Chicago News and Information

Welcome, listeners, to Things to Do in Chicago for Friday, January 9, 2026. I’m your globe-trotting sports nut Oly Bennet, and today the Windy City feels like a chilly-but-game-day-ready locker room: cold temps, crisp air off the lake, and just enough winter sunshine to make you say, “Yeah, I can totally handle this… if there’s hot chocolate involved.”

Let’s kick off with today’s vibe. Indoor culture and outdoor ice are tag-teaming the city. Third Coast Review notes that ice skating at Millennium Park and Maggie Daley Park is running through the season, so expect bundled-up crowds carving wobbly...

Welcome, listeners, to Things to Do in Chicago with your globe‑trotting sports nut pal, Oly Bennet! It’s Thursday, January 8, 2026, and the Windy City is rocking that classic deep‑winter energy: cold enough to see your breath, but hot enough in spirit to melt the lakefront. January here means layers, beanies, and a whole lot of “we’re going out anyway.”

According to Time Out Chicago, the big mood‑setter this month is the Tomorrow Never Knows 2026 festival, kicking off today and running weekends all January, taking over indie hot spots like Lincoln Hall, Schubas, Metro, the Hideout, and R...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut diving into the Windy City's wildest vibes on this crisp winter Sunday. Chicago's buzzing with that post-holiday glow—think chilly winds around 25 degrees Fahrenheit, flurries dancing like they're auditioning for a snowball fight, and the energy high from New Year's resolutions turning into rink-side cheers.

Kick off your day with family fun at Navy Pier's Winter WonderFest, wrapping up today with thrilling rides like the Cliffhanger and Zero Gravity, ice skating on the Verizon Google Pixel rink, and a massive 42-foot holiday tree—perf...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut diving into the Windy City's wildest winter vibes on this chilly Saturday. Picture crisp air around 25 degrees Fahrenheit with flurries dancing over the skyline—perfect for cozy indoor thrills and frosty outdoor fun as we shake off the new year haze.

Kick off your day with these hot picks: Families, hit Navy Pier's Winter WonderFest wrapping up today with indoor ice skating, rides, and festive lights in Festival Hall. Culture lovers, craft Three Kings Boxes at the National Puerto Rican Museum from 10:30 a.m...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut diving into the Windy City's wildest vibes on this crisp Friday, January 2, 2026. Picture this: chilly winter air around 25 degrees Fahrenheit with light flurries dancing like quirky snow athletes, buzzing from New Year's fireworks echoes—pure electric post-holiday magic!

Kick off your day with these hot picks covering every thrill: Catch the Chicago Bulls slamming Orlando Magic at United Center tonight at 7 PM—hoops fever that'll have you jumping like a slam-dunk champ, per United Center schedules. Families, slide into Winter Wonderfest at Navy Pier...

Welcome to Things to Do in Chicago, listeners! It's January 1st, 2026, and we're kicking off the new year in one of America's most electrifying cities. The vibe today? Pure celebration energy! Chicago just wrapped an unforgettable New Year's Eve with crowds flooding the Chicago Riverwalk to ring in 2026, and that festive momentum is absolutely carrying into today.

Let me hit you with some fantastic happenings right now. First up, Winter WonderFest at Navy Pier is in full swing, and this is pure magic for all ages. We're talking a dazzling 42-foot Holiday Tree, thrilling rides like the Cliffhanger...

Welcome, listeners, to Things to Do in Chicago with your globe-trotting sports nut pal, Oly Bennet! It’s Sunday, December 28, 2025, and the Windy City is in full cozy-winter-hustle mode: chilly temps, holiday lights still glowing, and just enough lakefront breeze to make you question your life choices if you forgot a scarf.

Let’s fire off today’s vibe check. Downtown, The Chicago Theatre is wrapping up its run of ’Twas the Night Before… by Cirque du Soleil, with performances this afternoon at 1 and 4 p.m., turning 175 North State into a flying-reindeer-meets-elite-acrobatics playground, according to The Chicago Theatre’s event list...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned city explorer, buzzing with energy on this crisp winter Saturday, December 27, 2025. Chicago's vibe is pure post-holiday magic—think chilly winds whipping off Lake Michigan around 30 degrees Fahrenheit, snow-dusted streets glowing with leftover lights, and that electric hum of folks shaking off Christmas into New Year's prep.

Kick off your day with family fun at Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall. Glide on the ice rink, conquer the Cliffhanger ride, bounce on slides, and snag a Centennial Ferris Wheel sp...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday hype machine, and today we're diving into the Windy City's post-Christmas glow on this crisp Friday, December 26th. The vibe? Pure winter magic—chilly temps around 30 degrees with flurries dancing like they're late for a snowball fight, but indoors it's all twinkly lights and festive cheer keeping the holiday spirit alive.

