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Student Life




We are an IHSA school and competed this year in the Metro Prep conference in boys and girls basketball, soccer, and volleyball.  In spring of 2019, Chesterton Academy had its first men’s rugby season. Several other athletic clubs are also offered for our students.



Fall Sports

Winter Sports

  • Men’s Basketball

  • Women’s Basketball

Spring Sports

  • Men’s Rugby

  • Women’s Soccer


Student Activities



Frassati Fellowship
Literary Journal
Yearbook Club


Chamber Choir (audition-based)
Men’s Schola and Women’s Schola

Faith & Service

Cultura Vitae, Culture of Life

House System

Chesterton Academy’s House System is drawn from the 1,000 year-old tradition of Christian education exemplified in the colleges at Oxford and Cambridge. The Houses provide real, tangible community within the larger school, giving students the opportunity to take ownership, fulfill the call to leadership, and to cultivate the ideal conditions for virtue. Each House has two senior and two junior prefects, two faculty advisers, and several parent liasons.

Learn More →


Rome and Assisi

Our 2019 pilgrimage took us to all the major churches in Rome, Orvieto, and Assisi in just under two weeks. We walked the paths of pilgrims, prayed at the tombs of the martyrs, and enjoyed being steeped in Italian culture. Accompanied by our chaplain Fr. Michael Kearney and our tour guide Joe Long of ProRome, this pilgrimage helped our students grow in faith and deepen their friendships—all while learning about the history of our Church and the Eternal City.

Please feel free to view our photo album from the trip, as well as videos of our students singing in a number of the beautiful churches we visited.

Next Pilgrimage to Rome and Assisi - March 2021
Chesterton Academy freshmen, sophomores, and juniors: stay tuned for more information in fall 2019.


National March for Life and March for Life Chicago

Chesterton Academy students join hundreds of thousands of peaceful protesters in Washington, D.C. on the anniversary of Roe v. Wade giving a voice to the voiceless. 

Next March for Life DC Pilgrimage - January 2020
Chesterton Academy of the Holy Family will again travel with fellow high school students from Illinois and around the country. In addition to the national rally, we will attend the Students for Life conference.