Chicago audiences looking for something different this spring can catch 420 Shakespeare, a comedy performance that blends classic Shakespeare with improvisation and unpredictable live theater at The Second City. The show runs inside the De Maat Theater at 230 W. North Ave., with select performances scheduled through May 2026.

The premise is simple but intentionally chaotic: four professional actors perform a Shakespeare play while one cast member consumes at least 20mg beforehand, turning each performance into a live experiment where timing, delivery, and audience reactions can shift the show in unexpected ways. Because of that format, no two performances are the same.

Opening night takes place on April 20 at 4 p.m., leaning into the spirit of the holiday, while all scheduled performances throughout May begin at 9 p.m. Shows typically run about 90 minutes. Tickets are $34.20 and the production is strictly 21+ due to adult language, sexual humor, and cannabis references. The performance takes place in an intimate theater setting known for comedy-forward productions and late-night audiences.

Rather than presenting Shakespeare traditionally, the production leans into Chicago’s improv culture, combining scripted material with spontaneous moments shaped by performer energy and crowd interaction. The format reflects the city’s long-standing reputation as a hub for experimental comedy and alternative theater experiences.

Interest around the show tends to spike around 4/20 and weekend performances, and seating is limited inside the De Maat Theater, making advance tickets recommended for popular dates.

For Chicago residents and visitors looking for a night out that feels more like a live comedy event than a traditional stage production, 420 Shakespeare offers a fast-moving, unconventional take on classic theater — equal parts improv show, cultural parody, and late-night entertainment experience.