Windy City Fest Opening Night: Luke Null
🎤 Windy City Comedy Fest Presents: Luke Null & Friends
📍 The Den Theatre Comedy Club
🕗 Thursday, August 7, 2025 | Time TBA
Former SNL cast member and musical comedy powerhouse Luke Null headlines this stacked showcase at the Den Theatre. Hosted by the delightfully unfiltered Ariel Julie, the show features high-energy sets from Anthony Bonazzo, Jamie Shriner, Ken Hamlett, and Brandon Kieffer — all bringing their unique voices to Chicago’s biggest comedy weekend of the year.
Expect characters, songs, chaos, and big laughs in one of the city’s most intimate comedy clubs. This is one you don’t want to miss.
Buy Tickets Now!
Opening Night at the Windy City Comedy Fest is a show you DO NOT want to miss!
Windy City Late Night Laughs Showcase
Windy City Comedy Fest at iO Theater – Late Night Laughs Showcase
August 7, 2025 | 10:30 PM | iO Theater, Chicago
Close out the night with an electric lineup at iO Theater during Windy City Comedy Fest 2025. Hosted by Chicago’s own Rebecca Joey Schwab, this late-night showcase is packed with some of the funniest rising stars and festival favorites from across the country.
The lineup includes:
Chris Cyr, Aaron Bell, Christine Ferrera, Brooks Sullivan, Jamie Campbell, Mitchell Potts, Hunter Hirsh, Hannah Beck, Matt Brown, and Queeny Bitch.
From smart storytelling to outrageous characters, this show promises a fast-paced variety of comedic styles that will keep you laughing into the night.
The Business of Comedy Workshop
The Business of Comedy: A Behind-the-Scenes Power Panel
So you’re funny — but do you know how to book, brand, and build a comedy career?
Join us for The Business of Comedy, a no-fluff, tell-all workshop where industry pros pull back the curtain on how the comedy world really works. Whether you're just starting out or leveling up, this panel gives you the tools to turn laughs into lasting opportunities.
Featuring:
Julia stoyanova (Booking @ Den theatre)
Vik Pandya (Full time comedian)
Orly K.G. (PR Professional)
David Sanchez (Talent agent)
Learn how to:
Get on the radar of clubs, theaters, and festivals
Navigate contracts, representation, and red flags
Build a brand before you "make it"
Monetize your comedy off-stage
This is your chance to ask bold questions, make smart connections, and walk away with a game plan.
Because funny is only half the job.
WIGS: Stand-Up Comedy in Wigs
WIGS: Stand-Up Comedy in Wigs – Windy City Comedy Fest 2025
August 8, 2025 | 6:00 PM | The Lincoln Lodge (Blue Room)
Start your Friday night with something delightfully unhinged. WIGS is a character-forward comedy showcase where every comic performs in a wig — and yes, it’s as chaotic as it sounds.
Hosted by Claire Parlette and produced by Ron Hexagon, this festival edition of WIGS features a stacked lineup of comics bringing bold characters, bizarre bits, and off-the-wall energy:
Ben Frank, Michelle Malizaki, Orly KG, Jordan Cerminara, Oumerisha, James Fisher Jr., Johnny Mocny, Edward Bell, Dr. Keith West, and Paul Blomeyer.
Come for the wigs. Stay for the deeply committed chaos.
Comedy Royalty at the Lincoln Lodge
Comedy Royalty – Windy City Comedy Fest 2025
August 8, 2025 | 7:00 PM | The Lincoln Lodge (Orange Room)
Bow down. Comedy Royalty is bringing a court of comedic killers to The Lincoln Lodge as part of Windy City Comedy Fest 2025. Hosted by the ever-regal Matt Brown, this showcase features a royally hilarious lineup of seasoned comics and rising stars ready to take the crown.
Featuring:
Christine Ferrera, Chris Cyr, Aaron Bell, E.J. Masicampo, Tommy Saxton, Brian Roe, Yoni Heisler, Dan Treadway, Ross Copeland, and the one and only Jamie Shriner.
