Clued In returns to Second City’s UP! Comedy Club with a fresh improvised murder mystery that blends sharp wit with classic Agatha Christie–style suspense.
High Stakes Productions reunites with The Second City for Clued In: Where There’s a Will, There’s a Way, an immersive 90-minute theatrical experience running Thursdays and Sundays throughout October, capped off with a special Halloween performance on Friday, October 31 at 8 p.m.
Following last year’s sold-out run, the new installment takes audiences into the tangled dynamics of a family estate, where rivalries and hidden agendas come to light. Each performance begins with an audience suggestion of an inherited object that inspires the mystery. From there, the ensemble builds a full investigation in real time, with every twist and accusation unfolding on the spot.
“It’s time to celebrate spooky season the Second City way — with an improvised experience serving up murder, intrigue, and laughs for days,” said Jen Ellison, creative director of The Second City. “After the astounding success in 2024, we’re thrilled to bring back High Stakes Productions for another Halloween show with more performances.”
A Natural Partnership Between Comedy and Narrative Improv
The collaboration between Second City and High Stakes Productions has become a Halloween staple. For 65 years, The Second City has set the standard for improvisation, serving as a launch pad for generations of comedic talent while continuing to innovate across its stages. High Stakes Productions brings a distinctive approach to improv — blending classic genre storytelling with theatrical precision. Its members are veteran performers from Second City’s Main and e.t.c. stages, TourCo, Annoyance, iO, Victory Gardens, Steppenwolf Garage Rep, Broadway in Chicago, and more.
Together, they deliver a show that combines Second City’s comedic legacy with High Stakes’ narrative-driven edge. Last year’s Clued In transformed a simple party invitation into a night of intrigue; this season’s theme dives even deeper into the drama of inheritance, power, and family secrets.
An Immersive Theatrical Experience
True to High Stakes’ style, the evening begins the moment guests step through the door. Pre-show elements — from themed cocktails to estate-inspired décor — create an atmosphere that pulls audiences into the mystery before a single scene begins.
“Where There’s a Will, There’s a Way proves that every family is of sound mind… until the bodies start piling up,” said Caleb George, artistic director of High Stakes Productions. “It’s an honor to get Chicago ready for Halloween with a show that immerses attendees the moment they walk into the theater.”
Chicago’s Top Improvisers on Stage
Each performance features a rotating ensemble of seven performers from High Stakes’ roster, known for their skill in weaving narrative arcs on the fly. The company has built a strong following with shows like HitchCocktails* at The Annoyance Theater and the ongoing Clued In series at Second City. Audiences can expect a fast-paced, unpredictable mystery every night.
Show Details
Clued In: Where There’s a Will, There’s a Way
Location: Second City’s UP! Comedy Club, 230 North Wells Ave, Chicago, IL 60614
Dates:
- Thursdays at 7:00 p.m. — Oct 2, 9, 16, 23
- Sundays at 4:00 p.m. — Oct 5, 12, 19, 26
- Special Halloween show — Oct 31 at 8:00 p.m.
Tickets: $30
Tickets and info here
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