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.
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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, Jayson Acevedo, 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.
🎟️ Limited seating available. Secure your spot now.
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:
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, Aaron Bell, E.J. Masicampo, Tommy Saxton, Yoni Heisler, Darrick Ervin II, 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, 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
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, Jayson Acevedo, Shawna Blake, James Stanley, Ariel Julie, and the legendary Dwayne Kennedy closing out the night.
Comedy Heavyweights
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, Jon Boyd, Travis Stevenson, 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
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, 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.
The Blackout Diaries
True stories. Ridiculous nights. Bad decisions.
The Blackout Diaries is a nationally acclaimed storytelling comedy show where comics (and sometimes civilians) tell true drinking stories—and then the audience can ask questions. It’s part stand-up, part support group, and fully hilarious.
As part of Windy City Comedy Fest 2025, this special edition is hosted by a Blackout Diaries producer and features six comics baring it all with booze-soaked tales:
Christine Ferrera, Kristina Feliciano, Ben Frank, Jamie Campbell, Chris Cyr, and Yoni Heisler.
Drink it in. Then try to remember it the next day.
Laughter Hours
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
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.
A-List Laughs
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, Mike Shanks, Travis Stevenson, Hannah Beck, Eliza Butler, Joey Cerone, Avril Granato, Paul Blomeyer, and Knute Gregory.
Expect punchy sets, magnetic energy, and a perfect way to spend your Saturday afternoon.
Hecklers’ Happy Hour
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
This is the 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.
Kevin & Hell: Album Recording
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.
Hosted by Ariel Julie, this late show features a fire lineup:
Bob, Tito, Kieffer, a special guest spot (TBA), 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.
Down & Dirty
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
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, Rachel Hall, Johnny Mocny, Mitchell Potts, Carrie Ross, Dan Treadway, Paul Blomeyer, Knute Gregory, and a surprise Vouch Spot.
The fest may be winding down, but this show is just getting started.
Caffeinated Comedy
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, Darrick Ervin II, Edward Bell, Dr. Keith West, and Dan Garcia.
It’s Sunday stand-up with espresso energy.
Roast Battle Chicago at the Den
🗓 August 10, 2025 | 🕖 7:00 PM | 📍 The Den Theatre Comedy Club
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
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.
🎟️ Link: Coming Soon
Gold Standard Comedy
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, Travis Stevenson, Jayson Acevedo, Leah Kayajanian, Mitchell Potts, Chris Cyr, and Edward Bell.
It’s classic Chicago comedy with a festival twist.
Tickets coming soon!