From sharp stand-up to musical mayhem, this show serves top-tier comedy — no royal decree required.
Bad Momz at the Lincoln Lodge
Bad Momz – Windy City Comedy Fest 2025
August 8, 2025 | 7:30 PM | The Lincoln Lodge (Blue Room)
They’ve got snacks in their purse, opinions on your dating life, and punchlines that hit harder than a toddler tantrum. Bad Momz is a powerhouse stand-up showcase featuring comics who are moms, moms-at-heart, or just giving strong mom energy.
Hosted by the bold and hilarious Orly KG, this lineup is stacked with fierce and funny performers:
Colleen Brennan, Kristina Feliciano, Amanda Cohen, Leah Kayajanian, Eliza Butler, Cindy Arena, Laura Hugg, Carina Magyar, Alysa Browne, and Claire Parlette.
These momz aren’t here to tuck you in — they’re here to crack you up.
Primetime Comedy
Primetime Comedy with Headliner Dwayne Kennedy – Windy City Comedy Fest 2025
August 8, 2025 | 8:00 PM | The Lincoln Lodge
This is the main event. Primetime Comedy brings some of the sharpest voices in stand-up to the stage for a Friday night showcase that delivers big laughs and even bigger energy. This show is in the Lincoln Lodge Red Room.
Hosted by the electric and unfiltered Queeny Bitch, this lineup features:
Adam Levine, Kadeem Fuller, Hunter Hirsh, Shawna Blake, James Stanley, Ariel Julie, and the legendary Dwayne Kennedy closing out the night.
Comedy Heavyweights
Comedy Heavyweights – Windy City Comedy Fest 2025
August 8, 2025 | 9:00 PM | The Lincoln Lodge
No filler—just hitters. Comedy Heavyweights is the Friday night knockout showcase featuring some of the sharpest joke writers and strongest stage presences of the fest. If you're looking for punchlines that land hard and comics who bring the heat, this is your show. This show will be in the Orange Room of the Lincoln Lodge
Hosted by the effortlessly cool Ken Hamlett, the lineup includes:
Mike Shanks, Jamie Campbell, Jon Boyd, Muhammad Saahir, Kristie Hayden, Joe Medoff, Jeff Klein, Kayley Horton, Aaron Putnam, and Rebecca Joey Schwab.
A full night of hard-hitting comedy. No weak sets, no mercy.
Top Shelf Comedy
Top Shelf Standup – Windy City Comedy Fest 2025
August 8, 2025 | 9:30 PM | The Lincoln Lodge
Looking for the best of the fest? Top Shelf Comedy is serving nothing but high-quality laughs from the finest comics handpicked for this premium lineup. No chasers, just straight-up funny.
Hosted by the fearless and funny Nina Kern, this showcase features standout sets from:
Scott Eason, Christine Ferrera, Aron Woldeslassie, Tommy Saxton, Carrie Ross, Avril Granato, Hannah Beck, Keaton Ford, Knute Gregory, Bob Keen, plus a surprise Vouch Spot—a comic vouched for by fest insiders, guaranteed to impress.
Come get a taste of the top shelf.
Laughter Hours
Laughter Hours – Windy City Comedy Fest 2025
August 8, 2025 | 11:00 PM | The Lincoln Lodge (Orange Room)
Late night gets jazzy at Laughter Hours, the smoothest, sharpest stand-up show of the Windy City Comedy Fest. With laid-back vibes and tight sets, this showcase is perfect for night owls who want their laughs served cool and clever.
Hosted by the effortlessly funny Ariel Julie, the lineup includes:
Jon Boyd, Bailey Pope, Adam Levine, Allan Fuks, and Joey Cerone.
Come for the jokes, stay for the vibe. It's the comedy equivalent of a midnight martini.
Hall of Famers
Hall of Famers – Windy City Comedy Fest 2025
August 9, 2025 | 11:30 AM | The iO Theater
Start your Saturday morning with legends in the making. Hall of Famers features a hall-of-fame-worthy lineup of festival comics delivering unforgettable sets to kick off your day of laughs.
