Staszak Outstanding Teacher of the Year Award winner Longfellow art teacher Jenny Raia (second from right) with Luke Staszak, Longfellow School Asst. Principal Torri Morris Oak Park Educaton Network Executive Director Latonia Baker and Longfellow Principal Amy Jefferson on Wednesday April 15, 2026 | Todd Bannor

Longfellow School art teacher Jenny Raia has loved art for as long as she can remember. When she was a child growing up in Elmhurst attending a Catholic grade school her school did not offer an art class so she gathered some classmates and friends before school and created one of her own. She has taught art at Longfellow for 22 years and her passion and dedication was recognized last week when Raia received the Staszak Educator of the Year award handed out annually by the Oak Park Education Foundation. 

Raia was recognized on April 15 in the Longfellow gym in front of the entire school and on April 19 at the foundation’s annual Spring Open House held at Percy Julian Middle School. She received a $1,000 check as the winner of the award. 

“It was exciting and it feels good to be recognized,” Raia told Wednesday Journal. 

Raia said she will use the $1,000 to help pay for an art education trip she makes annually to New York City. 

For a few years after graduating with a bachelor’s of fine arts in painting from Metropolitan State University of Denver Raia was a professional artist while holding down a number of other jobs, some art related and some not, and doing a lot of volunteering. An outgoing person, she wasn’t crazy about the long hours alone in a studio making art and eventually she decided to become a teacher. 

“I felt like I didn’t have enough to say as an artist but I loved making things,” Raia said. 

Longfellow School teacher Jenny Raia (center) with Longfellow Assistant Principal Torri Morris enters the gymnasium to receive her Staszak Outstanding Teacher of the Year Award on Wednesday April 15, 2026 | Todd Bannor

So she went back to school and got a masters degree in teaching from Columbia College. Newly married and living in Oak Park she decided that she wanted to teach in Oak Park. 

“I wanted to have a family in Oak Park and I wanted to be able to walk to work,” Raia recalled. 

After student teaching at Mann School and Oak Park and River Forest High School she was hired to teach art at Longfellow School and that’s where she’s been for the past 22 years. Raia loves teaching in a community that values art. 

“I’m just really grateful to be an art teacher and I can’t be at a better place to be an art teacher,” Raia said. 

Raia comes up with fun projects for her students at Longfellow who have art once a week. She also focuses on equity and inclusion while working with kids who have a wide range of artistic ability. 

“It’s not just about making art projects or just creating crafts, we’re trying to make better citizens,” Raia said. 

Luke Staszak and Latonia Baker of the Oak Park Education Network greet art teacher Jenny Raia, winner of the Staszak Outstanding Educator of the Year Award at Longfellow School on Wednesday April 15, 2026 | Todd Bannor

A few students spoke at the Longfellow assembly honoring Raia. 

“She’s a really great teacher with an awesome personality, but one thing that I really like is how helpful she is,” one girl said. “And it’s not just me that she helps, she answers questions from dozens of students in dozens of classes. She’s also always great at planning the most fun projects. She has a way turning all our classes into the best day of the week.” 

A boy also praised Raia. 

“You have one of the biggest hearts I’ve ever met in my life and I’m happy that you are my art teacher,” the boy said. 

Longfellow Principal Amy Jefferson praised Raia in an interview saying that Raia is a “super creative” teacher. 

“She has taken on many opportunities to expand the program for art for our students, whether that’s having former students come back who are now artists to do murals for us or participate in lessons for us but she also has participated in the professional learning opportunities for adults as well,” Jefferson said. 

As art department chairperson in District 97 Raia, who is studying for her PhD at Northern Illinois University, plans professional development for the art teachers in District 97. She treasures her colleagues. 

“We have 15 art teachers in District 97 and every single one of them could have gotten this award,” Raia said. 

Raia loves teaching art. 

“You don’t show up every day to get an accolade, you show up because it’s important and it’s your calling,” Raia said. “If you’re an art teacher and you’re bored at your job that’s on you.” 

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