In 2007, Tom Bengtson and Dale Ahlquist co-founded the first Chesterton Academy high school in Minneapolis, Minnesota. Each had young families and were seeking an alternative to the existing high school options available to them. The two men had a simple mission: to offer a classical, integrated high school education that was faithful to the Catholic Church and affordable for families of average means. Looking to G.K. Chesterton as the model for a complete thinker and modern defender of the faith, they named the school Chesterton Academy. Inspired by Pope Saint John Paul II, they took as their motto Cultura Vitae, the culture of life.

Today, there are 27 high schools operating as part of the Chesterton Schools Network in the U.S. and Canada, with two dozen new schools slated to open in 2021 and 2022, including the Chesterton Academy of the Incarnation.