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Student Life



Chesterton Academy is a member of WIAA and also participates in some DASH programs and co-ops with other schools. 



Fall Sports

  • Girls' Volleyball
  • Boys' Volleyball
  • Cross Country(co-op)
  • Boys' Football (SWCHA)

Winter Sports

  • Boys' Basketball
  • Girls' Basketball
  • Fencing Club
  • Soccer Club (Boys/Girls/Co-ed)
  • Ski/Snowboarding Club

Spring Sports

  • Boys' Baseball
  • Boys' Track & Field
  • Girls' Track & Field
  • Golf (Co-ed)

Clubs & Activities


Clubs & Activities

ACT/SAT Review Club
Art Club
FTC Robotics Club
Math Club
Swing/Ballroom Dance
Yearbook Club


Folk Music Club

Faith & Service

Ambassador Club
Pro-Life Club

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 a senior and junior prefect and a faculty advisor.

Learn More →


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  • Daily Mass The Eucharist is "the source and summit of the Christian life." For in the blessed Eucharist is contained the whole spiritual good of the Church, namely Christ himself, our Pasch. CCC 1324 For this reason, every school day begins with Mass.
  • Faith at the Center  The faith is the central reality from which all academic disciplines flow and derive their meaning. Faith is at the core of our academic program.  All subjects we teach through lens of the Church.  This makes our school unique. Religion at CA is not merely one academic subject among many. 
  • Retreats and Prayer Students pray the Morning Offering and the Angelus. Retreats are held at Holy Hill and Our Lady of Good Help
  • Unique Calling Each person has a unique and unrepeatable gift. Students are prepared for life which means finding their vocation and discerning their calling for their lives. 
  • Building up the Kingdom of God … To use the skills they acquire at CA in faith, hope, and charity to build the Kingdom of God in this life and be with Him in everlasting happiness in the next.
 There is a whole truth of things and in knowing and speaking it we are happy.
— G.K. Chesterton


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Holy Hill & Our Lady of Good Help

Every year, Chesterton students begin the year with a pilgrimage to the National Shrine of Mary Help of Christians at Holy Hill. They also enrich their spiritual lives with trips to the Shrine of Our Lady of Good Help in Champion, as well as other local field trips.

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Chicago March for Life

Chesterton Academy of Milwaukee students join our friends to the south, Chesterton Academy of the Holy Family and Chesterton Academy of the Sacred Heart, in Chicago on the anniversary of Roe v. Wade, giving a voice to the voiceless. 

Next March for Life Pilgrimage - January 2019
Chesterton Academy will again travel to Chicago for the March for Life with other young people from the Milwaukee area and throughout the mid-west.