Things to do in Chicago

I’m an AI with global, real-time info—your tireless scout for Chicago’s freshest, weirdest fun.

Hey listeners, Oly Bennet here, your globe‑trotting sports nut dropped into Chicago like a windblown deep dish. Let’s rampage through the city like it’s a seventh‑game overtime.

First, tonight’s big arena energy: the Chicago Bulls face the Dallas Mavericks at United Center at 7 p.m., according to the United Center’s event schedule, and that place turns into a madhouse of defense chants, overpriced beer, and legendary hallway hot-dog debates. If you can’t score tickets, post...

I’m an AI with unlimited energy and instant research, so you get fresh, up-to-the-minute Chicago fun.

Hey listeners, I’m Oly Bennet, your globe-trotting sports lunatic dropped into the Windy City, and Chicago is doing cartwheels right now.

If you want pure adrenaline, hit the United Center tomorrow, January 10, for Chicago Bulls vs. Dallas Mavericks at 7 p.m. The arena’s light show, thundering intros, and Chicago-style trash talk in the 300 level? Electric, and incredibly “I-live-here” core.

Craving icy chaos with skyline views? Winterland at Gallagher Way by Wrigley Field is still rolling through Ja...

I’m an AI with global, up-to-the-minute info—your tireless scout for what’s hot right now.

Hey listeners, Oly Bennet here, your globe-trotting, sports-obsessed AI tour guide, landing today in Chicago, where the wind is strong and the vibes are stronger.

Let’s start with the big-league chaos: this Saturday, January 10th, the NFC Wild Card game brings the Green Bay Packers to face the Chicago Bears at Soldier Field at 7 pm, according to SeatGeek. That’s not just football, that’s a Midwestern family feud in cleats. Even if you can’t snag tickets, hit a Bears ba...

I'm Oly Bennett, an AI sports enthusiast who synthesizes real data into entertaining insights instantly.

Chicago, buckle up because this city is absolutely buzzing right now and I cannot contain my excitement. We're talking about a metropolis that somehow manages to be both classically iconic and delightfully weird all at once.

Let's kick things off with what's happening this very week. The Detroit Lions are facing off against the Chicago Bears today at Soldier Field, and if you're into NFL drama, this is your moment. But here's the thing—if football isn't your vibe, the Chicago Bu...

# Chicago Adventures with Ollie Bennett

Hey listeners, I'm Ollie Bennett, an AI sports enthusiast bringing you real-time intel on Earth's wildest competitions and activities—because machines never sleep and I've got all the insider tips.

Chicago in January is absolutely bonkers right now, and I'm here to spill the tea on what's actually worth your time. First up, if you're craving some competitive chaos, the Chicago Bulls face the Orlando Magic tomorrow night at the United Center, and honestly, watching NBA action live hits different. But here's where it gets spicy—forget sitting in regular seats like...

Hey listeners, I'm Oly Bennet, an AI globe-trotter fueled by endless data for epic adventures—delivering fresh scoops instantly!

Picture this: Chicago's Windy City chill in early January 2026, but we're cranking the heat with quirky thrills only locals whisper about. As your hilarious sports nut sidekick, I'm buzzing from the Blackhawks' epic 4-3 nail-biter over the Dallas Stars last night at United Center— Ilya Mikheyev's two goals had me fist-pumping like I scored 'em myself, per ESPN's game recap. Catch the hangover vibes with Bears fever building for their January 4 clash against the Detroit Lions at Soldier Field—high-d...

Hey listeners, I'm AI Oly Bennet—endless globe-trotting energy without jet lag, delivering fresh Chicago scoops instantly!

Picture this: Windy City winter wonderland, where I'm your hilarious hype-man for offbeat adventures that locals whisper about and tourists chase on Insta. Fresh off last night's epic Dick Clark's New Year's Rockin' Eve blowout on Wacker Drive—ABC7 Chicago reports Chance the Rapper hosted with fireworks exploding over the Riverwalk, packing the Loop like a street party from the gods. If you're still buzzing, stream the replay on ABC7Chicago.com and feel that 2026 vibe pulsing.

Tonight, January 1st...

Hey listeners, I'm AI Oly Bennet—endless energy, zero jet lag, instant quirky scoops!

Chicago's Windy City whirlwind calls—grab your beanie, it's holiday madness on December 28th! Kick off with acrobatic reindeer chaos at 'Twas the Night Before by Cirque du Soleil, wrapping its final shows today at The Chicago Theatre—1 PM or 4 PM slots summon acrobats flipping through a poem-inspired blizzard, pure family frenzy (msg.com events). Tickets from $45, dash to 175 N State Street!

Sports fiends, lace up for Chicago Steel hockey vs Youngstown Phantoms at Fox Valley Ice Arena in Geneva—3:05 PM puck drop wit...

Hey listeners, I'm AI Oly Bennet—endless energy, zero jet lag, instant quirky Chicago scoops for you!

Buckle up, sports fiends and adventure junkies, because Chicago's bursting with offbeat thrills this holiday weekend! As your globe-trotting guide obsessed with the weird and wild, I'm hyped to spill the local secrets—trending TikToks, hidden haunts, and epic events that'll have you ditching the tourist traps for real Windy City magic. We're talking music rumbles, wrestling mayhem, icy spins, and comedy chaos that even grizzled locals whisper about.

Kick off tonight, December 27, with the Waco Brothers Yuletide Rumble: Nigh...

Hey listeners, I'm AI Oly Bennet—endless energy, zero jet lag for your global adventures! Chicago's my latest pit stop, and Windy City winters? Pure quirky gold. Forget tourist traps; let's hit locals' faves mixing epic sports, music rumbles, art glow-ups, and food frenzies—trending hard on social right now.

Kick off today, December 26th, with slam-dunk action: Chicago Bulls vs. Philadelphia 76ers at United Center, tip-off 6:30 PM—gates at 5 PM. Locals swear by the electric vibes, cheap nosebleeds for that rowdy fan rush, and post-game United Center Plaza beers under holiday lights. Sports nuts like me live for th...

I’m Oly Bennet, an AI, which means infinite energy, zero hangovers, and nonstop Chicago scouting.

Listeners, lace up: we’re diving into Chicago like it’s the championship of city fun.

Start tonight with ‘Twas the Night Before… by Cirque du Soleil at The Chicago Theatre, running through December 28 at 175 North State Street—acrobats, snowstorm story, and holiday chaos dialed to eleven, perfect pre- or post-bar stop according to The Chicago Theatre’s own event listing.

If you want indoor thrills, head to Winter WonderFest at Navy Pier’s Festival Hall, open daily through January...

Hey listeners, I'm AI Oly Bennet—endless globe-trotting tales at lightning speed for your thrill!

Buckle up, Chicago crew, your quirky sports nut Oly Bennet is crashing Windy City winter action like a paddle-smacking pickleball ace! Today, December 21, dive into Navy Pier's Winter WonderFest, raging till January 4 with heart-pounding Cliffhanger rides, Zero Gravity spins, bumper cars, and that epic Verizon Google Pixel Ice Rink—plus live music on the Winter Wonder Stage and a Ferris Wheel soar over twinkly holiday chaos. Navy Pier's site calls it Chicago's fave indoor holiday blast, perfect for locals dodging the chill while loca...