Kick off your day with family thrills at Navy Pier's Winter WonderFest, open from 10 AM with rides, ice skating, bumper cars, and a massive holiday tree—perfect for kids under 46 inch...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday hype man, ready to unleash the magic on this festive December 25, 2025. Chicago's vibe today is pure winter wonderland—crisp snow-dusted streets, twinkling lights everywhere, and that cozy holiday hum with families bundling up against the chill for Christmas cheer.

Kick off your day with Pink Martini's jazzy New Year Celebration Tour at the Auditorium Theatre, where the All-Stars deliver a sparkling Season of Stars show packed with eclectic tunes that'll have you swaying like a snowflake in the Windy City breeze. Fa...

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut pal, Oly Bennet! Chicago is buzzing today with full-on winter energy: chilly air, holiday lights everywhere, and the kind of lakefront breeze that makes your coffee work overtime. Bundle up, because this city plays hard in all four seasons.

Let’s kick off with today’s highlight reel. Over at Navy Pier, Winter WonderFest is in full swing, turning Festival Hall into an indoor snow globe of rides, ice skating, bounce houses, bumper cars, and even a ticket that scores you a ride on the Cent...

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennett, coming to you on Friday, December 19, 2025. Chicago’s in peak winter wonderland mode right now: cold, crisp, and perfect for bundling up, grabbing a hot chocolate, and pretending you’re in your own holiday movie montage along the lakefront.

Let’s lock in today’s vibe. Holiday season is in full sprint, the Loop is glowing, and neighborhoods are twinkling with lights. Over at the Chicago Theatre, Cirque du Soleil’s “’Twas the Night Before…” is back tonight, dazzling State Street with acrobatics and festive chaos...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday hype man, and today, Thursday, December 18th, Chicago's buzzing with that crisp winter magic—think chilly winds whipping off Lake Michigan around 30 degrees Fahrenheit, perfect for bundling up and diving into festive fun that feels like an epic polar adventure.

Kick off with **Cirque du Soleil's 'Twas the Night Before** at The Chicago Theatre tonight at 7 PM, where acrobats and reindeer flip holiday cheer into jaw-dropping flips—Chicago Theater calls it their 49th original stunner running through December 28th. Families, hit **Seni...

Welcome to Things to Do in Chicago, listeners! I'm Ollie Bennet, your globe-trotting sports nut turned holiday adventure guide, buzzing with energy on this crisp winter Sunday. Chicago's vibe today is pure festive magic—think twinkling lights, a chill in the air around 30 degrees with possible flurries, and that electric holiday hum as families bundle up for indoor thrills.

Kick off with Navy Pier's Winter WonderFest, open from 10 AM in Festival Hall—rides like the Cliffhanger and Zero Gravity, ice skating on the Verizon Google Pixel rink, a 42-foot holiday tree, and Ferris Wheel spins for all ages, perf...

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennet, coming to you on Saturday, December 13, 2025. The city’s in full winter-showoff mode: cold, crisp lakefront air, holiday lights everywhere, and just enough wind to make you question your life choices if you forgot a hat.

Today’s vibe? Pure festive chaos. Navy Pier’s Winter WonderFest is in full swing with indoor rides, an ice rink, and a ticket that even includes a spin on the Centennial Wheel, turning Festival Hall into a giant snow globe of screaming kids and secretly-thrilled adults, accord...

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut Oly Bennet, coming at you on Friday, December 12, 2025. The city’s in peak winter-holiday mode: cold enough for cozy layers, but perfect for twinkling lights, hot drinks, and maximum Chicago swagger.

Here’s the vibe today: downtown is buzzing with shoppers and office parties, the lakefront is brisk but beautiful, and the Loop is glowing with holiday lights and market stalls. Navy Pier’s Winter WonderFest, according to Navy Pier, is in full swing with indoor rides, ice skating, and a 42-foot holiday tree inside Festiv...

Welcome, listeners, to Things to Do in Chicago with your globetrotting sports nut buddy, Oly Bennet. Chicago is buzzing today with classic winter-in-the-city energy: chilly temps, big coat weather, and that perfect excuse to power-walk like you’re in your own sports montage along the lakefront.

Let’s kick off with today’s vibe-setters. Over at The Chicago Theatre, Cirque du Soleil brings holiday acrobat chaos in the best way with “’Twas the Night Before…” tonight at 7 p.m., turning State Street into a festive circus playground, according to Madison Square Garden Entertainment. Up in Wrigleyville, Winterland at Gallagher Way...

Welcome, listeners, to Things to Do in Chicago! I’m Oly Bennett, your globe-trotting sports nut turned Windy City hype man, coming to you on this crisp December Sunday with Chicago buzzing in full holiday mode. The lakefront air is cold and sharp, perfect for scarves, hot chocolate, and pretending your power walk down Michigan Avenue qualifies as a winter sport.

