Chicago Shows - The Second City

Jon Glaser’s debut comedy album, “Jon Glaser’s Soothing Meditations for the Solitary Dog” is the perfect remedy for those unfortunate yet unavoidable times that dog owners need to leave their beloved, anxious good boys and good girls home alone. Join Jon for a restorative evening of dog-centric relaxation and warm fuzzies. And with the VIP “Sip and Paint” ticket, you can come early and have a free glass of wine while you paint a portrait of your favorite pet! Portraits will then be discussed via Q&A’s with Jon during the show.

A Premium tickets gets you early entry to the event at 6:00pm, 1 complimentary glass of wine, premium seating, and watercolors and paper to paint a picture of your dog

Jon Glaser is an actor and writer who created, co-wrote and starred in the TV shows “Delocated,” “Neon Joe Werewolf Hunter,” and “Jon Glaser Loves Gear.” Most people recognize him as Councilman Jamm from “Parks and Recreation” and/or Laird from “Girls.”, and most recently as a sports podcast douchebag on “Running Point”. Other TV credits include “Law and Order SVU,” “Life and Beth,” “Single Drunk Female,” “Mr. Robot,” and “Wonder Showzen.” Film credits include “Trainwreck,” “Hustlers”, and the upcoming “Friendship”. Cartoon voice work includes “Dicktown” “Our Cartoon President”, and “Aqua Teen Hunger Force”. He appeared as Video Cowboy in the ESPN web series “Mayne Street,” and he created, wrote, directed and starred in a series of web shorts for Comedy Central called “Tiny Hands.”

Jon was most recently the head writer for “They Call It Late Night with Jason Kelce”. Other TV writing credits include “The Independent Spirit Awards” hosted by Aubrey Plaza, “Inside Amy Schumer,” “Late Night with Conan O’Brien” and “The Dana Carvey Show.” He has written several stories for The New York Times Magazine, and his writing has also appeared in ESPN The Magazine, Bicycling Magazine, The Onion A.V. Club, and on-line for New York magazine. His first book, “My Dead Dad Was in ZZ Top,” was published by Harper Perennial, and he wrote and directed the music video for Bob Mould’s “Star Machine.” He is also a Second City alum who was in the touring company, as well as the Mainstage ensemble show “Piñata Full Of Bees”.

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.

Life’s messy, weird, and downright absurd—but at least we can all agree on one thing: manners matter. Join our electric ensemble for a night of sharp-witted sketches, chaotic politeness, and absurdly well-mannered mayhem. This show is a ridiculous love letter to the weirdness we all experience when navigating Polite Society. We’d say “enjoy the show,” but you’re far too well-mannered not to.

A fast-paced, laugh-packed night featuring some of Chicago’s most killer standup comedians.

At Standup Bonanza, you can expect top-tier talent, relatable material, and immaculate vibes for an all-around good time!

A high-energy, laugh-out-loud sketch comedy show celebrating the vibrant and joyful world of queer life, all wrapped in unapologetic pride!

Join us for a special Commedia dell’Arte solo performance by Antonio Fava, an internationally renowned Actor, Author, Director, Teacher, Musician, Composer, and Mask Maker who has traveled from Reggio Emilia, Italy. This comedy features the classic character “Pulcinella” as he reflects on the harshness of life. The play will be performed primarily in English, with a variety of languages throughout. Run time 75 minutes.

Created and performed by Antonio Fava with supervision by Cecilia Di Donato. Special Guest: Claire Hart Proepper. Produced by Laughing Stock Theatre and presented in cooperation with the Istituto Italiano di Cultura di Chicago.

After scaring audiences across the nation, Yes, AHHH! is back for another improvised horror story. Spring is in the air, the flowers are blooming, and the open road calls. But not all destinations are as welcoming as they seem…

In Tourist Trap, travelers may stumble upon hidden gems—an idyllic town, a secluded festival, or an off-the-beaten-path attraction. The locals are so friendly. The customs are so charming. The experience is so immersive. But as the trip unfolds, the signs of something more sinister begin to surface. Will they make it out, or will they become part of the town’s dark traditions?

Inspired by folk horror/drama classics like Midsommar, White Lotus, and Cabin in the Woods, this fully improvised horror tale blends slow-burning dread with eerie humor, building to a finale that no one—audience or performers—sees coming. Whether you’re a seasoned traveler or just along for the ride, one thing is certain: in Tourist Trap, you will be staying… whether you like it or not.

Some of Chicago’s most talented Stand Up comedians deliver side splitting laughter coupled with answering live anonymous questions submitted by the audience via QR code.

Sero-Tone It Down: a 50 minute sketch revue with the goal of shedding light in some of the darkest areas of the human condition. We aim to highlight Mental Health Awareness month with a show run in May 2025 that explores the stigmas, day to day lives, struggles, and topics in general surrounding mental illness. With each performer looking to bring their unique voice to the stage and highlight Mental Health, Mental Illness’ they may encounter/deal with on a daily basis, we hope to create comedic conversation on topics otherwise ignored or altogether avoided. Additionally, we aim to outline and donate the ticket proceeds to Brave Space Alliance to give back where it matters the most. Come for the serotonin, stay for the conversation with Sero-Tone It Down!

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

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!