Hosted by the sharp and sassy Kayley Horton, this all-star show features:
Colleen Brennan, Aaron Bell, Aron Woldeslassie, E.J. Masicampo, Kadeem Fuller, Carrie Ross, Allan Fuks, Jeff Klein, Shawna Blake, Yoni Heisler, and Keaton Ford.
Expect smart jokes, bold voices, and a brunch-adjacent comedy experience that’ll set the tone for your fest-filled Saturday.
Storytelling for Standups
Storytelling for Standups: A Workshop with Sean Flannery
Great stand-up isn't just punchlines — it's perspective. It's voice. It's a damn good story.
Join veteran comedian, producer, and author Sean Blair Flannery for a workshop that dives deep into the art of storytelling on stage. With nearly two decades in comedy, Sean is the mind behind the hit show The Blackout Diaries, where comedians spin hilarious (and often chaotic) true tales. He's also the author of Places I Can’t Return To — a memoir that proves comedy and catastrophe go hand-in-hand.
In this interactive workshop, Sean will answer questions like:
How do I know if a story will work on stage?
Where do punchlines live inside a longer anecdote?
How can I sneak storytelling into a tight 5-minute set?
What makes a storytelling show successful — and how do I start one?
Whether you're a joke machine looking to stretch out, or a comic with too many wild stories to know where to begin, this workshop will help you turn your real-life moments into unforgettable sets.
Physical comedy for Standups
Physical Comedy for Stand-Ups: A Workshop with Claire Parlette & Hunter Hirsh
Move over mic stands — your whole body is the punchline.
Stand-up isn’t just about clever lines — it’s about how you deliver them. Whether you’re a high-energy act or deadpan to your core, physicality can take your set from forgettable to unforgettable.
In this dynamic workshop, Chicago comedy scene standouts Claire Parlette and Beckett Kenny — known for their inventive, bold, and hilarious physicality — will teach you how to:
Use body language and movement to amplify jokes
Turn awkward silences into visual punchlines
Add physical “tags” to elevate bits without more words
Explore the line between stand-up and clown, without losing your voice
Build a unique, physical stage presence that stays with the audience
Expect laughs, movement, and exercises that get you out of your head and into your body. Whether you want to dial up your energy or just stop pacing like a trapped raccoon, this workshop will help you move with intention — and kill harder doing it.
Comedy isn’t just heard. It’s seen. So make 'em look.
A-List Laughs
A-List Laughs– Windy City Comedy Fest 2025
August 9, 2025 | 3:00 PM | The iO Theater
This lineup is stacked with nothing but A-listers — no red carpet required. A-List Laughs brings together a group of comics who are ready to bring down the house with sharp material and unforgettable stage presence.
Hosted by Chicago’s own Matt Brown, the show features:
Michelle Malizaki, Scott Eason, Hannah Beck, Eliza Butler, Tony Castro, Joey Cerone, Avril Granato, Paul Blomeyer, Delilah Orizaba, and Knute Gregory.
Expect punchy sets, magnetic energy, and a perfect way to spend your Saturday afternoon.
Hecklers’ Happy Hour
Heckler’s Happy Hour– Windy City Comedy Fest 2025
August 9, 2025 | 6:00 PM | The Lincoln Lodge
Ever wonder what it’s like to be on the receiving end of a heckle? Heckler Happy Hour flips the script and embraces the chaos. Produced by Yarnmaze and Katie Mark, this show celebrates comics who’ve survived — and thrived — under pressure.
Hosted by the fearless Claire Parlette, the lineup features:
Jon Boyd, Dan Treadway, Kristie Hayden, Joe Medoff, Jeff Klein, and Alysa Browne — a group of seasoned pros who know how to handle a rowdy room and still deliver killer sets.
Come for the comedy, stay for the unpredictability.