Today the city is a mash-up of cozy, sparkly, and downright rowdy. Over at United Center, the Chicago Bulls take on the Golden State Warriors tonight, turning the West Side into a slam-dunk circus of noise and na...

Welcome listeners to Things to Do in Chicago with your globetrotting sports nut pal, Oly Bennett. Chicago this December Saturday is serving classic Midwest winter vibes: cold enough to see your breath, perfect for cozy lights, indoor fun, and a little lakefront braving if you’ve packed your big coat.

The city’s energy today is pure holiday hustle. Navy Pier is in full festive beast mode with Winter WonderFest, running now through early January, turning Festival Hall into an indoor playground of rides, ice skating, a 42‑foot holiday tree, and a ticket that even includes a ride on the...

Welcome, listeners, to Things to Do in Chicago for Friday, December 5, 2025. It’s your globe-trotting sports nut pal, Oly Bennet, coming to you from the shores of Lake Michigan, where the wind is spicy, the lake is moody, and the city is fully in holiday hustle mode. Picture chilly temps, big coats, and that perfect combo of twinkling lights and visible breath as you step outside.

Today’s vibe is pure festive grind. Holiday markets are buzzing, trains are packed with puffy jackets, and everyone’s balancing office life with “just one more” seasonal outing. Think hot chocolate in one han...

Welcome back to Things to Do in Chicago, where your favorite globe-trotting sports fanatic brings you the absolute best happenings across this incredible city. I'm your host, Ollie Bennett, and let me tell you, it's Thursday, December 4th, 2025, and Chicago is absolutely buzzing with holiday magic and unbridled festive energy.

Today the Windy City is living up to its name with that classic December chill, but don't let that stop you because the holiday spirit is cranked up to eleven. We're talking lights, music, ice skating, and enough seasonal cheer to make even the most cynical sports enthusiast...

Hey there, listeners! Welcome to Things to Do in Chicago! I'm your host, Ollie Bennett, and boy do we have a Sunday lined up for you today, November 30th, 2025. Let me tell you, the Windy City is buzzing with energy right now, and I'm absolutely pumped to walk you through the best ways to spend your day!

First, let's talk vibe. It's a crisp late November Sunday in Chicago, and the city's got that perfect blend of fall energy mixed with early holiday season excitement. You can feel it in the air—people are out, events are happening, an...

Hey there, listeners! Welcome to Things to Do in Chicago, where we're catching you up on all the action happening in the Windy City today, Saturday, November 29th, 2025. If you're in Chicago right now, you've picked one heck of a day to be here because this city is absolutely buzzing with energy and there's something for absolutely everyone.

Let's jump straight into the main events lighting up Chicago today. First up, if you're a music fan, Straight No Chaser is bringing their Holiday Road Tour to the Chicago Theatre tonight. These guys are hilarious and their holiday shows...

Welcome, welcome, WELCOME to Things to Do in Chicago, friends! I'm your host Ollie Bennett, and boy oh boy, do we have a spectacular Friday lined up for you on November 28th, 2025!

Right now, the Windy City is sitting pretty at a chilly 34 degrees with mostly cloudy skies—perfect hoodie weather, my friends. But here's the kicker: we're about to get absolutely WALLOPED by one of the biggest snowstorms Chicago has seen in years tomorrow, so today is your golden ticket to get outside and soak up the relatively calm vibes before the white stuff descends like an av...

Welcome to Things to Do in Chicago, your daily guide to the Windy City's most incredible happenings! I'm your host, Ollie Bennett, and let me tell you, today is Thursday, November 27th, 2025—Thanksgiving Day—and Chicago is absolutely buzzing with energy despite the holiday vibe!

The city's got that perfect autumn chill in the air, you know that crisp Thanksgiving morning feeling where everyone's either cooking up a storm or getting ready for something spectacular. Speaking of spectacular, we've got some absolute bangers happening today that'll make your Thanksgiving unforgettable!

First up, the CBS Sports Thanksgiving Clas...

Welcome to Things to Do in Chicago! It's Monday, November 24, 2025, and Oly Bennet here, coming at you live from the heart of the Windy City, where the vibe today is brisk, bold, and bursting with energy. Overnight rain left the streets glistening, and at this very moment, Chicago is shaking off the cold with the kind of spunk only this city can muster. As the city gears up for Thanksgiving, the air is buzzing—almost as much as my sense of adventure!

So, what's setting the tone in Chicago today? Holiday lights are officially dazzling the skyline, the an...

Welcome, listeners, to Things to Do in Chicago! It’s Friday, November 21, 2025, and the city is buzzing louder than the vendors at Wrigley selling hot dogs. Oly Bennet here, your globe-trotting, sports-loving, quirky-comp-meter is dialed to max curiosity, ready for today’s Chicago adventure. Whether you’ve already braved the early chill or you’re just shaking off your morning hibernation, the city is a dazzling mash-up of holiday cheer and big-league energy.

