Careers at Chesterton

Recently Posted Positions:

We are accepting applications for faculty and staff positions for the 2025 - 2026 academic year. Click below to start an application.

Chesterton Academy of The Holy Family, founded in 2015, is the fourth school in the Chesterton Schools Network.

Under the patronage of G.K. Chesterton and in partnership with families and the Church, the mission of the Chesterton Schools Network is to foster a Culture of Life by forming a new generation of joyful leaders and saints, educated in the classical tradition and grounded in the truths of the Catholic faith.

About Chesterton Academy of The Holy Family

  • Chesterton Academy of The Holy Family (CATHF) is a joyful, faith-based Catholic high school committed to delivering a classical liberal arts education that fosters intellectual, moral, and spiritual growth. Established in 2015 in Downers Grove, IL and since 2019 located in Lisle, IL, we proudly belong to the Chesterton Schools Network (CSN), dedicated to the joyful pursuit of truth, goodness, and beauty. As we enter the 2024-2025 academic year, we celebrate our 10th anniversary as the fourth CSN school to open. The network will span to over 65 schools worldwide, unified by a shared curriculum and branding set by the CSN. As a member, we follow the curriculum and branding guidelines set forth by the Chesterton Schools Network. Read more about our curriculum here.

  • As a classical high school, we value versatility and a passion for teaching across various disciplines. Beyond classroom instruction, you’ll play an essential role in fostering a joyful, virtuous environment through advising, monitoring, mentoring club meetings, and contributing to a positive culture. Daily Mass attendance is required, along with participation in events outside the school day—such as CV events, sports, concerts, plays, meetings, and parent gatherings—to help build a vibrant culture of life. Engaging in community life is central to your role at Chesterton Academy of The Holy Family, where we aim to educate the whole person, body and soul united. We encourage our staff to draw inspiration from Saint John Bosco, modeling the behaviors we wish to cultivate in our students.

  • Chesterton Academy of The Holy Family hires employees and admits students of any race, color, national origin, or ethnic origin to all the rights, privileges, programs, and activities generally accorded or made available to students and employees at the school. It does not discriminate based on race, color, national origin, or ethnic origin in its educational policies, administrative policies, admission policies, scholarship, and athletic and other school-administered programs.

Accepting Faculty and Coaching applications for the 2024-25 academic year:

Latin and Italian Faculty
Ladies and Men’s Soccer, Volleyball and Basketball,
Men’s Rugby and Golf

To apply for a position at Chesterton Academy of The Holy Family:

Applications for all positions can be submitted on the employment application form. We will not accept applications sent to us via email.

Interested candidates are asked to reflect on the Chesterton Academy of The Holy Family website before applying for a position. If, after prayerful consideration, an applicant believes he or she can support and embrace the mission of the school, applicants are to complete and submit the following via this link:

  • A completed candidate questionnaire, cover letter expressing their position of interest, current resume, essay and references.

  • Provide a maximum one-page typed response to the following: “Having reflected on Chesterton Academy of The Holy Family’s mission, which articulates our identity as a Catholic school and then explain in what specific ways you anticipate supporting and advancing our school’s mission.”

  • List of three to five professional references with name, relationship, phone number and email address (references will not be contacted without the candidate’s permission).

Please be sure to use only the employment application form to apply for a position. If there is a need and a fit, we’ll reach out to you for an interview. We are unable to respond to emails and phone calls about the status of an application.