Featured Events
All Saints’ Day of Giving
Regarding modern man, G.K. Chesterton once wrote: “He has always lost his way; but now he has lost his address.”
At Chesterton Academy of The Holy Family, we know our true address to be in Heaven. We guide our students toward this ultimate home through the truths of the Catholic faith and by bringing them into conversation with the greatest thinkers and Saints. This prepares them to confront the biggest questions and challenges of the modern world, with the friendliness to bring others along for the journey.
Our joyfully Catholic, classical education is an antidote to the aimlessness pervading our culture. Your support is crucial to the success of our work. On November 1, we invite you to participate in Chesterton Academy of The Holy Family’s annual All Saints’ Day of Giving.
Your gift will support our Saints Fund, providing critically needed dollars for the operation of the school, including helping to recruit and retain faithful Catholic faculty, allowing for daily Mass, and providing meaningful faith formation and student life opportunities.
MAKE YOUR GIFT TODAY OR ON NOVEMBER 1 and help us meet and exceed our $50,000 goal.
Please give generously and support our future saints!
Open House + Odyssey Day
We’ve designed one day to give prospective parents and students two ways to experience our school.
Parents will have the opportunity to join us for Mass, tour the school, meet our school leaders, and learn about what makes a Chesterton education distinctive. Our parent portion of the day will conclude after Mass at 10:15 AM.
Your sons and daughters will experience a day as Chesterton students. They will participate in their own classes. Additionally, they will join our current students for lunch and Lyceum, our daily time for recreation and friendship. Your students’ day will conclude at 12:30 PM.
Parents can enjoy refreshments and snacks. A free lunch will be provided to our visiting students.
Choosing a high school takes more than just reading about it. Come and meet our faculty and staff, experience the classroom, and see life at Chesterton. Join us and discover Chesterton for yourself.
Anne of Green Gables
“Anne of Green Gables,” adapted by Joseph Robinette from the novel by L.M. Montgomery, will be performed by the Junior class.
Marilla Cuthbert and her brother Matthew live in the farmlands of Prince Edward Island. The aging couple requests an orphan boy to help work their farm. Instead, they are mistakenly sent the high-spirited redhead named Anne Shirley. Knowing they are ill-equipped to raise a young girl who is incapable of properly helping on their farm, Marilla attempts to send Anne back to the orphanage. With Matthew lobbying to keep Anne and despite warnings from a neighbor, Marilla ultimately agrees to let her stay at Green Gables. Almost immediately, Marilla’s fears come to pass as Anne insults Marilla's best friend, smacks the school's prize pupil with a slate, inadvertently gets her best friend, Diana, drunk on cherry cordial, and ends up with a broken leg after fulfilling a dare. However, despite these and other trying situations, Anne’s bright, charming, and resourceful personality, along with her irresistible imagination, helps her win the deep love and admiration of the whole town and especially Marilla and Matthew, who admit she is the best thing that ever happened to them and a true gift from God.
Anne of Green Gables
“Anne of Green Gables,” adapted by Joseph Robinette from the novel by L.M. Montgomery, will be performed by the Junior class.
Marilla Cuthbert and her brother Matthew live in the farmlands of Prince Edward Island. The aging couple requests an orphan boy to help work their farm. Instead, they are mistakenly sent the high-spirited redhead named Anne Shirley. Knowing they are ill-equipped to raise a young girl who is incapable of properly helping on their farm, Marilla attempts to send Anne back to the orphanage. With Matthew lobbying to keep Anne and despite warnings from a neighbor, Marilla ultimately agrees to let her stay at Green Gables. Almost immediately, Marilla’s fears come to pass as Anne insults Marilla's best friend, smacks the school's prize pupil with a slate, inadvertently gets her best friend, Diana, drunk on cherry cordial, and ends up with a broken leg after fulfilling a dare. However, despite these and other trying situations, Anne’s bright, charming, and resourceful personality, along with her irresistible imagination, helps her win the deep love and admiration of the whole town and especially Marilla and Matthew, who admit she is the best thing that ever happened to them and a true gift from God.
Anne of Green Gables
“Anne of Green Gables,” adapted by Joseph Robinette from the novel by L.M. Montgomery, will be performed by the Junior class.
Marilla Cuthbert and her brother Matthew live in the farmlands of Prince Edward Island. The aging couple requests an orphan boy to help work their farm. Instead, they are mistakenly sent the high-spirited redhead named Anne Shirley. Knowing they are ill-equipped to raise a young girl who is incapable of properly helping on their farm, Marilla attempts to send Anne back to the orphanage. With Matthew lobbying to keep Anne and despite warnings from a neighbor, Marilla ultimately agrees to let her stay at Green Gables. Almost immediately, Marilla’s fears come to pass as Anne insults Marilla's best friend, smacks the school's prize pupil with a slate, inadvertently gets her best friend, Diana, drunk on cherry cordial, and ends up with a broken leg after fulfilling a dare. However, despite these and other trying situations, Anne’s bright, charming, and resourceful personality, along with her irresistible imagination, helps her win the deep love and admiration of the whole town and especially Marilla and Matthew, who admit she is the best thing that ever happened to them and a true gift from God.
Anne of Green Gables
“Anne of Green Gables,” adapted by Joseph Robinette from the novel by L.M. Montgomery, will be performed by the Junior class.