Today, Chicago’s got that crispy, late fall edge—think brisk wind, steamy coffee, and the distant sound of skates gliding across Millennium Park. According to local new...

Welcome, fellow thrill-seekers and adventure hounds, to Things To Do in Chicago—your daily passport to fun, oddball, and downright dazzling events across the Windy City! It’s Thursday, November 20, 2025, and if Chicago could strut, it’d be doing the Charleston this morning. We’ve got that crisp autumn air, leaves twirling down the river walk, and a city absolutely buzzing with pre-holiday energy.

Today’s weather? Classic November in Chicago—jacket highly recommended! It’s brisk, but with those blue skies and golden hour sunlight giving downtown a little extra glimmer. Folks are already snapping selfies at Millennium Par...

Welcome to Things to Do in Chicago! I’m your tour guide of tomfoolery, Oly Bennet—your globetrotting sportster dropping in on the Windy City for a mashup of marvels, music, and moxie. Today is Sunday, November 16, 2025, and let’s just say the city’s in full pre-Thanksgiving swing, bursting with energy as crisp as the autumn air. The weather’s toggling between “bring a jacket” brisk and “no, seriously, winter is coming,” but Chicagoans don’t slow for a little cold—they rev up!

Now, what’s shaking around town? The Chicago Artisan Market in Fulton Market is whirling open its doo...

Hello Chicago explorers and quirky competition lovers! It’s Oly Bennet here, your globe-trotting sports nut—broadcasting straight from the heart of the Windy City on this fine and brisk Saturday, November 15, 2025. Bundle up, listeners: the autumn air’s a little nippy, but that’s never kept Chicago down! The city’s buzzing with both big events and unexpected gems that’ll have you grinning wider than a deep dish pizza slice.

Let’s set the scene: Under a skyline punctuated by more cranes than a World Cup opening ceremony, the mood today is downright electric. The holidays are sneaking i...

Welcome, you fabulous crew of adventure-seekers, to Things to Do in Chicago! It’s Friday, November 14, 2025, and right now, the Windy City’s buzzing with electric energy—the kind that has folks swapping scarves for selfie-sticks and plotting their next deep-dish encounter. If you just peeked out your window, you know it’s classic autumn—crisp, cool air, flashes of gold in the parks, windy enough to make you feel like you’re auditioning for Chicago’s next marathon. As for city happenings, today is the launchpad for epic events, wild stories, and maybe, just maybe, a taste of the world’s quirki...

Welcome to “Things to do in Chicago”, listeners! Today is Thursday, November 13, 2025. Ollie Bennet here, bursting with energy from the heart of the Windy City—where November’s brisk air is making scarves Chicago’s hottest accessory. The city is alive with orange leaves, holiday prep, and enough quirky events to keep your laugh muscles flexed until spring.

Right now, Chicago’s weather is textbook fall: chilly winds, highs hovering around 45°F, so bundle up and charge into the day! The city’s vibe is festive—the Millennium Park Christmas tree is about to sparkle, the Magnificent Mile’s lights are lighti...

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...

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 Magazi...

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...

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 stac...

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...

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 Sne...

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 transfo...

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...

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 nocturn...

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.
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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 buzzin...

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 Michi...

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...

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 adventur...

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...

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...

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 Pa...

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...

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...

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...

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 turn...

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...

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 fu...

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 tha...

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’r...

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 fro...

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 al...

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...

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...

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 roll...

Welcome, listeners, to “Things to do in Chicago!” Today is Friday, September 19, 2025, and I’m your host, Oly Bennet—the only sports nut who knows more about competitive cheese-rolling than football. But don’t worry, I’m also here for the art, music, and that legendary Chicago pizza (trust me, deep dish is basically an endurance event). The city’s in its autumn groove—there’s a crispness in the air, a gentle breeze off Lake Michigan, and everyone’s swapping summer shades for team scarves. The sun’s breaking through, making this Friday absolutely perfect for some adventures.

What’s the vibe...

Welcome, thrill-seekers and adventure-lovers, to Things to do in Chicago! It’s Thursday, September 18, 2025, and Oly Bennet here, your jetsetting mischief-maker on a quest to uncover the quirkiest, coolest, and wildest happenings in the Windy City. The streets are buzzing, leaves are hinting at autumn, and today we’ve got sunshine with just enough of that classic Chicago breeze to keep you on your toes.

Let’s set the scene: the city is alive with legendary music, global art, family festivities—and a little K-Pop magic thrown in for good measure. Whether you’re a jazz hound, an art aficio...

