Looking for a Stand-up Comedy Open Mic that’s a supportive room and always a good time? Look no further than the Ya'll Mic. Whether you’re a seasoned comic, an improvisor who’s always wanted to try standup, or you just decided that today’s the day for your first open mic (kudos) – The Ya'll Mic is a great venue to workshop your bits. The show is every Tuesday from 5:30pm – 7:30pm. Signup is online and the signup sheet is posted on Facebook & IG on Mondays. The list is emailed out a few hours before the show. Comics get 4 minutes of stage time (and a lifetime of memories.) While all are welcome, the room prioritizes BIPOC, LGBTQ+, and Femme comics. Come laugh with us!

Open Stage is an opportunity for anyone to get on stage and try out whatever they're currently working on - standup, sketch, songs - you name it. At Open Stage anything can happen and it usually does!

Every Wednesday, this group of Annoyance Program graduates performs The Insignificant Mile, a creative twist on a classic form in which players create a strip mall through audience suggestion. Each show features four unique locations, and a brand new cast of characters that exist in the world they created. With new guest openers every week, the Insignificant Mile is sure to leave a significant impact on audiences!

Press Start: An Improvised Musical is a hilarious, high-energy full improvised musical inspired by the games you know and love. Each show, our cast creates a brand-new adventure on the spot using audience suggestions, complete with original songs, unforgettable characters, epic quests, and plenty of unexpected twists. From fantasy kingdoms and cozy villages to space battles and chaotic multiplayer mayhem, no two shows are ever the same. Whether you're a hardcore gamer or just love comedy and live theater, Press Start is a one-of-a-kind experience that turns the magic of games into a fully improvised musical adventure. Grab your party and get ready to press start.

Fun in Moderation is a New York City–based sketch comedy team featuring Kendall Bowden, Austin Elias-de Jesus, Syd King, and Nick Ryan. With backgrounds in UCB, stand-up, and character performance, their work focuses on character-first, game-driven sketches. The group has performed at NY Comedy Festival, SF Sketchfest, Caveat NYC, Asylum NYC, Austin Sketchfest, Philly Sketchfest, and was recently featured in The New Yorker (a surprise to them, too). Past openers include: Adam Conover, Vannessa Jackson, Dan Toomey, Moss Perricone, Maddie Wiener, and many more!

Day jobs are just for material, right? Odd Jobs uses these comedians’ offices, co-workers, and customers as inspiration for all new characters. Come see Odd Jobs for a variety of characters and funny stories from some of Annoyance’s best performers.

Enjoy an evening of off-the-cuff improv with some of the best emerging talent in the Chicago area. Fire & Beer is a fully improvised comedy show that explores the dark sides of life, relationships and human beings. The show features the Annoyance House Ensemble who excel at both long- and short-form improv. You can expect lots of laughs during this unpredictable improv show.

They take edibles. Then they improvise. There's a 'too-high' button, for when it gets too crazy.

See how short form improv works and even try it out yourself! This short form jam is open to Annoyance students and other improv performers. Join us!

You’re (un)invited! Uninvited is a fully improvised event-based disaster in three acts. The audience supplies the suggestion of why we’re gathered, and then we show you what wackiness and whimsy unfolded before, after, and then during the event. Join us for a one-hour chaotic descent into why we got ourselves Uninvited.

An LGBTQIA+ themed variety show featuring some of Chicago's strongest and most diversely hilarious voices!

Throw out your boredom and come see Stardom Awaits! Our cast of contestants compete to be the Biggest Star of them all! Each round of short form games is an opportunity for them to Win! Stardom Awaits is sure to be the highlight of your week. Brimming with enthusiasm and entertainment!

This is one of four official Industry Showcases at Windy City Comedy Fest 2026—where selected performers take the stage in front of bookers and industry professionals from across the Midwest. Designed to spotlight top talent from the festival, this showcase brings together comedians ready to be seen, booked, and remembered. By bringing industry to Chicago, Windy City Comedy Fest is helping shape the future of the Midwest comedy scene—connecting performers with real opportunities on a regional stage. Hosted at the Annoyance, this is a high-stakes, high-quality show.

After suffering a lung collapse in April, comedian Luke Herman revels in what’s left of his life with amazing and unholy guests. This variety show features improv from Hail Marys Comedy (with guests Ally Montgomery and Melina Arevalo) and standup from Luke Herman, Isabella Sinisterra, Hannah Beck, and Sam Rocha.

Kath Courtney and Rockie Wenrich are: Father Figures! Two dudes with the ability to fix your car, be fuckable, and die before you really get the chance to understand them. Special thanks, as always, to Chelsea Matkins. Made for fathers and DILF-enjoyers everywhere.

