Classical High School Teacher - Lisle, IL Society of Gilbert Keith Chesterton

Join us in shaping the future of Catholic classical education! Join a Joyfully Catholic, Classical High School Forming Saints and Scholars.

We are expanding as we enter our 12th school year, and we are accepting applications for the 2026-2027 academic year! We are looking for passionate and talented educators to join our dynamic faculty in the following subject areas:

• Humanities, including History, Latin and Literature

• Math & Science
  
  Special Qualities & Characteristics
  • Passionate about the mission of Chesterton Academy and its three pillars: spiritual, intellectual, and virtue formation
  • Deep appreciation for the Catholic faith and a commitment to the teachings of the Church
  • Practicing Catholic willing to take an Oath of Fidelity to the Magisterium of the Roman Catholic Church
  • Strong initiative and desire to work in a highly collaborative environment
  • Excellent rapport with parents, students, and fellow staff members
  
  Compensation & Benefits
  • Competitive salary, commensurate with experience
  • 401(k) retirement savings plan, Health Insurance Stipend
  • Generous paid time off, including approximately 26 PTO days for school holidays
  • Paid sick leave included in PTO policy
  • Annual professional development opportunity at the Chesterton Schools Network Summit Conference
  • Additional stipends available for coaching and extracurricular responsibilities
  
  If you feel called to teach truth, goodness, and beauty, we invite you to apply today and join a school dedicated to forming joyful leaders, faithful Catholics, and thoughtful scholars. This is more than a job-it's a vocation. Chesterton Academy of The Holy Family is a religious 501(c)3.
  
  Apply today online at: www.chestertonacademyoftheholyfamily.com/careers

• Deliver engaging lessons to students, follow the Chesterton Academy course curriculum with fidelity, lesson plans are completed for you by the Chesterton Schools Network (CSN)

• Assess, record, and maintain student progress using the school's online grading system

• Provide written assessments, reports, and references for individual students

• Collaborate with the Department, Dean of Curriculum & Instruction, Head of School on curriculum

• Participate in school in-service education and professional development sessions

• Attend staff meetings, group meetings, and other school-related gatherings

• Supervise students outside the classroom, including during lunch, at after-school events, and on school retreats

• Bachelor's or Master's degree in Liberal Arts, History, Literature, Languages, Mathematics, or Science

• New graduates with a deep love for Catholic classical education are encouraged to apply

• Passionate about teaching subject matter; patient and kind with students

• Committed to embracing the school's mission and vision and fostering a joyful atmosphere

• Eagerness to participate fully in the life of the school, including daily Mass, the House system, and community events

Chesterton Academy of The Holy Family is a joyfully Catholic high school offering a classical liberal arts education rooted in the Catholic intellectual tradition. As a member of the Chesterton Schools Network, the Academy forms students in faith, reason, and virtue, fostering a love for truth, goodness, and beauty. Entering its 12th academic year in 2026–2027, Chesterton Academy of The Holy Family serves families in Lisle, Illinois, near Chicago and Naperville. Our incarnational school culture is centered on daily Mass, strong faculty-student relationships, and an integrated curriculum that forms the whole person—mind, body, and soul. Affiliated with the Diocese of Joliet, the Academy is proud to contribute to the renewal of Catholic classical high school education.