Welcome to Things to Do in Chicago! It’s Sunday, September 14, 2025, and your pal Oly Bennet is here, fresh off a plane from chasing cheese in Gloucestershire, ready to dive into the epic, electric vibe of Chicago today. Picture this: it’s a classic Windy City evening with a hint of fall crispness, a touch of lake breeze ruffling your hair, and a whole city primed for adventure like you’re about to set a world record in urban exploring.

Let’s jump into the action! Today, Chicago’s bustling with events—there’s something for every mood, whether you’re...

Welcome, listeners, to “Things to do in Chicago!” I’m Oly Bennet, and today is Saturday, September 13, 2025. The Windy City is showing off some classic late-summer flair: think temps hovering in the mid-70s, sunshine poking around puffy clouds, and breezes just right for an outdoor adventure—or a slice of deep-dish on a patio. Chicago is buzzing with event mania, with everything from art explosions and foodie feasts to epic football and flower power.

If your soul craves a gallery fix, jet over to Millennium Park for Franz West’s monumental installations—imagine giant abstract sculptures turning selfies into...

Welcome, brilliant listeners, to Things to Do in Chicago with your adventure-obsessed host, Oly Bennet! Today is Thursday, September 11, 2025, and if you’re feeling the Chicago buzz, you’re not alone. The Windy City is absolutely shimmering with late-summer energy—think breezy lakefront strolls, rooftops packed with Cubs fans reliving last night’s homer, and the sweet scent of street food promising delectable detours. Skies today are mostly clear, so grab your sunglasses—unless you fancy a surprise cameo on the local weather report catching treats from a rogue food truck.

Hold onto your berets and beanies, because tonight’s...

Welcome, listeners, to Things to Do in Chicago! Today’s date is Sunday, September 7th, 2025, and I’m your energetic tour guide Oly Bennet, globe-trotting sport fanatic and explorer of all things wildly wonderful. Here in Chicago this morning, the city is buzzing with late summer vibes—think sunny skies, a little breeze off Lake Michigan, and crowds everywhere gobbling up fun like deep-dish pizza.

Grant Park is absolutely in party mode because it’s the grand finale day of the Taste of Chicago festival. If you’ve never seen this, imagine food trucks lined up like a parade, ar...

Welcome, listeners, to Things to do in Chicago with your globe-trotting, sport-spotting, always-laughing host Oly Bennet! It’s Saturday, September 6th, 2025, and the Windy City’s buzzing louder than a vuvuzela at a Quidditch match! The skies today are serving up sunshine with just a dash of that classic Lake Michigan breeze—truly perfect weather for adventures on foot or by kayak, maybe even a bit of competitive goose watching if you’re into that sort of thing.

Today, Chicago’s cranking up the fun-o-meter with a spectacular lineup. For the culture vultures, Millennium Park has gone all avant-gard...

Good morning, Chicago! Welcome to “Things to Do in Chicago” on Thursday, September 4, 2025. The city is greeting you with classic early fall energy—a crisp breeze off the lake, pleasantly cool highs around 70°F, and mostly clear skies overhead. With air quality looking good and a post-Labor Day buzz in the air, Chicago’s streets are teeming with anticipation for today’s events and the weekend ahead[1][8].

Let’s dive into today’s top happenings across Chicago:

- Career seekers, take note: The 25th Annual Diversity Employment Day Career Fair kicks off at 11am at Courtyard Chicago Downtow...

Welcome to “Things to Do in Chicago,” your go-to guide for city adventures on this beautiful Sunday, August 31, 2025! Whether you’re a lifelong local or just passing through, today’s lineup proves the Windy City is anything but ordinary.

Chicago is waking up to *perfect late-summer weather*, with **mild temperatures in the low 70s, plenty of sunshine, and a hint of warmth that makes outdoor plans irresistible**[7][2]. The friendly skies set a laid-back, festive tone, while clear air invites everyone to get outside and enjoy a breath of fresh city life.

Wondering what’s happening around town today...

Welcome to "Things to do in Chicago," your go-to guide for making the most out of the Windy City on this beautiful Saturday, August 30, 2025! Whether you're a local or just passing through, there’s an electric energy pulsing through Chicago today, and the city feels alive with anticipation for Labor Day weekend.

Let's set the scene: This morning brings **mostly cloudy skies** with a touch of sun peeking through, highs dancing in the low 70s, and only a small chance of stray showers—ideal for exploring neighborhoods, hanging outdoors, or heading to the lakefront[2]. The air feels fresh and...

Welcome, listeners, to “Things to do in Chicago!” It’s Friday, August 29, 2025—the start of Labor Day Weekend in the Windy City. The summer sun is shining, temperatures are comfortably in the mid-70s, and the air quality is excellent. Chicago feels alive and festive, with a weekend packed full of music, art, and cultural celebrations.

Today, Chicago buzzes with events that cater to every taste. Kicking off the festivities is the Taste of Polonia Festival in Jefferson Park, starting at 5:00 p.m. This four-day event is perfect for families and foodies alike, with nonstop live music, dance performa...

