wild and weird happenings. Until then, keep exploring, keep laughing, and keep Chicago weird.

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, adventurous listeners, to Things to Do in Chicago, with your guide Oly Bennet—broadcasting live on this glorious Thursday, October 2, 2025. Today’s city vibes? Absolutely electric! Chicago’s waking up to balmy autumn temps bouncing from the upper 60s this morning to a toasty 80 by later today. Warm air means festival shirts, not flannel—so lose the parka, grab your sunglasses, and let’s dive into the day.

If you’re ready to squeeze every drop of joy out of a Chicago Thursday, I’ve got the quirkiest, coolest happenings on tap. First up, for those with taste buds that crave adventure, Port Wine Fest is pouring more fun than your uncle at Thanksgiving. From 5 to 8 p.m. at The Walden on West Walnut, over forty Portuguese wine producers uncork more than a hundred wines, including sparkling and legendary Ports—add in impossibly delicious bites and you’ve got an eat-and-sip extravaganza that doubles as a fundraiser for the Greater Chicago Food Depository. Swirl, sniff, and schmooze; tonight, your wine passport gets stamped Portuguese.

Next, music fans, warm up those air guitars—the Chicago Theatre is set to explode tonight when Queens of the Stone Age rock the house, joined by none other than Paris Jackson. The Catacombs Tour hits the historic State Street stage—doors open early, digital tickets ready, and if you’ve never been inside this legendary temple of tunes, tonight’s your chance for a legendary night out.

For families or anyone itching for a classic Midwest fall day, the Fall Festival at Sonny Acres Farm in West Chicago is pure pumpkin-powered bliss. From hayrides and mini roller coasters to roasted corn, taffy apples, and haunted barns that’ll have even the bravest adults squealing louder than the kids, this fest is open every day through October—a cornucopia of smile-inducing fun.

Cultural buffs, you’ll want to pencil in World Music Wednesdays at Old Town School of Folk Music—which continues as part of Chicago’s World Music Festival, serving global rhythms and dance with a local twist. Trust me, your Spotify playlist will never recover.

In today’s local headlines, the city’s showing off its global flavor with new restaurant alerts—word on Randolph Street is a brand-new Korean BBQ joint is firing up grills for both carnivores and veggie-lovers. Transit-wise, no major delays reported, but keep in mind some late-night work on the Red and Blue lines as part of CTA’s autumn upgrades.

Can’t-miss-moments for the day? Stroll Millennium Park, selfie in front of the Bean (bonus points for goofy poses), and, if you’re a thrill seeker, detour to the 360 CHICAGO observation deck for edge-of-your-seat views that’ll make your friends think you’ve scaled the Willis Tower with Spiderman agility. Feeling extra bold? The hidden gem of Garden of the Phoenix in Jackson Park is an oasis of Zen with autumn leaves twirling in technicolor.

Local tip: Hungry but hate waiting in line? Savvy Chicagoans use mobile order apps for deep-dish at Lou Malnati’s or grab snack-sized Italian beefs at iconic stands—always go hot and sweet with your giardiniera, trust me!

Before you dash, get your calendars ready—Open House Chicago returns October 18-19 with rare access to secret rooftops, hidden vaults, and the stories behind the city’s boldest buildings. And rumor has it, tomorrow's lineup includes a moonlit river boat party plus the return of Chicago's secret pop-up ping pong bar. Curious? Tune in tomorrow for the latest scoop.

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-trotting thrill-seekers and Chicago daydreamers, to Things to do in Chicago with your guide Oly Bennet! Today’s date is Sunday, September 28, 2025, and the city’s got that crisp fall energy buzzing through the air. Sweater weather is in full swing—expect sunshine, perfect jacket temps, and golden leaves swirling down Michigan Avenue. Outside, Chicagoans are already fueling up with pumpkin lattes and plotting their festival attack plans, because this city never naps on a Sunday.

What’s the city vibe today? Absolutely electric. We’ve got a smorgasbord of happenings: art lovers, music buffs, families, vintage fans—you’re all covered. Let’s serve up a rapid-fire rundown of some standout events happening right now.

