Chicago Shows - The Second City

Caught in the one second between life and death, a man must reconcile his life choices while navigating the ridiculous characters in his head including a Shakespearean Baseball Coach, a disgruntled Buca di Beppo server, and an acid-induced gargoyle.

Frankly, My Frank blends characters and storytelling for an evening of humor and heart.

Written and Performed by Second City Alumnus Frank Caeti
(MADtv, Modern Family, Upright Citizens Brigade, Jimmy Kimmel Live)
www.frankcaeti.com

Directed by Second City etc and Mainstage Alumnus Ithamar Enriquez

Press Reviews
“Frank’s characters are as sublime as they are joyfully ridiculous and his unwavering commitment to them truly makes them burn bright”. – The Comedy Bureau LA

“It brought tears to my eyes from being both belly-achingly funny and earth-shatteringly truthful. Frank Caeti plays multiple facets of himself with ease, shifting into fully-fledged characters in the blink of an eye and showcasing their depth and their humor to the audience’s delight. He has crafted one of the most unique one-man shows I’ve seen that will stay with me for a long time. Go see it!” – Dramaworks

Audience Reviews
“Frankly my Frank, I Don’t Give a Frank is a masterclass in solo performance. The show is simultaneously hilarious, heartfelt, insightful, impressive, and inspiring. This is not an easy task, but Frank makes it look effortless.”
Kevin McGeehan – (10-Time Moth Winner, 2019 New York Moth GrandSLAM Champion)

“Frank’s mesmeric performance is sheer proof of the unfortunate narrative that show business does not necessarily reward truly exceptional talent. A breathlessly hystericaland chokingly poignant examination of passionate aspirations and the shifting perspective of priorities. Frankly, you should give a Frank. I truly loved the show.”
– Lance Barber (The Comeback, Young Sheldon)

“Frank Caeti is a powerhouse performer. He captivates the audience from minute one and never takes his foot off the gas. And amidst all the silliness he had me crying like a baby at his honesty and vulnerability.”
– Amanda Blake Davis (Second City, Hey Day)

“A vulnerable, hilarious, wonderfully layered solo show. Frank gives a stellar performance.”
– Stephnie Weir – (Second City and MADtv alum)

“This show is fantastic! I laughed, I cried, I loved every minute of it. Frank expertly weaves deep emotion, serious questions, and joyful silliness into a dazzling tapestry of love and hope.” – Erin Z.

“Frank possesses the uncanny ability to be both hysterical and vulnerable. Structurally, the show is a masterclass in story and character, all taking place in a brief moment in time. But I left the theater really moved, reflecting upon and appreciating the nuances in my own life.” – Bryan K

“A heartwarming, hilarious, memorable show that will move you and keep you giggling all hour long.” – Monette M

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo.

Ever heard of this show “Hamilton”?

Shamilton is just like that, but (ahem) better! Expect the same level of hip hop, incredible songs, moving storytelling, stunning choreography and powerhouse singing… except made up on the spot.

The New York Times called Shamilton “One of the top 5 comedy shows to catch”.

Comedy supergroup Baby Wants Candy presents “Shamilton!”, the Hamilton-inspired hip hop improvised musical created in 2016 in LA and playing to sold out crowds all over the place, including the Kennedy Center in DC, a national touring company and weekly sold out shows in New York and LA.

Join the Shamilton cast as they improvise an epic musical based on a historical figure or celebrity of your choosing…including Genghis Khan, Kim Kardashian, Mr. Rogers, or even basketball playing superdog Air Bud. You decide!

It’s the show Lin-Manuel Miranda calls, “cease and desist!”

Baby Wants Candy is a completely improvised, full band musical! Having performed over 3,000 improvised musicals to thousands of fans from Chicago to New York to Singapore to Scotland, this group not only performs in Chicago, New York, and LA but also tours internationally, including multiple sold-out runs at the Edinburgh Fringe Festival!

BWC cast & alumni include Aidy Bryant (Saturday Night Live), Jack McBrayer (30 Rock), Peter Gwinn (Colbert Report), Thomas Middleditch (HBO’s Silicon Valley), Lauren Conlan Adams (Kimmy Schmidt), Jessica McKenna (Party Over Here), Nicole Parker (Elephaba in Wickedon Broadway) and many more. Hailed as “Critic’s Pick” from the New York Times and “Best Improv Ensemble” from the Chicago Magazine, this is one improv show you don’t want to miss!

