Featured Events
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.
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.
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.
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.
Open House April
Join us for Mass at 8 AM, Presentation at 9 AM, Visit Classes Afterwards. We want to show you the Chesterton Difference. So come check out Philosophy, Literature, Chemistry and so much more. Coffee and Light Snacks available after Mass!