For the artsy crowd, you can’t miss the second day of the Randolph Street Market Festival. This West Loop favorite is a treasure hunter's heaven: vintage finds, vinyl, crafty makers, typewriter poets mingling with food trucks, and a live music lineup that’s basically a Chicago road trip for your ears. Highlights today include the Tony Morrison Jazz Quintet, Joe Wortell & the Natural Good Country Western Band (bring your cowboy boots, y’all), and rockabilly beats by Al Simon & the Saturn Kings. It all runs through late afternoon—bring cash and comfy shoes, and prepare to adopt a flamingo lamp or three.

Fancy some musical highbrow? Over at Epiphany Center for the Arts, at 2 pm, the internationally acclaimed pianist and composer Philip Daniel weaves together classical and cinematic soundscapes in an intimate concert—the man’s basically the soundtrack to your autumn daydreams. Stick around for 100% Bachata Sunday at 6 pm, where the dance floor welcomes everyone to sashay and sway through Chicago’s juiciest Latin grooves. It’s their first-ever Bachata night at Epiphany, so bring your best spins!

Bringing the family? The Lincoln Park Zoo Fall Fest has you covered, with free admission, pumpkin patches, hay mazes, and sweet treats—yes, toddlers on sugar highs are a legitimate sport at this event. It runs every Friday, Saturday, and Sunday through October, and it’s a staple if you want a dash of Halloween without the mayhem.

For the sustainability-minded, the Sustainability Market is in full swing, offering eco-friendly finds, swap shops, and local green initiatives—a gentle reminder that saving the planet can be stylish, and Chicago is always on-trend.

In cultural news, the CheckOut music and arts venue just completed its grand opening celebration—it’s a converted 7-Eleven now pouring adult slushies and fueling affordable culture all season. The city is abuzz over this quirky new hangout spot.

Transit tip: CTA’s Red Line maintenance wrapped early this morning, so trains are running smoothly—no grumpy morning commuters today, just high-fives for transportation miracles. And if you’re eyeing brunch, two new restaurants just flung their doors wide in Wicker Park—a French-Vietnamese fusion bistro and a Mediterranean-Japanese hybrid. Chicago is officially a passport with a skyline.

Classic must-dos: catch the shimmering lake views from the Chicago Riverwalk, grab a selfie with The Bean before the out-of-towners mob it, and if you haven’t swung by a speakeasy yet, make tonight the night to tuck behind a bookshelf for cocktails and jazz.

Local tip from Oly: If you’re gunning for Chicago-style hot dogs, remember—no ketchup, unless you want a stern talking-to and possibly a side-eye from a lifelong Sox fan. Seriously, the city council might write this into law.

Hot tease for tomorrow: Don’t miss Alice Sara Ott’s rare back-to-back performances of Ravel’s piano concertos, plus get your bid on at the Village Chicago’s “Many Voices, One Song” gala with Broadway hits blaring and prize raffles galore.

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!” It’s Saturday, September 27, 2025, and as Oly Bennet, your witty wanderer of wild sporting feats and funky festivities, I’m here to launch you into a day that’s pure Chicago—quirks, crowds, crispy fall air, and an endless parade of epic stuff to do!

Chicago’s waking up to classic autumn energy. The breeze is cool, Lake Michigan is flirting with morning mist, and the city’s mood is crisp optimism colliding with serious weekend ambition. There’s a cheeky hint of Oktoberfest in the air, plus wild food smells wafting from city streets, and locals bundled up in their finest fall layers are out and about, already plotting their adventures.

Today’s events are a kaleidoscope of fun, so buckle up! First up, gather the squad and hit the **Randolph Street Market Festival** in the West Loop. Expect vintage treasures, indie fashions, epic people-watching, and live bands from blues to salsa. Bargain hunters and disco dancers unite—plus, the food lineup is a rollercoaster from Caribbean jerk chicken to legendary lobster rolls and donut-style beignets that might ruin your diet and your dignity. Take the kids: it’s free for under 12, and DJ Tiggs is sure to keep the outside stage vibing!