The Annoyance's very own musical ensembles. Every Tuesday at 8pm, two groups improvise brand new musicals based on audience suggestions. Featuring Musical Director Lisa McQueen and starring the Annoyance Musical Ensembles. Follow us on instagram: @tuesdaymusicalimprov

Rachael Mason and Connor Gorman, two very smart idiots, come out of retirement to improvise a one act play.

You've been summoned...to laugh. Jury Duty is a fully improvised courtroom comedy where the only thing on trial is sanity itself. Each night, the cast creates a brand new legal disaster based on audience suggestion, questionable logic, and total chaos. Watch as the foreperson loses their mind, evidence makes things worse, and deliberations go off the rails. No script, no rules, no justice. Just comedy The trial is fake, the laughs are real

Lost Realms features some of the top musical improvisers in the city coming together to create an hour long sci-fi, fantasy, or horror musical based on common genre tropes, themes, and of course, audience suggestions.

Missed Call is a premiere Chicago comedy group that writes and performs an entirely new sketch show every Friday.

See a collage of character studies, scenes, songs and maybe even some audience interaction, all written in a week by some of Chicago’s most accomplished comedians. The “Holy Fuck Comedy Hour” is a curated hour of eclectic, comedic material written in a week with no rehearsals. Featuring a powerful collective representing a wide cross-section of the Chicago comedy community, the material varies every week.

Al's a new gay in Chicago looking for love in the big city when he bumps into the most beautiful man he's ever seen on the streets of Northalsted one night. Desperate to make his acquaintance, Al follows him into the legendary bathhouse Steamworks. As he makes his way through the maze of jacuzzis, slings, gloryholes, and fuck benches, Al makes a wild group of friends who help him discover what love might really mean when everyone's covered in cum.

Magician Jay Collen performs selected tricks covering a century of close-up magic created by Chicago magicians. Audiences are limited to 30 per performance so that everyone can experience the magic up close. Audience members are encouraged to participate in discussion about the each trick and its Chicago history. Jay performs performs extensively, is the Senior Magic Teacher at Magic, Incorporated, has written acclaimed books on magic, and is a magician member of the famous Magic Castle in Hollywood.

Annoyance students let loose in this student improv jam - all Annoyance students are welcome! A great opportunity to meet other members of our improv community.

Step into the one glamorous but now lovingly frayed Blue Velvet Lounge, where the only thing not improvised are the jazz standards crooned by lounge singer Seth Lowery. As Seth’s velvet voice fades, the ensemble sweeps in, spinning spontaneous scenes inspired directly by the songs just performed. One moment, you’re eavesdropping on the eccentric regulars tucked into the lounge’s candlelit corners; the next, you’re whisked far beyond the club to follow the unexpected lives of the characters you just met—bartenders with secret ambitions, mysterious strangers with tangled pasts, and dreamers who stepped into the Blue Velvet for reasons they can’t quite explain. Playful, surprising, and steeped in a retro-cool vibe, this show blends live music and improvised storytelling into a one-of-a-kind night where every note inspires a new twist—and every visit to the Blue Velvet reveals something you’ve never seen before.

After nearly 10 years of performing together, Hails Reeves & Matty Vergun bring out some of their old favs, as well as brand new sketches and characters. These people are fucked in the head, please consider witnessing for one night only, as g-d intended.

Come join us as we explore different historic moments and blend together factual storytelling with creative and witty moments that were never documented. Each show will cover a different event that is researched and studied. We, then, take that information and improvise everything else that was lost to history.

Sharp. Polished. Unmissable. Gold Standard Comedy lives up to its name with a lineup of some of the finest comedians at Windy City Comedy Fest 2026. Every performer is a proven crowd favorite—delivering stand-up that’s clever, confident, and consistently funny. This late-night showcase brings together top-tier talent for a smooth, high-quality comedy experience that highlights the best of the fest.

Welcome to JUICY, Chicago’s premier gossip-based comedy show. Each month, a cast of HOT improvisers spill their own real stories, anonymous audience confessions, and perform fast, filthy improv. Known for a cast with undeniable onstage chemistry, this show is the ultimate Wednesday night out! What happens at JUICY stays at JUICY… but you’ll be dying to tell everyone you were there.

Are you and your improv team looking for another place to get on stage? We've got a warm and supportive room ready to give you laughs and claps! Bring your own team to Annoyance on Tuesday nights to get a rep in and giggle. If you don't have a team to bring, no worries! There's a mashup team and we're happy to throw you on it! Signups are at 8:30PM and we'll hit the stage at 9:00PM. See you every Tuesday!