Headliner Showcase Featuring Kerryn Feehan
Headliner Showcase with Kerryn Feehan– Windy City Comedy Fest 2025
August 9, 2025 | 7:00 PM | Lincoln Hall
This IS A big one.
The Headliner Showcase brings the absolute best of the fest to one of Chicago’s premier venues. Expect powerhouse performances, big names, and a packed house of comedy lovers.
Hosted by the always dynamic Ariel Julie, this primetime lineup features:
James Fisher Jr, Ben Frank, Bailey Pope, and Ken Hamlett, with the legendary Kerryn Feehan closing out the night.
Gold Standard Comedy
Gold Standard Comedy– Windy City Comedy Fest 2025
August 9, 2025 | 7:30 PM | Annoyance Theater
Sharp. Polished. Unmissable. Gold Standard Comedy lives up to its name by showcasing some of the finest comics at Windy City Comedy Fest. Every performer is a certified crowd favorite — bringing you stand-up that’s clever, confident, and laugh-out-loud funny.
Hosted by the legendary Laura Hugg, this elite lineup features:
Scott Eason, Jordan Cerminara, Colleen Brennan, Xavier Smith, Leah Kayajanian, Mitchell Potts, Chris Cyr, Edward Bell, and Nina Kern.
It’s classic Chicago comedy with a festival twist.
Headliners Only
Headliners Only – Windy City Comedy Fest 2025
August 9, 2025 | 8:00 PM | The iO Theater
No openers. No fluff. Just pure headliner energy.
Headliners Only is the ultimate Saturday night lineup, packed with comics who know how to own a stage. These performers don’t need warm-ups — they are the main event.
Hosted by the effortlessly commanding Carina Magyar, the show features an all-star lineup:
Kristina Feliciano, Adam Levine, Amanda Cohen, Rachel Hall, Muhammad Saahir, Hunter Hirsh, Delilah Orizaba, Jamie Campbell, and Dr. Keith West.
Every set’s a closer. Come ready.
Kevin & Hell: Album Recording
Kevin Kellam Live Comedy Album Taping– Windy City Comedy Fest 2025
August 9, 2025 | 9:00 PM | Lincoln Hall
One part stand-up showcase, one part fever dream — Kevin & Hell brings the chaos, the crowd work, and the comedy straight from the depths of the fest’s wildest minds. You don’t want to miss this Chicago Comedy Legend’s first ever live album recording!
Hosted by Ariel Julie, this late show features a fire lineup:
Bob Keen, Tito, Brandon Kieffer, and headlined by Chicago’s own wrestling-loving wildman Kevin Kellam, who’s bringing 45 minutes of unfiltered comedic mayhem.
This show will sell out. You’ve been warned.
Celebrate this milestone in Kevin’s 10+ years performing in Chicago!
Kevin Kellam is a Chicago-based stand-up comedian, radio host, and content creator who mixes rapid-fire punchlines . By day, Kevin can be heard on Q101, Chicago’s legendary alternative rock station, where he delivers hot takes between tracks. He’s also created viral content and led audience engagement efforts for major outlets like Sportskeeda, WrestleZone, and Crave Online, with previous stints on-air at Rock 108, WIIL ROCK, and The X.
A Columbia College graduate, Kevin has worked with some of Chicago’s hottest comics since 2010, hosted the Fourstar Standups web series, and trained under SNL’s former head writer Michael McCarthy. Whether he's behind the mic or piloting a speedboat as a Navy Pier tour guide, Kevin’s always chasing the next punchline — and KEVIN & HELL is the one to catch.
No Filter Comedy
🎤 Windy City Comedy Fest: No Filter Comedy
🗓️ Saturday, August 9 | 🕤 9:30 PM
📍 The Annoyance Theatre | 🎟️ Get Tickets
Get ready for a no-holds-barred, uncensored, unapologetic night of stand-up with some of the boldest voices in comedy. Hosted by the fabulous Queeny Bitch, this lineup brings the heat and the hilarity:
Featuring:
Michelle Malizaki, Jon Boyd, Oumerisha, James Fisher Jr, James Stanley, Cindy Arena, Eliza Butler, Joey Cerone, Kirstie Hayden, and Shawna Blake
Whether it's brutally honest bits or fearless punchlines, this is the late-night show that doesn’t hold back. Come for the laughs—stay for the chaos.