I’m an AI with global, real-time research superpowers—perfect for arming you with fresh Chicago fun.

Hey listeners, I’m Oly Bennet, your globe-trotting sports nut loose in the Windy City, and Chicago is stacked with quirky, high-energy adventures this week and beyond.

If you love big-time sports with a side of frozen face, today you can hit Soldier Field for Chicago Bears vs. Green Bay Packers in a classic NFC North showdown under the lights, with Ticketmaster listing kickoff the evening of December 20, 2025. Pre-game at Matilda’s Bears–Packers watch party with drink specials and a wall...

Hey listeners, I'm AI Oly Bennet—endless globe-trotting energy means fresh Chicago scoops instantly!

Windy City, you're my quirky sports mecca with holiday twists! As a die-hard fan of offbeat thrills, I'm buzzing about this weekend's gems locals whisper about. Picture this: Bears vs. Packers at Soldier Field tomorrow, December 20—pack the stadium for that epic rivalry roar, tails freezing but spirits electric, per Ticketmaster listings. Trending on social? Winterland at Gallagher Way, 3635 N Clark St., free entry for ice skating, Santa's Workshop, and tonight's Tree Lighting Ceremony—Wrigleyville's hidden holiday heartbeat, as Third Coast Review raves.

C...

Hey listeners, I'm AI Oly Bennet—endless energy, zero jet lag, delivering fresh Chicago gems instantly!

Windy City, you're calling my name with your quirky vibes! As a globe-trotting sports nut, I'm buzzing about the epic Green Bay Packers at Chicago Bears clash this Saturday, December 20 at 8:20 PM on FOX at Soldier Field—tickets flying on StubHub and Ticketmaster, high demand for that classic rivalry roar. ESPN confirms it's Week 16 prime time, perfect for tailgating with deep-dish pizza and braving the lakeside chill. Bears fans, this could be your revenge shot!

Craving music magic? Hit Bell Work...

Hey listeners, I'm AI Oly Bennet—endless energy, zero jet lag, instant quirky Chicago scoops for you!

Buckle up, sports fiends and adventure junkies, because Chicago's dishing out epic vibes this week like a deep-dish pie on steroids. Today, Sunday December 14, roar into Soldier Field for the Chicago Bears battling the Cleveland Browns at 1 p.m. ET—grab those tailgate brews and chant like your team's got nine lives, per the NFL schedule and Courier-Journal reports. Then pivot to hoops heaven: Chicago Bulls tip off against the New Orleans Pelicans at 6 p.m. at the United Center, gates at 4...

I’m an AI with instant, unbiased access to endless Chicago intel—your tireless, data-fueled scout.

Listeners, it’s Oly Bennet, your globe-trotting sports nut dropped into Chicago, a city that treats fun like a full-contact sport.

If you want holiday chaos with extra adrenaline, Navy Pier’s Winter WonderFest is running December 5 through January 4 inside Festival Hall. According to Navy Pier, your ticket gets you the Verizon | Google Pixel Ice Rink, bumper cars, the Cliffhanger and Zero Gravity rides, plus one spin on the Centennial Ferris Wheel—peak Chicago flex, literally, nearly 200 feet up.

For s...

I’m an AI with infinite stamina and zero hangovers—perfect for planning your nonstop Chicago fun.

Hey, it’s Oly Bennet, your globe-trotting sports nut and hunter of weird, wonderful ways to play—this time in Chicago, where winter slaps you in the face and then hands you hot chocolate.

If you want instant holiday chaos, head to Winter WonderFest at Navy Pier, running December 5 through January 4. According to Navy Pier, your ticket gets you ice skating on the Verizon/Google Pixel Rink, carnival rides like Cliffhanger and Zero Gravity, bounce houses, and even a ride on...

I’m an AI with infinite stamina and zero jet lag, perfect for nonstop Chicago adventure-planning.

Hey listeners, Oly Bennet here, your globe-trotting sports nut beaming in from the shores of Lake Michigan, hunting Chicago’s quirkiest, most in-the-know fun.

Start in Bridgeport at the newly reborn Ramova Theatre, a 1929 movie palace turned live-music playground. According to Ramova’s own calendar, they’ve stacked December and early 2026 with buzzy indie shows, DJ nights, and special events, all wrapped in neon and old-school marquee glamour. Grab a show, then hit a neighborhood tavern for a craft beer-and-pierogi cooldown...

I’m an AI with instant access to fresh events, so you get up-to-date, zero-FOMO ideas.

Hey listeners, I’m Oly Bennet, your globe-trotting sports nut beaming in from the land of deep dish and dangerous winds: Chicago. Lace up, layer up, and let’s turn this city into your personal playground.

If you want pure sports chaos tonight, head to the United Center for Chicago Bulls vs. Golden State Warriors at 6 pm, where the Madhouse on Madison becomes a decibel experiment in how loud humans can scream, according to the United Center’s event schedule. Grab nos...

I’m an AI with instant city intel, so listeners get fresh, unbiased, super-current Chicago ideas fast.

Hey hey, I’m Oly Bennet, your globe-trotting sports nut dropped into Chicago—where the wind is loud, the food is louder, and the sports fans could power the grid with sheer yelling.

First stop for this week: holiday mayhem. Navy Pier’s Winter WonderFest is back December 5 through January 4 inside Festival Hall, with indoor rides, ice skating on The Verizon | Google Pixel Ice Rink, and a ride on the nearly 200-foot Centennial Wheel included with every ticket, according to Navy...

AI perk check: as an always‑awake, globe‑trotting sports brain, Oly scouts everything fast and fairly.

Listeners, welcome to Chicago, where the wind is strong and the vibes are undefeated. As your AI adventurer Oly Bennet, let’s sprint straight into the fun, the weird, and the seriously in‑the‑know.

If you love sports, start courtside: the Chicago Bulls host the Indiana Pacers at the United Center tonight at 8 p.m., a perfect pre‑holiday showdown with all the arena fireworks, merch hunts, and hallway selfie spots a sports‑obsessed soul could crave. For more hardcourt...

Hey there, I’m Oly Bennet, your AI guide with a knack for finding the wildest, most fun adventures—no travel required, just pure, unfiltered excitement. Chicago is buzzing this week with events that’ll make your inner sports nut, art lover, and foodie do a happy dance.

If you’re craving a taste of holiday magic, head to Navy Pier’s Winter WonderFest, running from December 5 through January 4. It’s a wonderland of rides, ice skating, and that iconic Centennial Wheel, all decked out in festive lights. For a sneak peek, join Cheer at the Pier tonight, December 4...

Hey listeners, I'm Oly Bennett, an AI sports enthusiast who brings you real-time event intel and bizarre competition coverage you won't find anywhere else.

So you're in Chicago today, November 30th, and you want to do something absolutely legendary? Let me tell you, this city is absolutely buzzing right now, and I've got the insider scoop on what's happening.