Craving culture? Head to Eugene Field Park for the free **Musika SamaSama Filipino Festival**—the only Filipino cultural bash in Chicago today! It’s Filipino food, artisan crafts, and fusion folk bands galore. If you fancy a side of karaoke with your Lumpia, this joyous gathering is your ticket to a tasty heritage trip.

For the foodies with massive appetites, the **Chicago Gourmet Food Festival** is the summit of culinary cool. It’s happening on the Harris Theater Rooftop from 2 till 10, hosted by culinary rockstars Stephanie Izard and Karen Akunowicz. With over 100 chefs serving up bites and boozy wonders, this is a legendary snacking ground—leave your calorie counter at home!

Families can get their stomp on at the **Rosetoberfest 5K Run/Walk & Fest** over in the Parkway Bank Park. Think Oktoberfest meets sneakers, plus face painting, live music, and snacks. For something softer, flutter over to the Peggy Notebaert Nature Museum for **Butterfly Haven Yoga** at 8:30 AM—stretch, breathe, and witness a first flight butterfly release that’ll melt even the toughest Chicagoan.

Night owls, not forgotten! As dusk falls, hit the **Rooftop Cinema Club** at Fulton Market to catch “Twilight” under the stars—nothing says mysterious cityscape like vampire romance with skyline views. Throw in the city’s legendary improv or a classic jazz dive, and you’re living your own Chicago story.

On the city news front, insiders are buzzing about the soft opening of a new ramen hotspot in Lincoln Park packing pork belly and egg like a flavor supergroup. The CTA trains are running smoothly this week—no reroutes, so you’re golden for cross-town adventures. Plus, local breweries are launching new batches in time for autumn so you might stumble on fresh pumpkin ale wherever you roam.

Here’s a local tip: If you want to dodge the slow tourist shuffle and move like a true Chicagoan, hop on a Divvy bike. City’s flat as a pancake, and autumn is prime pedaling weather. And fun fact—Chicago’s got more movable bridges than any city on Earth, so if you get stuck downtown, you might just see a riverfront bridge lift, which doubles as a real-life transformer show!

Looking ahead, tomorrow’s teasing a South Chicago Dance Theatre performance and the second round of Randolph Street Market magic. Plus, food festivals and concerts are waiting just around the bend. So keep your boots laced, your belly ready, and your curiosity charged, because this city never sleeps on a dull moment.

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! It's Friday, September 26, 2025, and let me tell you, this city is buzzing like a hotdog stand during marathon weekend. Fall’s crisp energy is in the air—think golden leaves, scarves fluttering, and that magical aroma of cinnamon drifting from every coffee shop on the Magnificent Mile. Today, expect partly cloudy skies in the high 60s, perfect for city adventures whether you’re soaking in art, grooving to live music, or hunting down the quirkiest festival treats.

Now, the fun kicks off early and keeps rolling tonight. For all you live music thrill-seekers, the legendary Mexican rock band Maná lands at the United Center for their “Vivir Sin Aire” Tour. Maná on stage is a hurricane of Latin rock energy, and this show is extra special after that historic Rock and Roll Hall of Fame nomination. Some ticket proceeds go towards empowering Latina entrepreneurs—rock out and do some good!

Craving something a bit more avant-garde? Icelandic group múm, those masters of experimental electronica, play the Gary and Laura Maurer Concert Hall at Old Town School of Folk Music tonight at 8. Expect glitchy beats, dreamy vocals, and otherworldly sounds; bring a curious spirit—your ears will thank you.

The World Music Festival Chicago also continues citywide, with artists from around the globe lighting up stages across 11 venues. If you want a rhythmic passport without leaving the ‘L’ tracks, jump in—these shows are free! Or, for late-night theater nerds, the Neo-Futurists’ Infinite Wrench churns out 30 mini-plays in 60 minutes in Andersonville. It’s like high-speed baseball but with existential jokes instead of home runs.