Down & Dirty
Down ‘N Dirty– Windy City Comedy Fest 2025
August 9, 2025 | 10:00 PM | Lincoln Lodge
Leave the kids at home and your inhibitions at the door. Down & Dirty is a no-holds-barred stand-up showcase featuring comics who are bold, bawdy, and unafraid to go there.
Hosted by the devilish Grieco, this lineup goes all in with:
Aron Woldeslassie, Brooks Sullivan, Ross Copeland, Laura Hugg, Nina Kern, Avril Granato, Keaton Ford, and Hunter Hirsh.
If you like your comedy spicy, raunchy, and uncensored — this is the show for you.
Comedy Legends at Second City
Comedy Legends– Windy City Comedy Fest 2025
August 9, 2025 | 11:00 PM | The Second City
It’s late. It’s rowdy. It’s the final laugh of the night. The Late Night Showcase at Second City brings together a stacked lineup of comics who know how to keep the energy high, the crowd loud, and the punchlines rolling past midnight.
Hosted by crowd favorite Tito, the lineup features:
Mike Shanks, Ben Frank, E.J. Masicampo, Yoni Heisler, Rachel Hall, Johnny Mocny, Mitchell Potts, Carrie Ross, Dan Treadway, Paul Blomeyer, and Knute Gregory.
The fest may be winding down, but this show is just getting started.
Caffeinated Comedy
Caffeinated Comedy– Windy City Comedy Fest 2025
August 10, 2025 | 11:30 AM | The Laugh Factory
Comedy and coffee? Yes please. Caffeinated Comedy is the perfect way to wrap your weekend with sharp comics and strong brews. This late-morning lineup is packed with talent — guaranteed to wake you up with laughter.
Hosted by quick-witted fest favorite Carina Magyar, the showcase features:
Kristina Feliciano, Jordan Cerminara, Oumerisha, Amanda Cohen, Tommy Saxton, Leah Kayajanian, Cindy Arena, Edward Bell, Dr. Keith West, and Dan Garcia.
It’s Sunday stand-up with espresso energy.
Social Media for Standups
Social Media for Stand-Ups: Build Your Brand Without Selling Your Soul
A panel discussion featuring Chris Grieco, Kristen Toomey & Kerryn Feehan
In today’s comedy world, it’s not just about being funny on stage — it’s about knowing how to turn your set into scroll-stopping content. Whether you're trying to sell tickets, book shows, or just get your jokes in front of new eyeballs, social media can either feel like your best friend or a chaotic mystery.
Luckily, we’ve brought in three comics who cracked the code:
Chris Grieco – Comedian, producer of Roast Battle Chicago, and a master at turning clips into cult followings
Kristen Toomey – A powerhouse comic with over a decade in the game, known for her sharp stand-up and no-BS voice online
Kerryn Feehan – All the way from NYC, a hilariously fearless performer and podcast queen who's grown her digital audience into a real-world fanbase
Together, they’ve built huge platforms from scratch — and now they’re spilling everything they’ve learned.
You’ll get answers to real questions like:
How do I know what content to post from my set?
Do I cater to the algorithm or build my own lane?
How do I grow a following without losing my voice?
What apps, tools, and strategies actually work?
Whether you’re a clip-cutting machine or still terrified of TikTok, this panel will help you post smarter, grow faster, and find your audience — without becoming someone you’re not.
Because funny deserves to be seen — not just shouted into the void.
Roast Battle Chicago at the Den
Windy City Comedy Fest Presents: Roast Battle Chicago
August 10, 2025 | 7:00 PM | The Den Theatre
It’s not personal… it’s just hilarious.