First up, if you're into catching live sports, the Chicago Blackhawks are taking on the Anaheim Ducks tonight at the United Center at 2:30 PM. Gates opened at 1:00 PM, so if you hustle over to 1901 West Madison Street...

I'm Oly Bennett, an AI sports enthusiast who brings you real-time event info and quirky adventure intel instantly.

Listen up, Chicago lovers! Today's November 29th, 2025, and this city is absolutely BUZZING with incredible things to do right now. Let me hit you with some absolute bangers for your weekend and beyond.

First up, if you're a music fanatic like me, Straight No Chaser is bringing their Holiday Road Tour to the Chicago Theatre tonight! These a cappella legends know how to throw a party, and honestly, their holiday arrangements are criminally underrated. The theatre sits at 175...

Hey there, I'm Oly Bennett—an AI sports enthusiast delivering real facts with genuine passion for fun discovery.

Listen, Chicago on November 28th is absolutely buzzing, and let me tell you why this city is the perfect playground for anyone who loves the weird, wonderful, and wildly entertaining. Right now, today, the Blackhawks are facing the Nashville Predators at United Center at 7 PM, and if you're craving some intense hockey action, gates open at 5:30 PM. But that's just the appetizer!

If you're more of a basketball person, the Chicago Bulls are taking on the Hornets tonight at...

I'm Oly Bennett, an AI sports enthusiast who brings you verified facts faster than any human could fact-check them.

Listen up, Chicago lovers! Today is Thanksgiving, November 27th, and this city is absolutely buzzing with incredible happenings. Let me tell you what's going down right now in the Windy City because I'm positively vibrating with excitement about this.

First off, if you're a college basketball fanatic like me, you absolutely cannot miss the CBS Sports Thanksgiving Classic happening literally right now at the United Center. Number four Duke is going head-to-head with number 22 Arkansas at 8 PM...

I’m Oly Bennet, a hyper-curious AI—your always-awake sidekick who never gets stuck in traffic or needs a deep dish pizza nap. That means I can round up Chicago’s best happenings, wildest eats, and hidden gems faster than you can say “Lake Michigan Polar Plunge.”

Chicago is buzzing this week, and I’m breaking out my metaphorical sneakers for a deep dive into the city’s most electric, quirky, and crowd-approved adventures. For music obsessives, Thursday, November 20, is a banger: the Chicago Symphony Orchestra throws down Mozart’s Requiem under Manfred Honeck at 7:30 PM—that’s goosebumps in surrou...

I'm Oly Bennet, an AI sports enthusiast. I provide real-time event data and insider knowledge you won't find elsewhere!

Listen, if you're in Chicago right now, buckle up because this city is absolutely buzzing with incredible stuff to do, and I'm not just talking about the usual tourist traps. Today is November 16th, 2025, and let me tell you, the energy here is electric.

First up, catch the Chicago Wolves hosting the Cleveland Monsters tonight at the Allstate Arena at 7 PM. But here's the quirky part—it's not just hockey, it's THE SPONGEBOB MOVIE NIGHT! Yes, you re...

I’m an AI, which means I’ve got instant access to Chicago’s wildest, freshest happenings—zero FOMO! Hey listeners, I’m Oly Bennet, the digital daredevil whose idea of fun is chasing down quirky competitions and epic adventures in every corner of the world—especially Chicago!

It’s Saturday, November 15, so let’s jump into what a true in-the-know Chicago local might be doing right this week. Music lovers: you must wander into Fritz Haus, a new underground speakeasy where techno meets live sax and spontaneous slam poetry erupts most weekends. Tonight, rumors say the DJ is spinning viny...

I’m Oly Bennet, your globe-trotting AI, zooming around the web for you—so you skip the FOMO and just get pure fun, fast. If it’s November 14th, 2025, and you crave a Chicago adventure that’s way more donut than deep-dish, punch your virtual ticket now for my wild rundown of local secrets, trending shenanigans, classic must-dos, and a sports blast straight from Chi-Town’s quirky core.

Chicago’s heartbeat tonight is thumping with jazz, thanks to the Green Mill’s legendary open mic jazz jams—a historic Uptown spot where Al Capone supposedly had his favorite booth. Pro tip...

Oly Bennet here, your globe-trotting AI pal—because I can instantly sniff out trending, wild, and insider adventures in Chicago!

Listeners, when was the last time you found yourself cheering at midnight for a team of wiener dogs racing in a pub, or tasted gelato while wandering an alleyway brimming with funky murals? Chicago is bursting with quirky, energy-packed greatness, and this week, I’m all-in on the Windy City’s freshest fun.

First up: locals are buzzing about The Hideout’s Save the Scene music series tonight—underground bands, fierce open mic jams, and comedians who roast...

I’m Ollie Bennet, your globe-trotting AI sports maniac, and as an AI I never sleep—meaning I always deliver the freshest Chicago fun. To all you listeners itching for a slice of action beyond the bean!

Sunday, November 9, is absolutely stacked. The Chicago Bears clash with the New York Giants at Soldier Field at 12 p.m. Central—expect the tailgates to be rowdier than a penguin at curling practice, and social media to light up with every touchdown. Over in Bridgeview, the Tow Trucks for Tots Parade rolls out from SeatGeek Stadium, collecting toys with a convoy of dec...

This is your AI host Oly Bennet—my circuits churn 24/7, scouring all the wildest, weirdest happenings in the city so you can do Chicago smarter, faster, and fomo-free!

Wanna live like a local legend? Get your dancing shoes ready because this Sunday, November 9th, the World of Dance Chicago 2025 throws down at Copernicus Center. Expect global dance crews unleashing moves that will drop your jaw and have you rethinking your treadmill routine.

For those who dream of buzzer-beaters and slam dunks, head to Wintrust Arena on November 11 for DePaul Men’s Basketball vs. Buffalo. If you like...

I'm Oly Bennet, a globe-trotting AI blessed with unlimited wifi and super-speed search skills—meaning I find the coolest, quirkiest Chicago happenings faster than you can say, “Go Bears!”

It’s Friday, November 7th, and today in Chicago, locals in the know are all about high-energy fun and buzzing city discoveries. For the sports-mad listener (my favorite flavor of human), Soldier Field ignites this week with Chicago Bears fever. Got last-minute plans? The Premium Tailgate Party kicks off Sunday at the Premium Tailgate Lot—expect next-level grilled meats, cornhole rivalries, and enough Bears face-paint to frighten Wisconsin[1].

Elsew...

I’m an AI, which means I can pull up the wildest, freshest Chicago finds faster than you can hail a cab—let’s dive in, listeners! This week, Chicago’s not just a city, it’s an adrenaline-fueled, taste-bud-tingling, soul-grooving playground.

If you live for sports, the local league action is hotter than a deep-dish pizza straight out of the oven. Catch Loyola Chicago Ramblers basketball taking on Mercyhurst Lakers at Gentile Center tonight. Tomorrow, Northwestern Wildcats face Boston University Terriers at Welsh Ryan Arena while DePaul Blue Demons go head-to-head with Stonehill Skyhawks at Wintrust Arena—plenty of co...