Don’t miss Chicago’s rising comedy stars before they hit TV, plus surprise guests from Netflix and Comedy Central! Get your tickets now for an unforgettable night of laughter!

Chill AF Presents the best comedians Chicago has to offer, plus special drop-ins from prominent name comedians you’ve seen on SNL, Comedy Central, and Netflix

Chicago’s top comedians battle it out for laughs, glory, and sweet sweet points in an interactive game show, featuring a live studio audience (that’s you!) Performers go head to head in a series of hilarious challenges inspired by classic game shows like The Dating Game and The Price is Right, and current hits like Game Changer and Taskmaster. Wheel of Improv will leave your head spinning – with laughter!

Check out our Linktree

Ten Dollar Comedy is a weekly comedy showcase featuring some of Chicago’s best improv, stand-up, and sketch – all for only $10.

This show is produced and hosted each week by Top Dollar Comedy, a comedy collective that features a rotating cast who have performed all over the world together. The ensemble includes: Carly Olson, Eric Muller, Eric Pedersen, Erin Goldsmith, Jonny Nelson, Peter Corey, and Deanna Ortiz.

Technology plays a huge role in our lives, and to be honest, it’s kind of a pain. The “beyond” section at Bed, Bath, and Beyond is getting out of control. There’s iphone users trying to hunt down the green bubbled Android in the group chat. And perhaps worst of all, there are children (and adults) who are incapable of eating a meal without their iPads. So slam your laptop shut, put your phone on DND, and enjoy this sketch comedy written by us. Or maybe it’s written by AI. Who knows?!

Montessori Boy is a Brooklyn-based sketch comedy group consisting of best friends Julia Tesmond, Diego Abraham, and JT Tsuchiya. Their sketches have amassed over 11 million views across Tiktok and Instagram and have been featured in Vulture for their sketch ‘JT Does a Good Deed’. Montessori Boy’s live shows can be seen in venues all around New York, where they combine their unique blend of live sketch, filmed shorts, and heinous sensibility.

Welcome to Mount Olympus like you’ve never seen it before. Olympus Has Fallen (And It Can’t Get Up) transforms the epic tales of Greek mythology into an hour of comedy that proves even immortal beings can’t escape life’s most ridiculous moments. From Pandora’s Box to Hercules’ adventures, this show has just enough mythological accuracy to make your high school English teacher proud. So grab your thunderbolts and goblets and join us for an hour fit for the Gods.

Experience the unique and unmistakable World Premier of Randy Chances “One Night Lonely”,a 30 minute variety show made up of stories, songs, jokes, gags, and unforgettable imagery all inspired by a ‘near’ death experience and a suit made entirely–ahem–of disposable diapers! Navigating dark and light corners of the human psyche, let Randy guide you in a meditation, introduce his cousin Nigel, and take you through ‘straight conversion therapy.’ Absurd, wise, and ultimately filled with joy and laughter, this is a debut not to be missed as it travels to Edinburgh Festival Fringe 2025

Thursday, July 24, 8:30 pm

The inaugural show of The Catholic School Kids sketch group, The Catholic School Kids humorously pokes fun at a Catholic education.

Laura is back and older than ever. Join her as she looks back on her 28 years of life through stand-up comedy, music of all genres and self-deprecation.

After performing iterations of this show for the past four years, Laura is thrilled to be bringing her life back to the stage. Laura is a recent winner of Best Comedian (Non-Standup) from the Chicago Reader. She has been seen at The Annoyance, iO, The Second City, Zanies, The Laugh Factory and Lincoln Lodge. Steve Cochran also deemed her a “Comedian To Watch.”

Come see stand up comedy and live music weaved together in a way that will make you wonder, “Was that really necessary?”

The show will also feature the blessing of world famous music director, Micky York. The sassiest comedian in Chicago, Joe Nicastro opens. What more could you ask for? Probably a lot- but that doesn’t matter. Just come!

An improvised take on a hit reality-TV show that dares to ask… is love truly improvised? A cast of 10 improvisers will embark on a journey through pod dates, honeymoons, shared luxury apartments, awkward family brunches, and weddings… AKA decision day. Through audience feedback and suggestions improvisers will collaboratively build a world of unforgettable characters and messy relationship dynamics. Come witness the wildest improvised love stories that you never saw coming!

Enjoy as skill and talent unfolds before you. Professional comedians, musicians, dancers, and much more come together to dazzle and display the endless possibilities of Chicago theatre.