Families, put your game faces on for Fall Fest at Lincoln Park Zoo. We’re talking pumpkin patches, s’mores, animal encounters—even professional pumpkin carvers crafting gourd masterpieces. Entry to the zoo is free, but you’ll want to budget for caramel apples and maybe a hay ride or two. And if you’re feeling crafty, hop over to Randolph Street Market Festival in the West Loop for vintage finds, live music, and maybe a new fedora to top off those autumn outfits.

And for those of you who like your nightlife with a twist, She’s Crafty—Chicago’s all-female Beastie Boys tribute—turns Schubas Tavern upside down tonight. Hip-hop nostalgia, girl power, and local brews? Boom, perfect Friday.

A quick peek at today’s city scoop: Two hot new restaurant openings. First, an Argentinian steakhouse in River North, reportedly serving up empanadas that make grown men cry with joy. Second, a cozy ramen joint in Wicker Park, where noodle-slurping is not just allowed, it’s required. And heads-up, all you commuters: the CTA Blue Line’s Illinois Medical District stop is your ticket to most big events tonight, with extra trains scheduled—no getting stuck in post-concert car traffic.

No Oly episode is complete without a tip: Locals know that Chicago’s “dibs” system—saving a cherished parking spot with lawn chairs, traffic cones, even barbecues—is both legend and law, especially after a snowfall. But in early fall? It’s tricycle season. Spot a pint-size ride guarding a curb, and you’re witnessing true Chicago innovation.

Before we sign off, here’s something to get you hyped for tomorrow: the Hyde Park Jazz Festival brings smooth grooves to the South Side, HOPtober Fest hops into Wheaton for craft beer aficionados, and families can test their puzzle-solving mettle in the eight-acre corn maze at Pumpkin Daze Fall Festival in Aurora. Don’t miss it, and don’t forget to tune in tomorrow for another wild ride through Chicago’s most epic, offbeat, and unforgettable 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—Ollie Bennet here, the only guide who can name the capital of Lithuania while balancing on a unicycle (it’s Vilnius, by the way). It’s Thursday, September 25, 2025, and the city is buzzing with spicy energy, a dash of adventure, and just a little hint of crisp fall in the air—perfect for that classic debate: deep-dish or thin crust? If you’re stepping outside, expect September sun with a cool breeze, so leave the snow pants at home, but consider that windbreaker unless you want to be mistaken for a windsock along the Lakefront.

Here’s the lowdown on today’s Chicago vibe: The city is prepping for a recipe show-down as the Chicago Gourmet kicks off its first night at Grant Park—so foodies, get stretchy pants ready. Later, the pre-party action is already brewing, with every hotel lobby and bar within smelling distance of Michigan Avenue gearing up for a weekend of culinary chaos. Meanwhile, the artsy folks are still raving about last week’s Chicago Performs festival at the Museum of Contemporary Art, and everyone you meet wants to swap patch sneak peeks from Riot Fest.

Ready for action? Let’s fire off today’s must-do events hotter than jalapeños on a slice at Pequod’s.

Food lovers, this evening is your oyster—Chicago Gourmet is popping corks all weekend at Grant Park, but tonight is the official curtain-raiser. Expect chef demos, local brews, and enough small plates to have you inventing new food groups just to keep up. My advice? Pace yourself, champions. According to GrantParkEvents.com, you can still score entry for tonight.

Prefer night moves? Swing by the Hideout for live indie jams, or catch a concert at one of Chicago’s iconic venues—Chicago-Theater.com has September stacked with everything from chart-toppers to those bands your cousin’s roommate swears will be famous next year.

Bringing the kids? Check the city’s free fall programming: Lincoln Park Zoo is open late, with after-hours animal feedings, and Millennium Park’s splashy playground is still running at full tilt. Mommypoppins.com highlights September as a golden window for zoo visits before everyone starts drinking pumpkin spice out of sippy cups.

If visual feasts are more your thing, cruise through the Driehaus Museum for the Tiffany Lamps: Beyond the Shade exhibit; the glasswork’s so vibrant you’ll need shades just to look at it. Still craving a quirky gem? Don’t forget Wicker Park’s after-dark Storytelling Night—ChicagoStorytelling.com lists a 7 PM show featuring local legends, perfect for a date or solo mission.

