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!

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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.

Comedians are pitted in a head to head competition to write punchlines to set ups they are seeing for the first time. The audience votes on there favorite punchlines usining there smart phone and advances the comedians each round. Named Best of Chicago by Chicago Magazine!

After a sold-out run at Toronto and Edinburgh Fringes, musical comedian Anesti Danelis brings his hit comedy special to CHICAGO for one night only! In this hilarious standup musical comedy hour, Anesti asks ChatGPT to write him a show based on his life, and this is what we got…

“A thoroughly entertaining and idiosyncratic stand-up show with songs that are intensely relatable, absurd, and side-splitting”
— ★★★★ The Extra Mile

“Anesti Danelis is redefining comedy with Artificially Intelligent… pure comedic gold… What makes Danelis stand out from the crowd of musical comedians is his knack for blending personal experiences with universal humor. Whether he’s riffing on second-generation immigrant challenges or poking fun at queer stereotypes, his comedy strikes a chord that’s both hilariously relatable and broadly accessible.”
— ★★★★★ Parton & Pearl

*The Second City – Best Comedy Award Winner*
*Toronto Fringe – Patrons Pick Audience Choice Award*
*Critics Pick – The Toronto Star*

As seen on Just for Laughs, CBC’s The Debaters, CBC Radio’s Laugh Out Loud, and multiple televised GALA’s at the Winnipeg Comedy Festival, he’s toured sold-out shows across North America and the UK—earning accolades like “Top 8 Best Comedy Shows” at the Edinburgh Fringe Festival. Armed with a guitar, and keyboard, he takes on immigrant family life, millennial struggles, bisexual dating mishaps, and more.

Follow Anesti online:
@anestidanelis (Instagram, Tiktok)
@danelisanesti (YouTube).

“The Process” is a raw, hilarious, behind-the-scenes look at stand-up in motion. Every week, comics test new jokes, refine old ones and reveal the beautiful chaos of finding funny. No sets are final. No notes are off limits. It’s stand-up, mid-sentence. Come watch the mess turn into magic

YOU’RE INVITED…to bear witness to a fully improvised murder mystery. Six improvisers find themselves trapped on stage with a murderer, and nobody knows who the killer is. With a suggestion from the audience, a singular detective must unravel a completely unscripted plot of deceit, suspicion, and murder. Watch the actors keep track of facts, follow leads, and sniff out clues to nab the killer, all while you take in a comedy experience unlike any other. Savagely funny and shockingly intelligent, Clued In is “infectiously fun” (Marissa Oberlander, The Chicago Reader). High Stakes Productions collaborates with the world famous Second City to bring this thrilling and hilarious improvised experience to life. This is an invitation to a one-of-a-kind immersive theatre experience not to be trifled with — can you figure out whodunnit before someone else gets done in?

Summer is here! Wait…it’s gone already? Where did it go? Time really flies when there’s so much going on in the world. Don’t worry, we’ve got your back! Start your 3 day weekend off the right way by joining us in laughing at the world together!

Queers and Fears is a wickedly funny sketch comedy revue where the monsters are gay, the closets have skeletons, and the only thing we have to fear is our own internalized homophobia. From cursed hookups to ghost stories about being ghosted, this spooky celebration of queer survival blends sharp satire with blood-stained glitter. Come laugh, scream, and sashay into the shadows—because in this show, pride is a scream.

A fun, inspiring, funny, moving, and theatrically packed show with a familiar theatrical style intertwined throughout each scene. This show ventures through the voice of a woman staying grounded in herself through life’s rollercoasters, telling funny moments lived through a woman’s truth in 2025. With original SNL style monologing, musical theatre, hip hop parody’s, poetry, original jokes, dramatic characterization, and improvising with her friends. You will leave the show with your own way to persevere through your own memes of life finding humor even in hardships.

Rhythm and Riffs is a high-energy fusion of live music and longform improv, where each show features a different musical guest—that can range from rap, jazz, country, folk, full bands, and beyond—whose performance inspires a completely improvised comedy set. No two shows are the same. With a cast of seasoned performers and a spotlight on Chicago’s diverse music scene, Rhythm and Riffs feels like a concert, sounds like a mixtape, and plays out like your favorite night out.