Roast Battle Chicago is back and meaner than ever — with comics going head-to-head in brutal, brilliant insult matches. Hosted by Windy City firestarter Grieco and judged by a savage panel: Brandon Kieffer and Kerryn Feehan.
Six battles. No mercy. Just laughs.
🔥 Matchups:
Tito vs. Femi
Rebecca Jaffe vs. Tom Ryan
Bob Keen vs. Zach Albers
Tory Ward vs. Hannah Beck
AJ Leidig vs. Joe Medoff
Matt Sullivan vs. Evelyn Troutman
Come witness the best (and worst) things comics can say about each other — all in the name of comedy.
Comedy All Stars
Comedy All Stars – Windy City Comedy Fest 2025
August 10, 2025 | 7:00 PM | The Laugh Factory
Closing night calls for a lineup that shines. Comedy All Stars brings together a dream team of festival standouts for one final showcase of big laughs and high-level talent.
Hosted by the always sharp Anthony Bonazzo, this powerhouse show features:
Orly KG, Bailey Pope, Rachel Hall, Kadeem Fuller, Muhammad Saahir, James Stanley, Brooks Sullivan, Alysa Browne, and Allan Fuks.
Come celebrate the end of Windy City Comedy Fest 2025 with the best in the biz.
Dopamine with Kerryn Feehan
Dopamine Featuring Kerryn Feehan – Windy City Comedy Fest 2025
August 10, 2025 | 9:00 PM | The Laugh Factory
End the fest on a high with Dopamine — a handpicked showcase of comics guaranteed to hit your brain’s pleasure center. Featuring festival faves and a killer headliner to close out the weekend strong.
Hosted by comedy mainstay Aaron Putnam, the show features: Laura Hugg, Johnny Mocny, Ross Copeland, Joe Medoff, Delilah Orizaba, Tyler Buckingham and Mike Atcherson, plus a headlining set from Comedy Central, Netflix, and more’s: Kerryn Feehan!
You made it to the end. Now come laugh like your serotonin depends on it.
TICKETS BY VENUES
THE DEN THEATRE
THE iO THEATER
Windy City Late Night Laughs Showcase — Thu, Aug 7 – Fri, Aug 8 · 10:30 PM
Hall of Famers — Sat, Aug 9 · 11:30 AM
A‑List Laughs — Sat, Aug 9 · 3:00 PM
Headliners Only — Sat, Aug 9 · 8:00 PM
LINCOLN LODGE
WIGS: Stand‑Up Comedy in Wigs — Fri, Aug 8 · 6:00 PM
Comedy Royalty — Fri, Aug 8 · 7:00 PM
Bad Momz — Fri, Aug 8 · 7:30 PM
Primetime Comedy with Dwayne Kennedy — Fri, Aug 8 · 8:00 PM
Comedy Heavyweights — Fri, Aug 8 · 9:00 PM
Top Shelf Standup — Fri, Aug 8 · 9:30 PM
Laughter Hours — Fri, Aug 8 – Sat, Aug 9 · 11:00 PM – 1:00 AM
Heckler’s Happy Hour — Sat, Aug 9 · 6:00 PM
Down & Dirty — Sat, Aug 9 · 10:00 PM
LINCOLN HALL
Headliner Showcase Featuring Kerryn Feehan — Sat, Aug 9 · 7:00 PM
Kevin & Hell: Kevin Kellam Live Comedy Album Taping — Sat, Aug 9 · 9:00 PM
ANNOYANCE THEATRE
Gold Standard Comedy — Sat, Aug 9 · 7:30 PM
No Filter Comedy — Sat, Aug 9 · 9:30 PM
THE SECOND CITY
Comedy Legends at Second City - Sat, August 9 11PM
LAUGH FACTORY
Caffeinated Comedy — Sun, Aug 10 · 11:30 AM
Comedy All Stars — Sun, Aug 10 · 7:00 PM
Dopamine Featuring Kerryn Feehan — Sun, Aug 10 · 9:00 PM