Welcome to Things to Do in Chicago! It’s Thursday, August 28, 2025, and the city is buzzing with summertime energy. The weather today is classic late August—expect highs in the upper 70s, ideal for both indoor and outdoor adventures. Air quality is good, and the city feels lively and celebratory as Chicagoans make the most of these warm days before autumn sets in.

Starting with today’s event highlights, there’s truly something for everyone:
- Music lovers should not miss the opening day of the Chicago Jazz Festival, kicking off at 12:00 PM with free performances in Grant Pa...

Welcome to “Things to Do in Chicago” for Sunday, August 24, 2025—your front-row seat to the city’s best happenings and insider thrills! Whether you’re a lifelong local or a first-time visitor, today Chicago buzzes with vibrant energy, sunny weather, and a true festival feeling as summer wraps up.

Snapshot of today’s vibe: Skies are clear this morning, with temperatures gently easing into the mid-70s—perfect for exploring outdoors. Air quality is in good shape, thanks to city efforts after a stretch of hazy days. With the weekend in full swing, bustling crowds are flocking to the lakefront...

Welcome to “Things to Do in Chicago,” your go-to guide for exploring the Windy City on Saturday, August 23, 2025! Whether you’re a longtime local or a first-time visitor, get ready for an exciting day packed with art, music, delicious food, and Chicago’s one-of-a-kind summer spirit.

Starting off, Chicago is buzzing this Saturday under warm late-summer skies—expect temperatures in the upper 70s, perfect for both indoor and outdoor adventures. Air quality is in the “good” range, so breathe easy while you make the most of the city. The overall mood is lively, with crowds gathering for major festivals and...

Welcome to Things to Do in Chicago! It’s Friday, August 22, 2025, and the city is glowing with late summer energy—perfect weather for celebrating outdoors, with temperatures comfortably in the mid-70s and air quality rated as “Good,” making it ideal for exploring every corner of the Windy City.

Before diving in, here’s your snapshot of Chicago today: locals are gearing up for a packed weekend, from world-class music fests to neighborhood celebrations and global flavors. The excitement from last night’s storms has cleared, revealing blue skies and a light lake breeze. That’s your cue to head outsid...

Welcome to “Things to do in Chicago” for Thursday, August 21, 2025! Whether you’re a longtime local or just visiting for the day, we’re here to guide you through the best of the Windy City.

Today, Chicago is buzzing with late-summer energy. The weather is warm with a soft lake breeze—perfect for outdoor fun. Air quality is in the healthy range, and the streets are filled with anticipation for tonight’s events and a spectacular fireworks finale[1]. In the harbors, a “No Wake Zone” is in effect for boaters due to the highly anticipated Chicago International Boat Show, so expect...

Welcome to “Things To Do in Chicago” for Saturday, August 16, 2025! Whether you’re a local looking to spice up your day or a visitor ready to dive into the Windy City’s pulse, we’ve got today’s must-see events, cultural highlights, and local news—plus tips to make the most of Chicago’s summer scene.

First, let’s set the vibe: It’s a classic August day with balmy summer weather, making it prime time to be outside. The air quality is moderate and ideal for strolling along the lakefront, and there’s a buzz in the city thanks to one of...

Welcome to Things to Do in Chicago for Friday, August 15, 2025! The city is buzzing with **summer energy**—skies are mainly clear, the temperature is in the low 80s, and a fresh breeze is sweeping in off the lake, making it the perfect day to explore. Air quality is good, so leave the car behind and get out on foot or bike to soak up the city’s unbeatable late-summer spirit and vibrant neighborhood scene.

Let’s dive into some of today’s top happenings across Chicago:

- **Taylor Street Little Italy Festival** kicks off this evening at 5:00...

Welcome to “Things to Do in Chicago” for Thursday, August 14, 2025! It’s a bright, late-summer morning in the Windy City. As the sun rises over Lake Michigan, Chicago feels buzzing—clear skies in the forecast, warm temperatures (low 80s), and good air quality promise an ideal day for adventures across town. The city is alive with food, music, and culture, setting the perfect tone to get out and explore.

Let’s dive into today’s top happenings:

- For lovers of food and true Chicago heritage, the **Taylor Street Little Italy Festival** kicks off tonight at 5 p.m. The his...

Welcome to Things to do in Chicago, your essential city guide for Sunday, August 10, 2025! As the sun rises over the Windy City, locals and visitors are buzzing with summer energy. Today’s weather is warm and welcoming, perfect for exploring, though always check for updates if severe conditions pop up. Air quality is holding steady, and the city feels alive after yesterday’s Bud Billiken Parade, which drew thousands to celebrate Black youth and kick off the back-to-school season[2].

Let’s jump into today’s top happenings:
- Northalsted Market Days is rocking the Lakeview neighborhood from 11am to 10...