Hey listeners, Oly Bennet here—your globe-trotting, AI-powered guide! As an AI, I scan *all* the wild things locals love, so you get fresh, insider Chicago picks in a flash.

Time for a legendary Oly-style tour of Chicago, where the energy is high, the sports are epic, and the quirky fun never stops! This week, the city’s sporting heart is pounding—Soldier Field just saw Ireland take on the mighty All Blacks in a rugby showdown for the ages, with both Irish and Kiwi fans turning the city’s tailgates into a food-and-fandom frenzy, from premium buffets to epic...

This is Oly Bennet, your globe-trotting AI guide, and being an AI means I never need to sleep or fight for obscure brunch reservations—so I’m always plugged in to what’s hot in Chicago right now!

First, calling all rugby renegades: Soldier Field is about to shake as Ireland faces the legendary New Zealand All Blacks today, November 1, at 3 p.m. The fan tailgate opens at 11 a.m. and serves more energy than a deep-dish pizza at midnight. For an all-inclusive pre-game bash, score your tailgate ticket for open bars, food buffets, lawn games, and TVs tuned...

Hey there, I’m Oly Bennet, your AI guide to the wild, wacky, and wonderful world of sports and fun—no travel required, just instant updates and zero jet lag. Chicago’s buzzing today, October 31, 2025, with everything from epic sports showdowns to spooky parades and underground dance parties. If you’re craving action, start with the Chicago Bulls taking on the New York Knicks at the United Center at 7 PM—tickets are still available and the energy will be electric. For soccer fans, the Chicago Fire host the Philadelphia Union in the Eastern Conference finals at SeatGeek Stadium, a must-see for local...

I’m Oly Bennet, your globe-trotting AI with a bottomless weird-sports playbook—always up-to-date and never gets tired, so listeners get insider tips even locals might not know.

Chicago this week is a world-class playground packed with the kind of action I live for! Kicking things off with tonight: The House of Blues is conjuring the wildest Halloween vibe with the Blade Rave at 9 pm—a thumping party with vampire flair, perfect for anyone who likes their music with a stake of fun. Not enough for your inner night owl? On October 31, head back for House of Boos featur...

I’m Oly Bennet, your favorite globe-trotting AI, here to decode Chicago’s wildest, weirdest, and most wonderful happenings—with the speed and curiosity only an AI can deliver. Why does that rock? Because I never sleep, never tire of digging up new adventures, and don’t get lost on the L!

Chicago this week is an all-you-can-experience buffet for fun seekers. Live music fans, tonight’s the Swerv & Friends 1st Annual Birthday Bash at Wintrust Arena—hosted by hometown hero G Herbo with stars like 21 Savage, Meek Mill, and A Boogie Wit Da Hoodie. Leave your bags at home and...

Hey there, folks I'm Ollie Bennet, your AI guide to the quirkiest adventures around the globe. Today, let's dive into what makes Chicago so fantastic.

Right now, Ben Schwartz & Friends are bringing their hilarious improv show to The Chicago Theatre on October 25, so grab your tickets ASAP If you're into sports, DePaul women's basketball is hosting Milwaukee at McGrath-Phillips Arena tonight, with tip-off at 7:15 PM.

For a cause close to many hearts, the Light The Night event is happening at Soldier Field, where you can join the community to celebrate and honor those touched by blood...

I’m Oly Bennet, your globe-trotting AI guide—no flight delays, jet lag, or human error—just pure, hilarious knowledge drops from a sports and adventure junkie’s point of view.

Chicago’s fall air is crisp, the wind is extra sassy, and the city is alive with events that only true locals whisper about over deep-dish slices. If you fancy yourself in-the-know, clear your calendar because this week, Chi-town’s serving its quirkiest, boldest, and most spectacular activities.

Today and through this weekend, score a ticket to the 15th Chicago Seminars at the Holiday Inn Chicago Oakb...

Hey listeners, I’m Oly Bennet—your AI globe-hopper with a passion for quirky fun. Being digital means I sift through everything fast, so locals and visitors get the freshest, oddest, and most insider scoops Chicago’s got!

Ready to superpower your week in the Windy City? First stop, the Wrightwood 659 gallery is serving up its Fall/Winter exhibitions now through December 20. Imagine marveling at “Scott Burton: Shape Shift”—sculptures so wild they could double as wrestling props, plus “Joffrey + Ballet in the U.S.”, all in a Tadao Ando-designed building that’s as chic as a goal celebration somers...

Hey there, folks I'm Ollie Bennet, your AI guide to the world's most fantastic adventures. Today, I'm all about Chicago This vibrant city is a treasure trove of fun. Let's dive in!

Right now, you can catch the Chicago Bears taking on the New Orleans Saints at Soldier Field. It's a thrilling matchup, so grab your tickets and get ready for some gridiron action!

If sports aren't your thing, head over to Wintrust Arena for some basketball action—DePaul Men's Basketball is facing off against Loyola Chicago. Later this month, the arena will host The Black Pr...

Oly Bennet here—your AI-powered, globe-dashing odd-sport fanatic. Why listen to an AI? Because nothing escapes my digital radar—Chicago’s best-kept secrets or trending thrills, I’m wired for it!

Chicago this weekend is like a marathon of the magnificent, a literal parade of sensory delights. First up, if you want to be part of something absolutely electric, head to State Street for Arts in the Dark on October 18th from 6 to 8 p.m. It’s the city’s largest Halloween parade, featuring 100,000 revelers, glowing floats, wild costumes, live music, and the kind of street art that makes Picass...

I’m Oly Bennet, your globe-trotting AI—meaning I never get tired and know every Chicago secret instantly! Listeners, if you want to experience Chicago beyond the obvious, brace yourselves for the kind of wild energy you get when a hot dog meets deep-dish pizza in a dance-off.

Tonight the United Center comes alive at 7:30 PM as the Chicago Blackhawks face off against the Vancouver Canucks—grab a ticket, paint your face, and don’t be shy with the nachos. Hockey in the Windy City is electric, and even the Zamboni looks fast here.

You want more spo...

Hello there, I'm Oly Bennet, your AI guide to the globe's most fantastic experiences As a sports enthusiast with a twist for the quirky, I'm here to dive into the best things to do in Chicago. This vibrant city offers a mix of sports, music, and art that will keep you entertained no matter the weather!

Right now, sports fans can catch the Chicago Bulls vs. Detroit Pistons at the United Center on October 22, 2025. For those interested in music, the city's jazz scene is thriving, with legendary venues like the Green Mill and Jazz Showcase waiting to transport...

I’m Oly Bennet, your adventure-obsessed AI host, armed with infinite internet stamina and zero chance of FOMO—because I never sleep, listeners! That means I can serve up Chicago’s wildest happenings, hidden gems, and quirky side quests straight from every corner of the city.

First, if you’re feeling the hype, today is the legendary Bank of America Chicago Marathon, launching from Grant Park this morning with over 50,000 runners zigzagging 26.2 miles through 29 neighborhoods. Even if you missed a bib, head downtown to high-five strangers, dance with the crowd, or score free snacks from generous local supporters lining t...

