Faculty Spotlight: Celebrating 20 Years of Heart with Elizabeth Cunningham

At The Chicago Academy for the Arts, there are educators who shape curriculum, and then there are those who shape lives. For the past two decades, Elizabeth Cunningham, Assistant Principal and Director of Learning Resources, has done both.

Elizabeth Cunningham, Assistant Principal and Director of Learning Resources

As we celebrate Liz’s 20th year at The Academy, we honor not just her tenure but the profound and lasting impact she has had on generations of students, families, and the very spirit of our school.

A Journey That Began at Home

Liz’s story at The Academy didn’t begin with a job application — it began as a parent.

When her older son Brendan transferred into The Academy’s Music Department as a junior, the transformation was immediate and undeniable. After struggling to find his place in a traditional school setting, Brendan found something different here: purpose. He began arriving early, staying late, and perhaps most importantly, believing in himself.

It was Brendan who first saw what his mother would later become to so many others.
“You should work here,” he told her.

At the time, Liz had already built a meaningful career in special education, teaching in Chicago Public Schools and several therapeutic day schools, and even serving as a Due Process Hearing Officer early in her career. While deeply impactful, the work was demanding, and as her own children grew older, she began to consider a new path. A conversation with then-Head of School Pam Jordan opened the door.

In the fall of 2006, Liz stepped into that opportunity, joining The Academy as Director of Learning Resources. Today, she continues that work while also serving as Assistant Principal, approaching twenty years of service to the school.

A Foundation in Learning and Art

Liz’s approach to education is grounded in both artistic and academic rigor.

She earned her undergraduate degree in art from Loyola University Chicago, studying under Roberta Kozuch and Ralph Arnold, before going on to receive her Master of Education in Special Education under Dr. Martha Ellen Wynne. That dual perspective — artist and educator — continues to shape how she supports students today.

Her goal is clear: to ensure that every student has what they need to grow—not just as artists, but as thinkers. Just as importantly, she works to support faculty and staff, helping to cultivate the creative, vibrant community that defines The Academy.

A Family and a Life Shaped by The Academy

Liz’s connection to The Academy only deepened over time. Her younger son Colin followed in his brother’s footsteps, enrolling as a freshman in the Music Department. Through their experiences, Liz saw firsthand what makes an Academy education so powerful. It’s not just about training artists; it’s about teaching students how to learn.

That mindset of curiosity, resilience, and a willingness to embrace challenge shaped both of her sons into lifelong learners, far beyond the stage or studio. Today, Liz proudly counts being the parent of two Academy Music Department graduates among her greatest honors.

The ripple effects didn’t stop there. Liz’s husband, Tom, found his own creative path through The Academy community. What began as photographing dance performances grew into a professional photography career, sparked by the artistry and energy that surrounds our students.

A Community Where Students Are Known

Ask Liz what defines The Chicago Academy for the Arts, and her answer is simple, yet profound: This is a place where students want to be, and where they are truly known.

In classrooms, studios, and rehearsal spaces, students are encouraged to show up fully as themselves. They are challenged not only to grow as artists, but to embrace vulnerability in their learning — both creatively and academically.

Liz has spent her career ensuring that every student has the support they need to meet those challenges. Through Learning Resources, she has helped students navigate obstacles, build confidence, and discover their own capacity for growth.

Because when a student learns they can master something difficult in their art, something powerful happens: they begin to believe they can do difficult things anywhere.

The Heart That Hasn’t Changed

Over twenty years, much has evolved at The Academy: programs have expanded, facilities have grown, and new generations of artists have stepped into our halls.

But according to Liz, the heart of this place has remained unchanged.

It’s a belief that meaningful work matters. That students deserve to be seen and supported. And that art is not an extracurricular luxury; it is essential.

In a world moving rapidly through technological change, Liz sees The Academy’s role more clearly than ever: to affirm the value of human creativity, connection, and expression.

As long as that belief endures, she says, The Academy will continue to be true to itself.

Beyond the School Day

While students may see Liz as a steady and supportive presence throughout the school day, there’s more to her routine than meets the eye.

She starts each morning at 5:15 a.m. with a full hour-long walk — preparing herself for the energy and pace of a typical day at The Academy. And yes, in a true testament to her all-in approach to community, she’ll even tell you that sometimes the job includes washing dishes.

Outside of school, Liz finds inspiration in her summer garden and in travel, especially anywhere with mountains, water, or ideally both. Her current creative influences span disciplines, from textile artist Bisa Butler to musicians like Phosphorescent, as well as writers and filmmakers including Claire Keegan, Jessie Buckley, and Clint Bentley’s Train Dreams.

And in a detail students might not expect: Liz holds an Irish passport and dreams of one day spending time in Ireland, raising Irish donkeys in retirement.

A Life in Service of Young Artists

When asked what she hopes the community knows, Liz keeps it simple: Spending her days at The Academy has been one of the great pleasures of her life.

For twenty years, Elizabeth Cunningham has been a steady presence, a fierce advocate, and a compassionate leader within The Chicago Academy for the Arts. She has guided students through challenges, celebrated their breakthroughs, and helped shape a community where young artists can thrive — not just as performers or creators, but as confident, capable individuals.

And while countless things have changed over the years, one thing is certain: Because of Liz, The Academy’s heart beats stronger than ever.

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