Historic Skokie Theatre Begins New Chapter as "The Skokie" Following $50,000 Village Grant
One of the North Shore's most recognizable cultural landmarks is preparing for a new era. The historic Skokie Theatre, which first opened in 1912 and has operated continuously as a theater for more than a century, is being reimagined as The Skokie—a community-focused arts and entertainment venue that will honor its history while introducing a fresh vision for live performances, creative programming, and cultural experiences.
Located at 7924 N. Lincoln Avenue in downtown Skokie, the 150-seat theater is being acquired from longtime owner Wendy Kaplan, who has operated the venue as MadKap Productions since 2014. Under new ownership, The Skokie is expected to reopen in late 2026 with a diverse calendar of events designed to bring artists and audiences together.
The project is led by two families with deep ties to the arts: José Pablo and Kristi Cantillo, alongside Chris and Monica Matsakis. Together, they envision The Skokie as an intimate gathering space featuring stand-up comedy, live music, jazz performances, storytelling events, improv, one-act theater productions, curated film screenings, ceramics and art classes, phone-free listening nights, lectures from local experts, and community gatherings.
José Pablo Cantillo brings more than two decades of experience in the entertainment industry, with acting, producing, and writing credits that include The Walking Dead, Sons of Anarchy, Mayor of Kingstown, Elysium, and Chappie. Chris Matsakis is a Chicago-area entrepreneur and stand-up comedian, while Kristi Cantillo and Monica Matsakis contribute backgrounds in visual arts, education, and storytelling.
The vision for The Skokie is rooted in a friendship that began nearly 30 years ago when José Pablo Cantillo and Chris Matsakis met as freshmen in Indiana University's Kelley School of Business Honors Program. What started as a college friendship has grown into a shared mission between two families who believe the arts have the power to inspire creativity, strengthen communities, and bring people together.
The restoration recently received a significant boost through a $50,000 grant from the Village of Skokie's Storefront Enhancement Program. Structured as a 60/40 matching grant, the Village will reimburse 60 percent of eligible restoration costs, up to $50,000, while the ownership team funds the remaining 40 percent. The grant will support improvements that preserve the theater's historic character while introducing thoughtful upgrades to the lobby, bar, seating, sound system, and its iconic marquee. The redesigned space will draw inspiration from classic Hollywood theaters and intimate speakeasy-style venues.
While the Village's investment provides an important foundation, organizers say community support remains essential. The Skokie has launched an Indiegogo crowdfunding campaign to help fund additional renovations, upgraded production and sound capabilities, expanded programming, seating enhancements, and the long-term preservation of the historic theater.
"This isn't just about reopening a theater. It's about creating a place where people can connect, celebrate creativity, and experience something special close to home," said Chris Matsakis. "We want The Skokie to feel inspiring, approachable, and alive the moment people walk through the doors."
Monica Matsakis added, "There is so much talent and creativity in this area, and we want The Skokie to be a home for both emerging and established artists. We're creating a place where audiences can laugh, discover new voices, and make lasting memories together."
José Pablo Cantillo will help shape the venue's artistic direction by drawing on his entertainment industry experience and relationships to bring nationally recognized performers and unique programming to Skokie.
"Our goal is to make The Skokie a true cultural destination," Cantillo said. "We want artists to be excited to perform here and audiences to know they can expect something memorable, intimate, and authentic."
In addition to live performances, future plans include an upstairs private screening room and members-only lounge for artists and creators, as well as weekend events such as weddings, recitals, dance parties, and quinceañeras.
Unlike many larger entertainment venues, The Skokie is being developed with a community-first approach rooted in local support, accessibility, and a shared passion for the arts. Supporters of the Indiegogo campaign will become founding members with opportunities to receive opening night tickets, exclusive experiences, recognition opportunities, classes, and a permanent place in the theater's history.
"We truly want people to feel a sense of ownership in this space," said Chris Matsakis. "This theater has meant so much to so many people over the years, and we believe its future should be built together."
As restoration work continues, The Skokie aims to preserve more than a century of history while creating a vibrant destination where creativity, culture, and community come together for generations to come.
Learn More
For programming updates, grand opening announcements, and future events, visit www.TheSkokie.com.
Follow The Skokie on Instagram and Facebook for restoration updates, behind-the-scenes content, and upcoming event announcements.
Artists interested in performing at The Skokie can contact the team at booking@theskokie.com or info@theskokie.com.
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