The comedy is side-splitting, the culture is strong, and the pleasure is all ours. On any night you might see, Ballet, Stand-Up, Mexican Folk Music, Circus acts, or even my Mom!

Our show stands in the footsteps of Bill Murray, Tina Fey, Tim Robinson, Amy Poehler, Tim Meadows and the countless rest who have trained and started right here.

The Second City does sketch shows like no other, but how do we decide which sketches to include and which not to? Is it possible, nay… probable, that the director could ever be wrong when choosing to cut a sketch? When you create a sketch, it becomes your baby. And who doesn’t love to see babies fighting? Come to the de Maat Studio Theater on Thursdays in July to see the Cut Baby Battles, where Second City alum perform their sketches that were cut from different shows to see which cut baby is the best one, for the final prize of getting to tell their director “YOU WERE WRONG! “

Chicago’s first annual Windy City Comedy Fest is proud to present a night of nonstop laughs featuring a stacked lineup of rising stars and seasoned pros from the local and national comedy scene. From sharp one-liners to outrageous stories, this is your chance to see some of the funniest stand-ups from across the country- all in one show!

Are you ready for some heist-jinks? SWIPED Improvised Thievery’s crew of comedic criminals perform a 55-minute improvised longform set that pays homage to the highs and lows of the heist genre. All we need to get started is a suggestion of what outrageously valuable thing you’d like us to steal and the heist begins. SWIPED features loving references and tropes from your favorite heist media. Before your eyes, we’ll meet our mastermind, build their crew, and see what dangerous obstacles they must overcome to walk away with the prize.

Veterans of Chicago’s best improv shows like Baby Wants Candy, Improvised Shakespeare Company, Hitch Cocktails and more bring you an hour of hilarious long form improv. Playing with inspiration from the Swinging 30s, these cool cats will have you in stitches with a small twist on the long form improv Chicago is famous for.

Our cast turns audience-suggested parties into long form improv extravaganzas. Each week, one of our performers takes the reins as the party host, leading you through the celebration. Meanwhile, our quirky characters stop at nothing to ensure they get exactly what they want out of the party.

Join the CinEvil Society as they search for the world’s most evil film! Be the test audience as your villainous host screens a select horror movie to see if it can terrify you into submission. Unfortunately, the aging VHS tapes used to copy these fiendish films from late night tv in the 80’s have degraded over the years, and the missing scenes must be re-created by a cast of damned improvisers freshly summoned from the netherworld. Even though they’ve never seen the original movie. What creature will feature next? The hungry C.H.U.D.? The groovy Ghoulies? Or the big balls of Phantasm? Dare to buy a ticket to this late night fright and find out!

Step into the villa for Prov Ur Luv 2 Me – Season 2.

After a hot and spicy season one, a whole new cast is back and ready to find love. Heads will turn, comedy will be had, and love will be found…probably. Watch as a cast of fit, flirty singles crack on, recouple, and get feisty in their quest for finding the one. With audience-driven twists, spontaneous game challenges, and enough drama to fill anyone’s teacup, every show is a brand-new villa of chaos.

Will they find true love—or just make it through the next elimination? Either way, you’ll be drawn in by high-stakes, love-fueled spectacle.

Back for its 3rd season! Premier Chicago standups fuel the imaginations of some of the city’s best improvisers. Come see how they layer it on.

Featuring:
Laz Patillo Becca Nix Tham Kayla McCaffrey James Fisher JOY! FLEX

Sleeping Giant is a solo show written and performed by local comedian and tall person, Tom Rhoads.

Audiences across the country have described this show as a delightful journey into the mind of a gentle giant.

Millennials take on Generation X in a battle to see which generation is funnier. The audience votes at the end of the show. Featuring some of the best comics in Chicago, Hosted by Todd Glover

Are you ready to laugh? Sunday nights in August come see a Stand-up Comedy Show with local Chicago comics.

Go All-In on longform improv with host team Lavalier. Six teams play for a chance to win completely worthless prizes awarded by our esteemed panel of improv judges, followed by a performance by the judges themselves. Seven teams, six weeks, two hours of hilarious improv comedy. Nothing has been scripted or prepared in advance. It will all be made up before your very eyes!

The Chicago Comedy hour is a comedy variety show featuring sketch, improv and stand up from some of the best up and coming comedians in Chicago.
Featuring: Danny Neary, Sean Delaney, Caroline Hendricks, Ally Neff, Abe Arnold