Windy City Comedy Fest, Aug 6–9

Windy City Comedy Fest opened in Chicago on Thursday, August 6, with four days of stand-up shows booked across venues including The Den Theatre, Lincoln Hall, Laugh Factory Chicago, The Annoyance Theatre, iO Theater, Newport Theater, Reggie’s, de Maat Studio at The Second City and The Lincoln Lodge. Choose Chicago listed the event as running through Sunday, August 9, and described it as a citywide showcase of Chicago’s stand-up scene alongside nationally touring comics. The festival’s own website said the 2026 edition is its second annual event and called it Chicago’s largest stand-up festival. The site said tickets for all shows were on sale. ### Which venues are part of the festival this weekend? Choose Chicago’s event listing named nine participating rooms and theaters spread across the city, with The Den Theatre and Lincoln Hall among the most prominent stops on the schedule. The city tourism group said the festival would celebrate Chicago’s stand-up scene across those venues from August 6 through August 9. (choosechicago.com) The festival website listed a broader venue roster that included The Den Theatre, The Lincoln Lodge, The Annoyance, Lincoln Hall, de Maat Studio Theatre at Second City, iO Theater, Newport Theater, Reggie’s and the Laugh Factory, and said the event would use “the best venues in Chicago.” The same site said the festival would feature rising comics from around the country. ### How big is the lineup? (choosechicago.com) The Den Theatre’s event page for Thursday’s opening show said the festival would feature more than 50 comedians across 10 Chicago venues. That count is the clearest public number attached to the 2026 event in ticketing and venue materials reviewed on Thursday. Choose Chicago’s listing named nationally touring headliner Isabel Hagen and veteran Chicago comic Pat Tomasulo among the billed performers. (windycitycomedyfest.com) The city listing also said the event would mix local acts with visiting comics over the four-day run. ### What is happening on opening night? Thursday, August 6, began with an opening-night headliner set from Isabel Hagen at The Den Theatre, according to The Den’s calendar and ticketing pages. (thedentheatre.com) The venue described Hagen as a comedian and classically trained violist who has appeared on “The Tonight Show Starring Jimmy Fallon,” “The Late Show with Stephen Colbert” and “After Midnight.” (choosechicago.com) The Den’s ticketing page showed Thursday availability for the Hagen show, with a listed price of $19.25 at the time of the crawl. The venue page also said the event carried a two-item minimum. ### Where can readers find the full schedule? Windy City Comedy Fest’s ticket page said readers could browse shows and buy tickets for the August 6-9 run through the festival website. The page described the event as taking place across Chicago venues including Lincoln Lodge and Second City. (thedentheatre.com) Choose Chicago also published the festival as an event series, with separate entries for Thursday, August 6, through Sunday, August 9. (tickets.thedentheatre.com) Those listings direct readers to event details for each day of the run. ### What happens next after Thursday? Sunday, August 9, is the final day listed in the Choose Chicago event series for Windy City Comedy Fest 2026. Readers looking for remaining tickets, daily show times and venue-by-venue listings can find them on the festival’s shows page and the Choose Chicago event pages for the August 6-9 series. (windycitycomedyfest.com) (choosechicago.com)