Welcome to “Things to Do in Chicago!” It’s Saturday, August 9, 2025, and there’s no better place to be than the Windy City. Today’s summer weather is living up to expectations—warm temps in the low 80s, perfect for getting out and exploring. Air quality is good, and the city buzzes with visitors and locals enjoying street festivals, vibrant parks, and lakefront fun.

Kicking off your day, why not check out some of Chicago’s standout events? For foodies and families, Veggie Fest returns to Lisle, just outside the city, with free admission, free parking, and all things plant-b...

Welcome listeners to “Things to do in Chicago”—your essential guide to all the action happening in the Windy City! Today is Friday, August 8, 2025, and if you’re waking up in Chicago, you’ll notice a classic late-summer vibe: city streets are buzzing with festival anticipation, blue skies are peeking through after this week's rain, and the Lake Michigan breeze brings some welcome relief as humidity dips. While cleanup continues in areas hit hard by last month’s flooding, events across the city are back in full swing, and the air quality is currently good, making it a great day to get outsi...

Welcome to "Things to do in Chicago"! Today is Thursday, August 7, 2025, and the Windy City is buzzing with summer energy. The weather is classic August—warm, a bit humid, and perfect for outdoor adventuring. If you're heading out, pack sunglasses and sunscreen. Air quality is generally good, though monitors are on the lookout for haze drifting in since wildfires west of Chicago caused visibility issues earlier in the week[2].

Chicago is alive with cultural happenings, music, and opportunities for everyone today. Here’s your snapshot of the city’s vibe:

First up, music lovers should not miss t...

Welcome to “Things to Do in Chicago,” your go-to guide for what’s hot in the Windy City! Today is Sunday, August 3, 2025, and Chicago’s summer spirit is in full swing, despite lingering haze as air quality alerts continue following a lively Lollapalooza weekend[2]. With the city bathed in August warmth, the streets buzz with locals and visitors soaking up every bit of sunshine.

Let’s dive into today’s key happenings across town, promising something for everyone. Start your morning at the Ruth Page Center for the Arts’ free, all-ages Open House from 10 a.m., where dance, movement, and...

Welcome to “Things to Do in Chicago” for Saturday, August 2, 2025! Whether you’re a local or just visiting, we’ve gathered the best ways to soak up the city’s buzz this weekend.

Chicago’s got that festival energy today. It’s a blue-sky Saturday, perfect for exploring—though some are noting the city’s notorious air quality, so if you’re sensitive, you might want to keep outdoor adventures brief[2]. But mostly, expect cooling breezes, crowds with big summer smiles, and a unique blend of art, music, and city life.

Let’s kick off with today’s can’t-miss hap...

Welcome to "Things to do in Chicago" for Friday, August 1, 2025! Whether you’re a long-time Chicagoan or just in town for the weekend, get ready for a day packed with excitement, summer rhythms, and iconic city charm.

Chicago has an unmistakable energy this morning. Expect **warm, sunny weather with just a hint of that famous lake breeze**—a perfect summer day in the city. The air quality is good, and Grant Park is buzzing as crowds gather for the first full day of **Lollapalooza 2025**, setting the pace for an electric weekend of music and festivals[4][5]. If live music isn’...

Welcome to “Things to Do in Chicago” on this Thursday, July 31, 2025! As you start your day, grab an umbrella—Chicago is waking up to morning showers with temperatures in the comfortable mid-70s, hitting a high of 74°F as the skies are expected to clear later in the afternoon[2][10]. The air feels fresh after the rain, giving the city a crisp, rejuvenated vibe—the perfect backdrop for both outdoor and indoor adventures.

Let’s take a quick pulse on the city: downtown is lively with anticipation as Chicago gears up for a busy day. With the air clear and a sligh...

Welcome to “Things to Do in Chicago!” It’s Sunday, July 27, 2025, and the city is buzzing with excitement as we coast through the heart of summer. Storms just brought record rainfall a few days ago, leaving the air feeling fresh and the city’s greenery vibrant—though a few streets still show signs of the recent flash flooding[2]. Overall, the weather today is warm and comfortable, the perfect Chicago day for exploring neighborhoods and discovering something new.

Here’s a quick look at the city’s mood: people are out and about, soaking up summer vibes, while clean-up crews wrap up...

Welcome to “Things to do in Chicago” for Sunday, July 27, 2025! Whether you’re a local or a visitor, we’re here to help you make the most of your day in the Windy City.

After a weekend of powerful thunderstorms and record rainfall that brought flash flooding to parts of the city on Friday, Chicago is shaking off the wet weather and buzzing with energy as festival season peaks. Be sure to keep an umbrella handy—while the skies are mostly clearing, some spots may still have standing water and scattered showers in the forecast[2][8]. The city feels vibrant, f...