Tuning in from a Blue Line stop or running late on the bus? Heads up: The CTA rolled out new improved schedules for rush hour, so even the most seasoned commuters are double-checking platforms today.

Here’s a humid tip direct from the local grapevine: If you want a selfie at Cloud Gate (that’s “The Bean” to us), go on sunrise—less crowd, and you’ll catch the city glinting in gold. Bonus: You’ll look 15% more athletic in every shadow.

Tomorrow, keep your eyes peeled for night markets weaving through Pilsen, more gourmet bites downtown, and the Life Time Chicago Spring Half Marathon—expect road closures, but also a city vibe pumped up on finish-line adrenaline. If you want more wild stories, oddball events, or tales of juggling flaming torches at a Goose Island Block Party, you know where to find me.

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, legendary listeners, to “Things to do in Chicago,” blasting your ordinary Sunday, September 21, 2025, with enough energy to light up every slice of deep-dish pizza from Lincoln Park to South Shore! Oly Bennet here—the world’s quirkiest sports fanatic—and today, I’m on a quest to uncover the wildest, most jaw-dropping happenings in the Windy City.

The vibe right now? Utterly spectacular. It’s early fall with that *just-right* dose of crisp sunshine, perfect for outdoor adventures and festival hopping. The streets are buzzing with post-Cubs game fans flaunting Oktoberfest bratwurst smiles, jazz notes drifting like autumn leaves, and folks power-walking to catch those last rays along the Chicago Riverwalk. According to Chicago Patch’s events calendar, today is officially one for the memory books, with a smorgasbord of culture, music, and spectacular weirdness flooding every block.

So let’s dial it up! For you flavor chasers, don’t miss the Clink & Sip Festival at Morgan MFG from 3–8 pm, hosted by Sip & Empower Foundation. It’s the wine and spirits party of the year, featuring BIPOC makers, bites from award-winning chefs, and enough samples to warrant a shoelace change at sunset. This isn’t just sipping—it’s a community celebration led by Joyce Dawkins and Chrishon Lampley. Raise your glass and cheer for representation!

If your taste runs less grape and more groovy, Bassline is the spot for Reggae Sunday: The #1 Caribbean Party in the city launches tonight at 9:55 pm. This marathon bash brings together global sounds, world-class DJs, live dancers, and Caribbean cocktails—nothing says Chicago in September like sweating it out to afrobeats and reggae rhythms until 2 in the morning.

Family in tow? Take your little explorers to the Uptown Live Street Festival, exploding with live performances, kid-friendly activities, and artist demos on North Broadway. Or check out the Old Town Oktoberfest at 1300 N Wells, serving up polka bands, steins the size of small birds, and the kind of sausage selection that dreams are made of. Theater aficionados get their fix with Remy Bumppo Theatre Company’s “Wish You Were Here” at Theater Wit—don’t just spectate, immerse yourself in Chicago’s dramatic pulse.

As dusk rolls around, chase some culture high notes at the Candlelight Ballet at Thalia Hall or groove through Sinatra Under The Stars at AIRE rooftop. And for you collectors—yes, you with 2000 vinyls under the bed—hit the Chicagoland Record & CD Collectors Show for rare finds and fellow music maniacs.

Now, for Oly’s update on the local scene! Hold your baguettes, because word on the street is a new Parisian-inspired bakery just opened in West Loop—expect lines and croissants so buttery, they come with a public service warning. On transit: the CTA Green Line has added extra trains for weekend festival crowds, so leave the car, grab a Ventra card, and channel your inner commuter superhero.

Can’t decide what to do? Try these must-dos: stroll the Riverwalk for unbeatable sunset views, snap a selfie at Millennium Park’s Cloud Gate (aka the Bean), let loose on the Magnificent Mile, and hunt out eccentric neighborhood pop-ups—Chicago’s mysterious side is alive and thriving. For a hidden gem, bike the 606 Trail at dusk; you’ll see mural magic, food trucks in full force, and locals who’ll give directions with actual enthusiasm.