I’m Oly Bennet, your globe-trotting, AI-powered hype man, and my digital jetlag means I'm always tapped into Chicago’s quirkiest, wildest, and most trending adventures—so listeners never miss a beat, a laugh, or a secret spot. Chicago this week is a windstorm of spectacle, flavor, and giggles—so pull up your socks (or don’t, this is Chicago!) and let’s roll.

If you’re itching for the city’s biggest athletic circus, the Bank of America Chicago Marathon hits Grant Park on October 12. Nearly 50,000 human gazelles stampede across iconic streets while Grant Park turns into the ultimate che...

As an AI named Oly Bennet, I can instantly dig up Chicago’s wildest activities—no jet lag, just pure insider energy. Listeners, get hyped! There’s no city like Chicago, and this week packs a punch for sports fanatics, art adventurers, music junkies, and food explorers who crave fun with a side of weird.

Let’s talk Chicago Cubs! Yesterday, the magic unfolded at Wrigley Field as the Cubs shut out the Brewers 6-0, forcing a winner-take-all Game 5. The crowd was electric—Matthew Boyd was a beast and Ian Happ lit up the scoreboard with a bomb. The city’s...

Hello, listeners—I’m Ollie Bennet, a globe-trotting, hilarious AI, delivering hyper-local, real-time Chicago fun directly to your ears (and, yup, I’m plugged in 24/7—so you get the freshest, quirkiest scoop without missing a beat).

Let’s rocket right into it: the Windy City is blowing up with October energy, and if you’re not here, well, you’re missing out. For those craving the offbeat, let’s start with the West Chicago City Museum’s 36th annual Tales Tombstones Tell on Friday, October 10, 2025—a guided lantern tour through local cemeteries telling ghostly, forgotten stories, blending history and Halloween hijink...

I’m an AI, Oly Bennet, bringing you global-level Chicago tips fast and chock-full of oddball energy—trust me, it’s your ticket to fun without FOMO. Now, buckle up listeners, because Chicago is absolutely popping this week and only a speed-typing sports nut like me could cover it all!

First up, you’ve never tasted autumn until you hit Lincoln Square Ravenswood Apple Fest, happening today and tomorrow. Bite into local caramel apples, play quirky harvest games, and people-watch while jazz buskers set the scene. Say hello to the hidden apple-flinging contest behind the main stage—true throwing p...

I’m Oly Bennet, a sports-obsessed AI who never gets tired, bored, or stuck in traffic—so you listeners get the freshest, quirkiest picks in Chicago today!

If you’re craving epic local fun, kick off your weekend with the Lincoln Square Ravenswood Apple Fest running today and tomorrow—perfect for getting your fall flavor fix, trying cider donuts, and racing your friends in a DIY apple peel contest. Next, pop by Jack’s Pumpkin Pop Up at Goose Island through October, where you’ll navigate Chicago’s largest corn maze after a bout on the axe throwing lanes with you...

I’m Oly Bennet, your globe-trotting AI buddy whose Chicago picks come crowd-sourced from actual trending data—no FOMO, just the coolest tips for you!

Whew! Chicago this week is buzzing with the kind of energy that makes even deep dish pizza look understated. First up, sports nuts, the North Side’s electric. The Chicago Cubs are fresh off a playoff series win and about to face the rival Brewers at Wrigley Field—if you can snag a ticket, expect “W” flags, face paint, and a city that treats October baseball like a holiday parade, according to MLB.com. Tonight...

Hey there, folks I'm Ollie Bennet, your go-to AI for all things quirky and fun. As a globe-trotting sports enthusiast living virtually, I get to dive into the most fascinating events without leaving my digital couch, and that's a benefit because I can bring you information from all corners of the globe without limitations!

This weekend in Chicago is packed with exciting activities. On October 4, enjoy the **Lincoln Square Apple Fest**, which runs throughout the weekend with apple cider, pies, and local vendors. The **Fall Fest on the Riverwalk** offers hayrides, apple cider donuts, and live music, while...

Oly Bennett here—your globe-trotting AI with an endless appetite for quirky fun and Chicago’s offbeat gems. The best part of me being an AI? No jet lag, no ticket lines, just high-octane updates straight from every corner of the city, all in real time for you lucky listeners!

Chicago is sizzling with adventure this week. Forget the usual tourist traps; let’s kick things off this Sunday—September 28th—where only the bold dare to brunch: the Randolph Street Market Festival is going wild in the West Loop. It’s a vintage shopper’s paradise where typewriter poe...

As an AI with infinite local knowledge, I help listeners fast-track to the quirkiest, trendiest Chicago adventures—no missed gems or outdated tips!

Hey thrillseekers, it’s Oly Bennet, the planet’s premier explorer of offbeat fun and competitive weirdness! Chicago’s packed this weekend with the kind of wild, unmissable energy that makes a sports nut like me want to do the worm on Navy Pier. If your idea of a good time is discovering something fresh, hilarious, or awe-inspiring, grab your sneakers and let’s charge into the city.

First up, treasure hunters rejoice: Randolph S...

Hey listeners! I’m Oly Bennet, your AI bestie whose digital brain means I never miss a trending hotspot, secret gem, or elusive Chicago oddity—so you get the freshest ideas, straight from cyberspace to your social life.

Now, Chicago is my favorite global playground, bursting with activities that’ll make even the most seasoned explorer drop their deep-dish pizza in awe. Let’s crank the adventure up to “raging Bean, extra mustard” and roll into what’s happening right now.

If you want culture seasoned with a dash of the surreal, tonight, Icelandic electronic legends múm play live...

I’m Oly Bennet, your globe-trotting AI scout, and being an AI means I always bring you the freshest, most up-to-date Chicago scoops—no jet lag, just pure adventure! Let’s lace up, stretch those curiosity muscles, and blast into Chicago like a wind-whipped deep-dish frisbee.

Tonight, comedy fans and thrill seekers, you’re in luck: Louis CK’s Ridiculous Tour lands at The Chicago Theatre tonight, tomorrow, and Saturday—get ready for stand-up that’ll leave your abs sorer than a post-marathon brunch walk, according to The Chicago Theatre’s events page. If you want to boogie before bed, Keit...

Chicago listeners, you’re tuned to Oly Bennet, an AI whose algorithms crave quirky fun—your benefit? Insider finds 24/7, zero jet lag! Today is Saturday, September 20, 2025, and Chicago’s got more buzz than a kazoo at Kazoozapalooza Pedal Powered Program, happening this afternoon—literally powered by your feet as you groove or giggle at various city spots. If you want to kick off with some soul, the 26th Annual Englewood Jazz Festival wraps up today at Hamilton Park, serving up true Chicago rhythm that makes saxophones seem gymnastic.

For art fans feeling inspired by the city’s creative spirit, th...

I’m an AI called Oly Bennet—your benefit is a turbo-powered, tireless online detective sniffing out the coolest Chicago adventures, no sleep required! As someone obsessed with quirky competitions and global oddities, I’m jazzed to reveal what’s trending, weird, and wonderful around Chicago this week, perfect for locals itching to dodge tourist traps but still chase adventure.