Marilla Cuthbert and her brother Matthew live in the farmlands of Prince Edward Island. The aging couple requests an orphan boy to help work their farm. Instead, they are mistakenly sent the high-spirited redhead named Anne Shirley. Knowing they are ill-equipped to raise a young girl who is incapable of properly helping on their farm, Marilla attempts to send Anne back to the orphanage. With Matthew lobbying to keep Anne and despite warnings from a neighbor, Marilla ultimately agrees to let her stay at Green Gables. Almost immediately, Marilla’s fears come to pass as Anne insults Marilla's best friend, smacks the school's prize pupil with a slate, inadvertently gets her best friend, Diana, drunk on cherry cordial, and ends up with a broken leg after fulfilling a dare. However, despite these and other trying situations, Anne’s bright, charming, and resourceful personality, along with her irresistible imagination, helps her win the deep love and admiration of the whole town and especially Marilla and Matthew, who admit she is the best thing that ever happened to them and a true gift from God.
Lessons and Carols
Save the Date! The time is tentative.
More details coming later this fall.
Fleur-de-Lis Gala
The Fleur-de-Lis Gala is an annual event hosted by Chesterton Academy of the Holy Family. The Gala is an excellent opportunity to enjoy an evening with the community.
The evening will feature choir performances, dancing, music, student testimonials, a silent auction, and so much more.
Please stay tuned for further details and updates.
Grandparents Day
A school is a work of generations, and grandparents have often been among our quietest and most faithful supporters. In that vein, we warmly invite the grandparents of our Saints families to join us for Grandparents Day.
8:00 AM All-school Mass (optional)
9:00 AM Breakfast
9:25 AM Discussion led by Kevin Middlesworth about "How Wonder Leads You to Christ"
10:30 AM Event concludes
To RSVP please email tanya.cummins@cathf.com
We would be glad for them to see what their support has built and to hear the hopeful news of what lies ahead. Saints families, please kindly extend this invitation to them, and we hope to see them at the event!
Open House + Odyssey Day
We’ve designed one day to give prospective parents and students two ways to experience our school.
Parents will have the opportunity to join us for Mass, tour the school, meet our school leaders, and learn about what makes a Chesterton education distinctive. Our parent portion of the day will conclude after Mass at 10:15 AM.
Your sons and daughters will experience a day as Chesterton students. They will participate in their own classes. Additionally, they will join our current students for lunch and Lyceum, our daily time for recreation and friendship. Your students’ day will conclude at 12:30 PM.
Parents can enjoy refreshments and snacks. A free lunch will be provided to our visiting students.
Choosing a high school takes more than just reading about it. Come and meet our faculty and staff, experience the classroom, and see life at Chesterton. Join us and discover Chesterton for yourself.
Senior Drama
Senior Drama Presents: A Midsummer Night’s Dream by William Shakespeare - Tittania Cast
Senior Drama
Senior Drama Presents: A Midsummer Night’s Dream by William Shakespeare - Tittania Cast
Senior Drama
Senior Drama Presents: A Midsummer Night’s Dream by William Shakespeare - Tittania Cast
Senior Drama
Senior Drama Presents: A Midsummer Night’s Dream by William Shakespeare - Tittania Cast
Fleur-de-Lis Gala
Join friends and benefactors for an elegant evening of music and merriment in support of Chesterton Academy of The Holy Family. This signature event—our school’s primary fundraiser—welcomes more than 1,000 guests and brings together our board of directors, benefactors, families, and friends in joyful celebration of our mission. The evening is open to guests age 21 and older, with a special invitation extended to prospective 8th-grade students, young alumni, and their parents to join us.
When: Friday, January 30, 2026, with doors opening and the cocktail reception beginning at 5:30 PM, dinner at 7:00 PM, the silent auction closing at 9:00 PM, and live band and dancing from 9:30–11:00 PM; Location: Drury Lane, Oakbrook Terrace, Illinois.
Chesterton Supper Club for Parents, Alumni Parents, Board Members & Faculty/Staff
The Supper Club is for Parents, Alumni Parents, Faculty, Staff, and Board Members. In October, we welcome a guest speaker to speak on AI and your faith! Signup via The Chesterton Weekly Newsletter. Reservations required.
Class of 2029 Family Summer Picnic
Class of 2029 Summer Picnic
We’re excited to welcome the Class of 2029 and their families to a fun summer picnic! Join us for a casual evening of community and connection. Wear your freshman t-shirt and bring your own picnic. We can’t wait to see you and your entire family!
Fore! All the Marbles
Celebrate Chesterton Academy of The Holy Family at our 2nd annual golf outing, Fore! All the Marbles. It promises to be a memorable day filled with fun and camaraderie on the links as we raise scholarship funds for our students!.
Our four person scramble will begin with a shotgun start at 1:00pm. This event is open to golfers of any age, with options to register as an individual or a foursome. Minors must be accompanied by an adult.
Our 2025 Fore! All the Marbles golf outing presents another occasion to pay tribute to the cherished memory of Andrew Karas, a beloved Chesterton dad. Andy, the school's first golf coach, was renowned for his witty sense of humor, his unwavering faith, and his dedication as a loving husband, father, and grandfather. Alongside his wife, Laura, he was a committed volunteer at Chesterton Academy of The Holy Family.
All net proceeds generated from Fore! All the Marbles will be directed toward the G.K. and Frances Chesterton Scholarship Fund in Andy Karas' name.