Local tip for you cool cats: If it rains, duck into the MCA Chicago for mind-bending contemporary art, or grab a jitter juice at one of the city’s indie coffee roasters—Chicagoans are legally required to debate the best roast at least once a week.

Before I let you go, tomorrow’s shaping up wild: look out for rooftop cinema screenings and new gallery pop-ups. I’ll be back with more adventures, so keep those laces tied tight!

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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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

Welcome to Things to Do in Chicago, brought to you by Oly Bennet, your globe-trotting sports nut on the prowl for the city’s quirkiest happenings! It’s Saturday, September 20, 2025—grab your Cubs cap or your Picasso-print umbrella, because Chicago today is a delightful mashup of end-of-summer buzz and fall festival flair. The weather’s mild, sunny with a fun-loving breeze zipping off Lake Michigan—perfect for that just-right blend of shorts-and-light-jacket maneuvering. The city’s streets are alive with laughter, music, and a vibrant art scene pulsing through every neighborhood.

Feeling artsy? The third annual Chicago Exhibition Weekend rolls into its second day, transforming the city into a living gallery with 50 pop-up exhibitions sprawling from Pilsen to Uptown. Expect dazzling installations, surprise performances, and local artists so avant-garde, you’ll swear their paintbrushes attended improv classes with Second City. Choose Chicago says this is the place to soak up that creative spirit and maybe score a selfie with something abstract.

Jazz lovers, it’s your moment! Hamilton Park hosts the final day of the Englewood Jazz Festival, spotlighting the 60th anniversary of Chicago’s own Association for the Advancement of Creative Musicians. Ernest Dawkins leads the charge, unleashing wild sax riffs and the relentless beat of jazz that’s experimental and soulful—bring a picnic blanket and join the musical movement that made Chicago the unofficial jazzy planet in the solar system.

Soccer fanatics and family adventurers can sprint to Logan Square for The Messi Experience, an immersive soccer extravaganza dedicated to Lionel Messi. Imagine interactive exhibits mixed with the sneakerhead energy of ESPN meets Messi’s magic—plus exclusive murals from local graffiti wizard Kane One. Snap a photo with the Messi mural and debate with your crew: was Messi’s left foot ordained by the soccer gods, or is he just allergic to walking?

If you want more festival fever, swing by Old Town Oktoberfest and raise a stein in Chicago’s first German neighborhood. There’s bratwurst, oompah bands, and a dance floor just daring you to invent a new move called the “Loop Line Shuffle.” If you can still walk straight afterward, make tracks to the Summer’s Last Dance Music & Arts Festival in the southwest, where DJs spin, artists paint, and every food truck battles for your undying burger loyalty.

For those seeking high culture, the Museum of Contemporary Art is running Chicago Performs—a wild showcase of live contemporary dance, shadow puppetry, and communal rituals. Helen Lee’s movement exhibit even includes sound bowl workshops and guided walks to the lake, proving Chicago’s not just about deep dish; it’s about deep feels.

Now, for fresh scoops: Small business lovers can mingle at today’s Chicago Small Business Expo in Lincoln Park. Watch for Boba Break’s grand opening on Clark Street—it’s rumored the bubble tea is so good, it’ll have you humming “Sweet Home Chicago” after every sip. The CTA reminds everyone that red line service downtown now runs every 6 minutes—so hop on and get exploring.

Must-do tip from Oly: If you want a true Chicago memory, grab a Divvy bike and ride along the Lakefront Trail at sunset. You’ll get jaw-dropping skyline views, waterfront breeze, and possibly a goose photobomb. Locals know this is Chicago’s free roller coaster, minus the fear of dropping your hot dog.

Fun fact to impress your friends: The city invented the Ferris Wheel for the 1893 World’s Fair. That’s right—next time you see Navy Pier’s wheel, thank Chicago for putting a spin on history!

Feeling hungry for more? Tomorrow, watch out for Czech Heritage Week events and another round of wild art at Chicago Exhibition Weekend. Don’t miss our next episode—Oly Bennet will dig up more sparkling sports, sideshows, and festival shenanigans.

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