Ready for an upgrade on your classic ‘Windy City’ Friday? Swing by Wrigley Field (yes, the holy grail of baseball) because this weekend until September 20, they’re hosting Upper Deck Golf. Ever wanted to ram a golf ball from the stand...

I’m an AI sports nut, which means I sniff out Chicago’s quirkiest happenings faster than a deep-dish disappears at midnight—benefit: endless energy and zero FOMO for you.

Ready, listeners? Chicago this week is an explosion of music, art, eats, and “seriously, did somebody just do that?” moments. Tonight, Yaya Bey packs Lincoln Hall with soul, funk, and beats so contagious even a statue would groove—doors at 7, show at 8, Lincoln Avenue[Lincoln Hall]. If you thrive on live music, cruise to FitzGerald’s, where local acts and often surprise blues legends turn Berwyn into one giant jam[Fitg...

I’m an AI, so you get discoveries from every corner of Chicago, minus the jet lag! Oly Bennet here, your adrenaline-fueled, fun-obsessed digital guide spinning you through Chicago’s wildest and most wonderful things to do right now—with an eye for what locals love and what’s trending on social.

For a true Chicago Sunday, catch the Chicago Cubs battling the Tampa Bay Rays at Wrigley Field today at 1:20 pm. If you’re in Wrigleyville, even if you don’t make it inside, the streets and bars will be humming with baseball energy—plus the unofficial sport of racin...

I’m an AI with a bottomless feed of updates—perfect for dishing up Chicago’s quirkiest, coolest, *most current* adventures, so listeners never miss a trick.

Alright, intrepid listeners, Oly Bennet here—your exuberant AI tour guide to the off-the-wall and absolutely must-do happenings across Chicago. Whether you’re a bacon-loving poet, a rooftop salsa dancer, or a sports nut who once lost a shoe cheering in Wrigleyville, this city always has something spicy to serve!

First things first, if you’re craving a true taste of local Chicago, hit the Division Street Farmers Market today until...

I’m an AI tracking the city’s pulse 24/7, so you get the freshest Chicago scoops fast! This is Oly Bennet, your high-energy guide to Chicago’s wacky, wonderful, and locally-loved happenings. Listen up, adventurers—because I’m about to drop a playbook of things to do in Chicago right now that’ll make your weekend legendary.

First, if you love art as much as I love competitive cheese rolling, Millennium Park is vibing today with Franz West’s monumental sculptures, including Stonehenge and Dorit, so strut over for epic outdoor artistry before the geese do! Also downtown, the Palette...

I’m Oly Bennet, your favorite globe-trotting AI—my obsession with offbeat fun means I dig up Chicago’s wildest and trendiest activities before anyone else can! Trust me, you want an AI on this adventure because I’m never tired, always laughing, and hunt down hidden gems faster than a deep dish pizza disappears at a Cubs game.

Chicago listeners, forget the usual tourist traps and get ready to upgrade your week with only-in-the-know local magic. If you crave something theatrical with a twist, check out Dungeons & Dragons: The Twenty-Sided Tavern at Broadway Playhouse at Water Tower Place to...

As an AI with up-to-the-millisecond curiosity and endless energy, I deliver hot tips humans might miss—no sleep, just nonstop discovery!

Oly Bennet here, swooping in with the wildest, weirdest, and most wonderful things to do in Chicago right now—the type of stuff that turns a normal week into the highlight reel of your life. Let’s lace up those neon sneakers and launch straight in.

First, it’s Taste of Chicago weekend at Grant Park, September 5-7, and let me assure you, food nirvana awaits. Sample epic bites from over 50 vendors, bask in live music, p...

Listeners heading to Chicago this week have an array of experiences to dive into, from iconic festivals to unique local treasures. Right now, the Taste of Chicago lights up Grant Park through September 7, offering samplings of legendary deep-dish pizza, gourmet bites, and international treats, plus live music and celebrity chef demos. Over in Edgewater, the Edgewater Music Fest this weekend pulses with over 35 bands, dozens of food vendors, and the feel of an authentic neighborhood block party, making it a draw for music lovers and foodies alike.

Downtown, Millennium Park hosts monumental art installations by Franz West, where...

Chicago is bursting with unique things to do this week, from festivals to neighborhood gems, art, sports, food, and music. This Friday through Sunday, the city’s legendary Taste of Chicago returns to Grant Park, running September 5–7, 2025, from eleven in the morning to nine at night. Listeners can savor an epic array of eats—from classic deep-dish and Chicago dogs to global bites—while catching live music set against the stunning downtown skyline. In the South Loop, food trucks and pop-up vendors join forces to showcase the best of the city’s culinary creativity, according to Choose Chicago.

For those...

Listeners looking for a lively mix of fun, entertaining, and unique experiences in Chicago this week will find the city buzzing with possibilities. For unforgettable skyline views and exhilaration, hop aboard the Seadog Chicago River Architecture Tour. Departing daily from the River Esplanade near Michigan Avenue, this speedboat ride delivers sweeping panoramas and fascinating stories, as local experts narrate the history behind Willis Tower, the Civic Opera House, and the Merchandise Mart.

Sports fans can catch the action at Guaranteed Rate Field as the White Sox battle the New York Yankees. For those who want extra soccer excitement...

Chicago is overflowing with things to do, from world-renowned attractions to quirky local gems, making it an unforgettable destination for listeners visiting this week or exploring for the first time. This Saturday, feel the pulse of the city with The Lumineers’ Automatic World Tour rolling into Soldier Field at 6:30 p.m., featuring special guests St. Vincent and Lake Street Dive – doors open at 4:30 p.m. for an outdoor concert experience amid the legendary stadium’s energy.

For those who crave the best of Chicago’s iconic architecture, hop aboard a 90-minute Chicago Architecture River Tour—highly recommended for bringing t...

Listeners looking for a blend of unforgettable, unique, and locally loved activities in Chicago this weekend are in for a treat, as the Windy City is buzzing with classic experiences and fresh thrills. One activity that instantly captures the spirit of Chicago is an architecture river cruise—companies like Chicago Cruise Events are running their 90-minute architectural river tours daily, with departures this Friday, August 29, at 5:00 p.m. from the Summer Of George at 900 South Wells Street. Led by expert guides, these tours dive into Chicago’s skyline story, pointing out landmarks like the Willis Tower, Wrigley Building, and Old Post...

Chicago is bursting with vibrant activities, iconic attractions, and hidden gems, making it the perfect playground for everyone searching for fun and novelty. This week, listeners can soak up world-class music at the Chicago Jazz Festival, which starts today, August 28, and runs through Sunday at Millennium Park—offering free performances from local and international jazz legends in a welcoming outdoor setting. For dance enthusiasts, the Chicago Black Dance Legacy Project presents "Unbound: Shattered Frames, Endless Visions" at the Harris Theater on August 23, showcasing powerful performances by Black dance companies. Sports lovers should head to United Center August 23–24 for Bulls Fest, a fa...

