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The Windy City Comedy Fest Is a Lollapalooza for Laughs Comedy-lovers will revel in this four-day festival founded by Ariel Julie, featuring more than twenty shows across nine of the city’s most iconic comedy venues.

by Carl Kozlowski | August 5, 2026

by Carl Kozlowski
August 5, 2026September 4, 2026Filed under:
  • Comedy
  • Recommended Comedy Shows
A woman with long curly hair, glasses, and visible arm tattoos is holding a microphone and speaking on stage, smiling against a dark background.

Ariel Julie, founder of the Windy City Comedy Fest

Summer is a hot season for festivals in Chicago. Lollapalooza brought nearly a half-million music lovers together last weekend for four days of concerts that rocked the city. This weekend, comedy lovers get their chance to see an impressive array of fresh talent, when more than fifty rising comics come together for the second-annual Windy City Comedy Fest.

With more than twenty shows across nine of the city’s most iconic comedy venues, the fest will bring plenty of laughs. Plans include a kickoff show by Isabel Hagen (“The Late Show with Stephen Colbert,” “The Tonight Show Starring Jimmy Fallon”) at the Den Theatre Thursday night as well as a taping by longtime local favorite Bob Keen for his new comedy special “Shots Fired” at Lincoln Hall on Saturday. It will also feature educational panels designed to teach local comics the essentials needed to succeed on the business and social media end of the industry.

“The sole purpose of the festival is to elevate comedic artists. We want to give people a chance who maybe don’t have 50,000 followers or have representation or a rich dad to push their clips or algorithms or the money to secure a social media package that can lead to a following,” says festival founder Ariel Julie, whose fifteen-member panel of judges watched more than 600 video submissions to pick the final fifty performers. “We really have a blind judging process. If you submit your clips, we will watch and judge you not on your followers, not your background, just the quality of the clip you sent. We wanted to elevate those talented voices and give those people an opportunity to be seen by industry experts, and Chicago audiences, which I think are some of the greatest audiences in the country.”

Julie launched her own comedy career six years ago and has seen other attempts at comedy festivals fall flat, but she used her career background in theater production, stage management and nonprofit event planning as well as an ace five-member support team to help last year’s inaugural edition fly. In addition to overseeing the planning and production of the fest, she will be a prominent face in it as well, as she will MC key shows every night—while her husband and fellow comic Bob Keen also gets to shine at his special taping.

A man with wavy hair, wearing a red Adidas jacket, holds a microphone and speaks on stage. There is a partially visible logo or artwork in the background.

Bob Keen

In addition to four industry showcase shows, where multi-comic lineups strut their stuff for industry producers, agents, managers and talent scouts, the fest will spotlight some of Chicago’s most popular themed shows.

“Among our special shows, we have ‘Wigs,’ a fabulous monthly show at the Lincoln Lodge where comics perform their sets while wearing ridiculous wigs, which sounds so simple but it’s actually hysterical and it’s so fun,” notes Julie. “We also have ‘Ha Ha Ha to Hell’ at Reggie’s on Saturday night, which is a much darker-themed show geared toward audiences that are not afraid of an edgy or really dark kind of bit.

“We also are partnering with the ‘Blackout Diaries,’ where comics specifically talk about a drunken night out and they can tell their story accompanied with pictures and images in a Google slide. There’s an audience Q&A after the story too. And Bob and I, every Friday night, produce a show at Lincoln Lodge called ‘Laughter Hours,’ where there’s live jazz and comics do regular sets, but then they come back up onstage and make up jokes from audience suggestions.”

For his “Shots Fired” special, Keen is promising a rapid-fire fusillade of funny where he aims to bring plenty of bite to his material.

“I don’t shy away from being divisive, and I do enjoy taking an audience or a listener or whoever into places like ‘Let’s entertain the bad thought without believing the bad thought,’” explains Keen. “I just go for the jugular, and not in an edge-lordy way, like I have to talk about this because it’s like the bad boy thing to do. I just don’t think clean. I also hit politics with a satire kind of vibe. I enjoy playing with unpleasantness as subject matter, and then going somewhere with it. I like it spicy. And what better city to be spicy in?”

The Windy City Comedy Fest takes place Thursday, August 6 through Sunday, August 9 at venues throughout the city. Tickets and more here. 

Tagged:
  • Ariel Julie
  • Bob Keen
  • Den Theatre
  • Isabel Hagen
  • Lincoln Hall
  • Lincoln Lodge
  • Reggie's

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