Welcome to “Juicy,” the unapologetically sassy three-act experience where the only thing hotter than the gossip, is the cast. Consider this your warning: what goes down in this room, STAYS in this room. So buckle up. Our fierce host starts by leading a panel, where the cast dishes up their weekly dramas. The audience gets to join in via QR codes by sending in their wildest scandals and seek real-time advice. Next up, we turn to the “hot seat” where we spotlight a badass standup comedian, serving up a set that’s perfectly tailored for our raw, unfiltered vibe. And just when you think it can’t get any wilder, we dive into an improv explosion, using stories as our launchpad to the craziest, most feral tangents imaginable. Get ready to laugh, gasp, and spill your guts — this is “Juicy.”

Welcome to Short Story Time! A debut short-form improv show that
takes wholesome chaos to delightfully off-topic new depths.

Equal parts heartfelt and half-true, this short-form improv ride is filled with games, scenes, and soft-spoken wisdom that nobody asked for, but everyone needs.

Ecclesiastes famously said, “When it comes to one man shows, there’s nothing new under the sun.” Well, Ecclesiastes never saw DOM DOES 300. Don’t miss it as locally acknowledged actor Dominic Rescigno tackles the unthinkable: a solo, scene-for-scene retelling of Zack Snyder’s 2007 epic film 300. (Note this production will not feature Chris Laychak or Adriana Trajkovski, who are traitors and unfit for the stage.)

The Punxsutawney Beauty Pageant contains crazy contestants, wild talents, and eerie hosts. Join Husband and Wife, Alabaster White and Geenie Jean “The Beauty Queen” as they try to find the most “Beautiful Girl” in their small town through this rollercoaster ride of a showcase.

Low Key Lit Wednesdays is a new comedy show at the world famous Second City, which will feature improv and stand up comedy acts each week. You can expect some of the biggest names in comedy, locally and nationally, to perform in this amazing show. This is more than a comedy show, it is an experience. An experience, you don’t want to miss.

What if your favorite movie was set in Chicago? Flicks like Jaws, Titanic, and Trolls are deserving of sequels in The Second City, and we are here to provide just that. Come out and enjoy a night out where we improvise a movie sequel of your choosing! From dramas to rom-coms, we are open to all, so you never know what might happen next. The retelling and reimaging of your favorite characters from the cinema will happen live, leaving you to wonder if movie sequels really should exist. Take the night off to enjoy the next big summer blockbuster where, of course, there will be previews.

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.

Olympus Has Fallen (And it Can’t Get Up) is a sketchy retelling of your favorite Greek myths. As educational as it is explicit, this hour-long sketch show will take you on an outrageous journey through the myths, gods, and monsters of Ancient Greece. How many men can fit in a horse? What’s the worst that can happen if you marry your sister? Why are all the boy statues naked? Olympus Has Fallen (And it Can’t Get Up) will answer questions you never knew you had. Whether you’re a fan of Percy Jackson, or you had friends in middle school, this is the show for you.

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!

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!

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.

After chilling audiences across the nation, Yes, AHHH! returns this summer with a new improvised horror tale: Tourist Trap. The sun is shining, the roads are open—but not every getaway ends in paradise.

In this fully improvised nightmare, unsuspecting travelers find themselves in picture-perfect towns with unsettling secrets. Inspired by Midsommar, White Lotus, and Cabin in the Woods, Tourist Trap blends eerie laughs with creeping dread. It’s the summer trip you’ll never forget… even if you never make it home.

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!

Veteran Chicago improviser and current Second City faculty member, David Montgomery, performs with different improvisers each show. Sometimes it’s with an existing improv team. Sometimes it’s with fellow veteran improvisers or former students. Each Sunday night is different so come laugh and see who’s performing with David! There will also be 2 opening acts performing before David M & Friends.

Cheap laughs have never been cheaper! $15 gets you an all-you-can-laugh pass to this ridiculous R-rated sketch comedy romp. Coming straight off two SOLD OUT runs at The IO and The Den Theatres, OxyMorons presents their new show: Controlled Chaos. Join us for crazy characters, psychotic puppets and special effects that are so silly they’re practically perfect! Every week features a new special guest from the best up-and-coming comics in Chicago!

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

Hello Travelers! Welcome to RPG-13, the comedy company that combines role playing games with improvisation, where fate and funny collide! Join us as we invite a volunteer from the audience (maybe you!), to help them create their very own adventure! However, the random roll of the dice will decide how that adventure goes. Roll a 20, a glorious success! Roll a 1, a hilarious disaster! Come see how we roll, and enjoy your adventure!

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

Olde Style Stand-Up Comedy from Chicago’s Best Stand Up Comedians

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