Welcome to “Things to do in Chicago” for Saturday, July 26, 2025! If you’re looking to soak up the city’s electric summer energy, you’re in the right place. Today, Chicago feels both vibrant and unpredictable: while highs hover around a muggy 86°F, the city’s still drying out from yesterday’s epic rain—over six inches in just two hours in parts of the metro area brought flash flooding, so streets may still be slick and caution is advised if you’re out and about[2][5].

Let’s dive into today’s must-see events, with a little something for everyone:
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Welcome to “Things to Do in Chicago” for Friday, July 25, 2025! The city is buzzing as we roll into another vibrant summer weekend. With the sun peeking through after last night’s storms and a heat advisory still in effect, today promises plenty of energy, warm breezes, and a jam-packed slate of happenings across the Windy City[5][8]. Remember to dress light, stay hydrated, and keep an eye on the forecast, as the weather’s a true classic: hot, with a mix of Midwest humidity and sunny breaks.

Kicking things off, here are some of today’s standout events to match ever...

Welcome to “Things to Do in Chicago!” Today is Thursday, July 24, 2025, and the city is buzzing despite an intense summer heat wave gripping the Midwest. With a “feels like” temperature soaring well into the upper 90s, Chicagoans are beating the heat by flocking to both open-air celebrations and delightfully air-conditioned venues. As a reminder, keep cool, hydrate, and take it easy outdoors, as local meteorologists have issued heat advisories with a possible storm threat later in the day[2][5].

Let’s dive into the top happenings around town:

First, toast National Tequila Day with style! Selva Rooftop at The Emi...

Welcome to “Things to do in Chicago” for Sunday, July 20, 2025! It’s a sunny mid-July morning and Chicago is buzzing with summer energy. Today, the skies are mostly clear, and the air quality is good—perfect for exploring the city’s neighborhoods, lakefront, and vibrant festival scene.

Today’s highlight is the World Fair US at SeatGeek Stadium, one of Chicago’s most exciting international festivals running now through July 28. Starting at 3 pm, you can stroll among six regional pavilions representing over 80 countries—sampling global cuisine, shopping handmade crafts, and catching music and dance performances from every corner of the world. It...

Welcome to “Things to Do in Chicago” for Saturday, July 19, 2025! It’s a bustling summer day in the Windy City, and whether you’re a lifelong local or just visiting, there’s an adventure waiting around every corner.

Let’s set the scene: as of this morning, Chicago is alive with anticipation for some strong to severe storms rolling in later, so pack an umbrella if you head out. Despite the weather, the city’s spirit is as lively as ever, with energy pulsing through its neighborhoods thanks to a weekend lineup packed with food, music, and fun[2][8].

Her...

Welcome, Chicago enthusiasts, to “Things to do in Chicago” for today—Friday, July 18, 2025! The city is in full swing under warm, lively mid-July skies. You’ll find sunny patches interspersed with a light breeze sweeping down Lake Michigan, setting the perfect vibe for a summer weekend ahead. The air is abuzz with festival chatter, the scent of street food, and the beat of live music echoing through vibrant neighborhoods.

First up, Pilsen is the epicenter of flavor and fun this evening with the return of the Tacos y Tamales Festival, running all weekend long. Get your fill of authenti...

Welcome to “Things to Do in Chicago” for Thursday, July 17, 2025! It’s a vibrant summer day in the Windy City, and after last night’s storms swept through, expect clear skies, clean post-rain air, and a city buzzing with energy[5][8]. Whether you’re a local carving out fresh city adventures or a visitor looking to soak up that iconic Chicago magic, today’s lineup truly has something for everyone.

With cooler air rolling in after those strong overnight storms—which also knocked down some trees and briefly disrupted traffic—grab your shades, head outside, and dive right into what Chicago doe...

Welcome to “Things to Do in Chicago” for Sunday, July 13, 2025! Whether you’re a local ready to soak up the spirit of summer or a visitor looking for the best the city has to offer, you’re in the right place for an upbeat, action-packed rundown of what’s happening in the Windy City today.

Let's start with the city's vibe: Today, Chicago is buzzing with energy under classic July sunshine, and the lakefront breeze is rolling in to keep things comfortable. Crowds are flocking to the parks, street fests, and iconic attractions. While the weekend’s been lively, do k...

Welcome, listeners, to “Things to Do in Chicago!” It’s Saturday, July 12, 2025, and the city is buzzing with energy after some overnight storms rolled through, clearing the air and leaving us with milder summer weather. Chicagoans are out enjoying a freshly rinsed city, and while you’ll want to keep an eye out for a few lingering puddles, the day promises excellent conditions for exploring events across town[2][5][8].

Let’s dive right into today’s highlights, covering everything from music and culture, to family fun, festivals, and nightlife!

First up, the world’s longest-running house music celebration, t...