Music & Comedy, Theatre & Performing Arts
Dark Side of the Pillow Sketch Comedy Show May 7, 2026
The thoughts you have at 2 a.m.? We put them on stage.
Looking for a night out that feels unmistakably Chicago? Dark Side of the Pillow is a bold, laugh-out-loud sketch comedy show performed at The Second City—the legendary birthplace of some of the biggest names in comedy.
Created by a diverse ensemble of rising local talent, the show blends sharp writing, fast-paced scenes, and just enough edge to keep you leaning forward. It’s smart, a little unhinged, and deeply relatable—tapping into modern life, relationships, and the things we usually keep to ourselves.
Whether you’re visiting the city or planning the perfect Thursday night, this is your chance to experience Chicago’s next wave of comedy—live, intimate, and happening right where it all started.
Thursdays in May at 7:30 PM at DeMaat Theatre in Pipers Alley. Come see what Chicago is laughing about now.