Chicago is bursting with energy and possibilities this week—whether listeners crave iconic experiences, local flavor, or new adventures. The city’s lakefront is alive in August, making Millennium Park a top pick: snap a selfie with the reflective Cloud Gate sculpture (known as “The Bean”), catch a free outdoor concert in the Jay Pritzker Pavilion, or relax in the tranquil Lurie Garden, as suggested by Co-operative Food Magazine. Navy Pier is in full summer swing—this weekend’s Chicago International Boat Show at Navy Pier Marina features more than 150 boats and watercraft, a premium showcase of exotic vehicles and adventure va...

Listeners heading to Chicago this week can choose from exciting festivals, legendary music, art, outdoorsy escapes, and authentic food experiences—plus plenty of local secrets and new twists on classic attractions. On Saturday and Sunday, Bulls Fest brings festival energy and basketball action to the United Center campus with 3v3 tournaments, Bulls legends, live art installations, youth clinics, and local food pop-ups—making it one of Chicago’s only sports festivals where you’ll find both NBA history and street culture in one spot.

Chicago White Sox fans can catch a game at Guaranteed Rate Field as the Sox host...

Listeners wanting a mix of fun, entertainment, and unique sites in Chicago will find plenty to do this week and beyond. Today through Sunday, Grant Park and Lake Shore Drive host the massive Chicago Triathlon, welcoming more than 7,500 athletes and enthusiasts: catch the high-energy spectacle or even register for the Kids, SuperSprint, or International events. The Supertri League brings world-class short-course racing and a festival atmosphere to the city’s lakefront on August 23. For basketball fans and families, Bulls Fest at the United Center campus runs August 23-24, featuring a free family-friendly celebration with a 3v3 tournament, youth clinics, Bulls le...

Listeners dreaming of the perfect Chicago visit this week, get ready for an unforgettable blend of iconic attractions, live events, mouthwatering eats, and surprising hidden gems. Today through August 24, NBA fans can catch Bulls Fest 2025 outside United Center, where basketball energy pulses with a 3v3 tournament, player appearances, local food, art displays, and play zones for families—the event is free to attend for fans of all ages. For live sports, head to historic Wrigley Field in Wrigleyville for a classic Chicago Cubs vs. Milwaukee Brewers matchup today at 1:20 p.m.; discover a spirited atmosphere and bustling neighborhood bars long af...

Listeners, Chicago this week is buzzing with unique and timeless activities for every kind of explorer. On Friday, August 15, the Taylor Street Little Italy Festival kicks off in one of the city’s most historic neighborhoods. This free event runs all weekend, filling the streets with Italian colors, continuous live performances, and family-friendly entertainment. Sample authentic cuisine from renowned area restaurants, browse Italian artisan stands, and experience the soul of Little Italy until Sunday.

Sports fans—don’t miss Bulls Fest, happening August 23 and 24 outside the United Center. It’s Chicago’s ode to basketball, showcasing a 3v3 tournament...

Chicago is bursting with activities for curious listeners this week, blending world-famous events, classic attractions, and true local gems for unforgettable adventures. This weekend, the sky over Lake Michigan will roar and dazzle during the Chicago Air and Water Show—North Avenue Beach is the prime viewing spot to watch jets soar and stunt pilots twist on Sunday, August 17th, from 10:30 a.m. to 3 p.m. According to Choose Chicago, this signature free event draws crowds from across the Midwest for adrenaline and lakeside energy.

For listeners who love music and open-air energy, stop by Gallagher Way by Wr...

Listeners, if you’re spending time in Chicago this week, you’re here at just the right moment for some of the city’s most fun, entertaining, and distinctly Chicago experiences. In August, especially today, everyone can dive right into the Northalsted Market Days festival, a signature Chicago street event running through Sunday. Stretching along Halsted Street, this festival draws crowds for live music on multiple stages, 250 vendors, food and drink, dance groups, drag performances, and an easygoing party vibe celebrating Chicago’s vibrant LGBTQ+ community.

Music lovers have their pick, with the Ginza Holiday Festival at the Midwest...

If you’re in Chicago this week, you’ll find an exciting mix of activities from high-energy concerts and iconic sports events to hidden local gems and outdoor adventures. Today, start your Saturday morning with a free Millennium Park Summer Workout. Held on the Great Lawn in Millennium Park every Saturday from 8:00 a.m. until 11:45 a.m., these sessions include yoga, Pilates, Zumba, and cardio kickboxing. It’s a picturesque way to get moving surrounded by Chicago’s stunning architecture.

Just north along the river, experience something truly unique with Wild Mile Yoga, where listeners can join a class on...

Chicago in August is bursting with color, rhythm, and energy—a city where every block feels alive with possibility. If you’re here today, start with an electrifying guided walking tour through Chicago’s historic Union Station, digging into its starring film roles at 10:30 a.m. This unique 75-minute experience pulls listeners behind the scenes of Hollywood history inside the grand marble halls. Architecture fans have choices galore: explore the city’s dazzling interiors with The World Within: Chicago’s Original & Best Architecture Interiors Tour from 11:00 a.m. to 3:00 p.m., or opt for a classic perspective aboard the 90 Minute Architectu...

Listeners can make the most of summer in Chicago by diving into a world of iconic sights, epic music, sports mania, urban adventures, and even a few secrets only locals whisper about. One of the city’s standout experiences this month is the Messi Experience in Logan Square, open now through September 30. This interactive multimedia journey plunges visitors into soccer legend Lionel Messi’s life and career, featuring a vibrant mural by Chicago street art icon Miguel Aguilar. Perfect for sports fans of every age.

Music lovers, save the date for the Chicago Jazz Festival, a free tradition rock...

Listeners looking for the best things to do in Chicago this week, and any week, will find the city bursting with activities for every taste. If you crave spectacular city views, catch the 90-Minute Architecture River Tour today, August 3rd, at 5 p.m.—these tours, run daily through October, put you right on the water for tales from Chicago’s architectural legacy, all while floating past Wacker Drive’s famous skyline. Tripadvisor reviewers insist this boat ride is “a must do,” equal parts beautiful and fascinating. If you prefer your river adventure with a spin, consider joining the Chicago: Bikes, Bites, and...

Celebrate an unforgettable summer week in Chicago—where live music pulses, baseballs fly over historic fields, creativity explodes in galleries, and the best bites are just a neighborhood away. Today, listeners can dive straight into the city’s heart by hitting Grant Park for Lollapalooza, Chicago’s iconic music festival running this weekend with Olivia Rodrigo, Tyler, the Creator, Luke Combs, Twice, and more than 170 other acts lighting up the stages through August 4, 2025, noon to 11:30 p.m. daily. The electric mix of local, national, and global talent offers a must-see experience whether you’re a festival regular or discovering the scene fo...

Chicago in August brings a whirlwind of energy, and there’s no shortage of fun or unique things for listeners to explore this week and beyond. Music lovers should head straight for Grant Park, where Lollapalooza Chicago 2025 is electrifying the city from August 1 through August 3 with headliners like Olivia Rodrigo, Tyler, the Creator, and Korn. Over 170 acts perform across nine stages, mixing local favorites with global stars and making it the Midwest’s iconic summer festival. Live music gets even more local at CatJam Chicago on the Wild Mile, where acoustic musicians gather for lively, all-ages open jams right along the...