Tiny Idea Live! is a sketch comedy show by Ann Nelson, Eva Nemiroff, and Hrannar Björnsson, featuring all-new live sketches and never-before-seen videos! Tiny Idea’s videos have gotten more than 100 million views and have been featured in Vulture. They currently write for Dropout’s Game Changer and Make Some Noise. The trio has a combined age of 80 and has been described by a TikTok comment as “three of the most average-looking people I’ve ever seen.”

Inspired by the classic movie and hit FX show "Fargo", Duluth takes audiences into the world of true crime in the Midwest. The cast will improvise a story of murder, malfeasance, and general mayhem, all set against the backdrop of an audience member's hometown. Complete with cops, criminals, and the everyday townsfolk who get caught in between, this show contrasts horrible crime with "Minnesota nice".

New forms. New Players. Big Laughs. Every week is a new and different show. So what you see, no one else will see.

A Chicago based improv comedy show and drinking game based on the works of Alfred Hitchcock. Based on an audience suggestion, the cast weave together an intricate Hitchcock-like drama, while holding true to the amount of drinking shown in his movies. You'll barely be able to stand the suspense, and the cast will barely be able to stand.

Mentalism meets improv comedy in the entirely unique form created by Annoyance founder Mick Napier. There is truly nothing else like it.

An hour long comedy show featuring some of Annoyance Theatre’s best and funniest. Show Runner: Hails Reeves

Actress and comedian Gavin Connell takes you through her coming of age, reflecting on her trans-ness through every embarrassing story. From school crushes to college secrets to theatrical misadventures, take a walk down memory lane with this fresh, shocking, interactive, at-times musical standup show!

Lt. Love Dr. Hotty McTotty has traveled back in time from 2075 on a mission to save human connection.. before it’s too late. Through a series of drills like small talk, eye contact, speed dating, and friendly banter, audiences will rally together to combat the loneliness epidemic and our increasingly isolated reality. This hilarious, heartfelt, and surprisingly impactful show encourages you to make friends, disconnect from the digital world, and rediscover what it means to be human, if only for a night. "The beating heart of Fringe comedy" 4 stars, Broadway Baby "Wonderful" 4 stars, Eat More Art Vegas Fresh off of a four-city tour, and headed to Edinburgh Fringe, catch this show in Chicago for one night only!

Hundreds of miles offshore, a luxury cruise liner cuts through the Atlantic at double speed. At the helm? A megalomaniac captain in love with his own reflection & exploiting his beleaguered crew past their breaking point. As rebellion brews below, things are also heating up above deck! Love blossoms among thrill-seeking women, a heavy metal band grapples with their past & present, and a council of walruses issues a prophecy for destruction. Rudder Bullshit is a new play from the masterminds that brought you Docked and Loaded. Featuring original rock ballads that are guaranteed to make you put your lighters up! Hop aboard and strap in for what critics are calling "an edge in your seat adventure"! It's some Rudder Bullshit!

Join us for Comedian Cabaret: Show Tunes with Comedy Flair! It's a night of talented comedians cosplaying as Broadway singers! Chicago is just overflowing with talent, and there's not nearly enough stage time to see it all. That's why Comedian Cabaret began: to give comedians a chance to flex more than their improv and stand up chops. Love showtunes? Then this is the show for you!

Hail and well met, traveler! Grab a drink, put up your cloak, and I’ll tell you a tale. Escapades is a completely improvised choose-your-own adventure. Sprinkled throughout each story are opportunities for the audience to vote on what happens next. Whether we’re riding jetpacks on Mars or a unicorn through a gumdrop forest, you’re guaranteed a night of gasps, laughs, twists, turns, and daring rescues. Excelsior!

Andrew Sulfsted and Wyatt Menci felt the higher calling to be an Alderboy, a position in local politics that resides at the very bottom of influence. In order to build their way to the top, the two recruit talent from their ward to boost political sway and community swagger. Can the Alderboys save Lakeview East? Only if their constituents have the gumption they require. Or it may just save itself. Either way, the Alderboys are here to stay.

WOAH! NEW EVERY MONTH. A raucous. raunchy, sometimes juvenile but always funny sketch show that will make your daddy give your mommy a pearl necklace... to clutch. Get tickets now, they're selling faster than a Stewie doll at Spencer's. DM: @Antivirginclub proof you bought tickets and we will draw you boobs.

Screw the algorithm! Sketched Out is a digital sketch comedy showcase rebelling against short attention spans. Too weird for your average feed, this is the gold that never makes it past the social media gatekeepers. Join us for a night filled with digital sketches on the BIG screen and meet some of Chicago’s boldest sketch artists, from up-and-coming voices to seasoned comedy pros. Have a sketch you want to submit? Check out @SketchedOut_Digital for submissions