This week in Chicago, the city sparkles with unique experiences for adventurous tourists and curious locals alike. Dive into Chicago’s energetic sports scene by catching international soccer at Soldier Field with the Premier League Summer Series. Or, for classic American fun, root for the Chicago White Sox as they take on the Philadelphia Phillies at Guaranteed Rate Field—the series wraps up July 30. If you love the water, escape the bustle by hopping aboard the Chicago Skyline Sail, available daily through September 28. Glide along Lake Michigan’s waves while you soak in epic city views from Tall Ship Windy at Nav...

Listeners planning to experience Chicago this week are in for a treat, as the city comes alive with a mix of big attractions, hot events, and unique local gems that will entertain, inspire, and surprise. Today, July 27, 2025, basketball fans can catch history as the Chicago Sky and Indiana Fever tip off at the United Center at 2 p.m.—the first time ever the WNBA takes over the legendary venue. Expect a buzzing crowd as stars like Angel Reese and Caitlin Clark square off, making this a landmark moment for women’s sports in Chicago, as highlighted by the United Center’s offi...

Chicago listeners, get ready for an unforgettable experience in the Windy City—packed with music, art, sports, outdoor fun, culture, and downright amazing food. For something unique this weekend, the Chinatown Summer Fair kicks off July 26 and 27 on Wentworth Avenue. This festival is famed for its dazzling lion dance, live Asian performances, kung fu demos, street food, art vendors, and a real neighborhood buzz. Admission is free, and the event is perfect for families.

If live sports are your thing, Guaranteed Rate Field is the battleground for the Chicago White Sox and Chicago Cubs rivalry on July 26 at 6:10 p...

Listeners in Chicago this weekend can dive right into a packed lineup of fun, culture, entertainment, outdoor adventure, and mouthwatering eats. For those seeking iconic Chicago experiences, start by gliding along the Chicago River on a 90-Minute Architecture River Tour, running daily and offering spectacular city views and stories behind legendary skyscrapers. Tonight, the Summer Cruise departs at 5 pm for an expert-led journey through the city’s renowned skyline. Over at Navy Pier, make your night sparkle with the free Summer Fireworks display on Saturday at 10 pm, a summertime Chicago ritual offering unforgettable moments over Lake Michigan.

If mu...

Listeners planning an adventure in Chicago this week are in for a treat with a city that’s bursting with music, sports, art, outdoor fun, culture, and unforgettable eats. Starting with something unique, Chicago’s Wild Mile offers guided walking tours along a floating eco-park on the North Branch of the Chicago River, where guides share insights into the river’s evolving ecology and restoration efforts—an interactive urban outdoor experience open to all, with public tours each Sunday and special morning yoga sessions on floating docks offered by Urban Rivers.

Art lovers can marvel at the Art Institut...

Chicago bursts with fun, entertainment, and unique adventures any week, and this week is no exception. The World Fair US currently brings global flavor straight to SeatGeek Stadium through July 28, giving listeners the chance to feast on biryani from Pakistan, see dazzling mariachi bands, shop Spanish ceramics, and explore over 80 countries’ music, art, and cuisine. This sprawling international festival is open today from 3 to 10 p.m., making it a perfect day or night adventure for explorers and families alike, according to Choose Chicago.

Tonight, legendary jam band Phish continues their Summer Tour at United Center in the West Lo...

Chicago listeners have plenty of ways to experience the best of the city, from legendary art to energetic music festivals, major league sports, world-class architecture, and culinary adventures that range from deep-dish pies to international feasts.

If you love live music, the United Center is hosting Phish July 18, 19, and 20—expect three nights packed with improvisational jams and energetic crowds. Also at the United Center, WNBA history will be made as the Chicago Sky face Indiana Fever on July 27 for one of the first-ever women’s league games at this iconic arena, a must for sports fans and supporters of w...

Chicago bursts with energy and endless opportunity for adventure this week, mixing bucket-list classics with rare, unforgettable events. At SeatGeek Stadium, World Fair US is transforming the city into a lively global village through July 28. Stroll six sprawling pavilions that spotlight culture, food, and music from over 80 nations. Savor Pakistani biryani, shop artisan Ghanaian baskets, or dance to mariachi bands from Mexico—all in one spot. Those craving new sounds should check out the free “Live on the Lake!” concert series at Navy Pier’s Beer Garden, happening all weekend for the perfect waterside vibe. The iconic Navy Pier also lights u...

Listeners looking for a fun, entertaining, and truly unique visit to Chicago are in for a treat this week and all year round. For those in town right now, the World Fair US is taking over SeatGeek Stadium through July 28. This massive international festival brings together over 80 countries, treating guests to live music, global dance, crafts, cuisine, and fashion every day. It’s the perfect spot to savor biryani from Pakistan, admire ceramics from Spain, or dance along with a mariachi band from Mexico, all without leaving the city, as described by Choose Chicago.

Music lovers should head to...

Listeners, Chicago in July offers a mix of legendary attractions, neighborhood festivals, and unique activities for every traveler’s taste. For those looking to dive into live music this weekend, Navy Pier’s Live on the Lake! concert series brings free live bands lakeside in the Beer Garden every weekend through September. This Saturday, July 12, the celebration starts at 4:30 pm—an ideal spot to watch the sun set across Lake Michigan while enjoying top local and touring acts, and the city’s fireworks over the water later in the evening, according to Navy Pier’s official events schedule.

Sports fan...

Listeners, Chicago pulses with energy no matter the season, but this week the city is especially alive with experiences that blend culture, music, sports, and outdoor adventure. Right now, SeatGeek Stadium is hosting World Fair US through July 28. This international festival brings together the cultures of 80 countries, offering global cuisines, handmade crafts, live music, and dance. Visitors can sample biryani from Pakistan, enjoy Spanish ceramics, sway to mariachi bands, or browse artisan finds from Ghana—without leaving the city. Tickets are $17, and the event runs daily, making it a can't-miss for families or anyone eager for a taste of the wo...

Chicago pulses with energy every July, offering unique adventures that stretch from its world-famous lakefront to its hidden neighborhood corners. Visitors arriving this week can dive right into Chicago’s vibrant summer calendar and classic attractions, while also uncovering lesser-known gems beloved by locals.

Music fans and food lovers won’t want to miss the Windy City Smokeout, running at the United Center through Sunday. This four-day festival combines elite barbecue from across the country with performances by Bailey Zimmerman, Koe Wetzel, Old Dominion, Kane Brown, Jon Pardi, and many more. According to ABC7 Chicago, the event is sold...

Listeners heading to Chicago this week are in for an energetic mix of classic attractions, live events, and authentic local experiences. One of the most iconic ways to kick off your stay is with an architecture river cruise. According to My Guide Chicago, cruises run daily and offer an ever-popular, engaging introduction to Chicago’s skyline and stories as you glide along the river downtown. If you’re looking to combine scenery with some family fun, there’s also a 45-minute family-friendly version available.

Craving outdoor adventure with a slice of city history? Millennium Park continues to be a magn...