Dorothy Sybert

June 13, 1940 – December 6, 2025

Dorothy Sybert, beloved wife, mother, grandmother, great-grandmother, aunt, and cousin, passed away peacefully at home in Northbrook, Illinois, on December 6, 2025, at the age of 85, finally resting after a long and courageous battle with cancer.

Born June 13, 1940, in Chicago to Gladon and Dorothy Gregory (Langham), she lived her life with fierce determination, a joyful unbreakable heart, and the sweetest of souls. She was the person who quietly helped everyone—family, friends, even strangers—always going out of her way to make life brighter for those around her. Years earlier she had faced cancer and, through sheer will and extraordinary medical care, defeated it—gifting herself and everyone who loved her many more vibrant, joy-filled years than anyone dared hope. In the end, the lasting effects of those powerful treatments simply asked too much of even her remarkable strength.

A proud Chicagoan through and through, Dorothy met the love of her life, Milton T. Sybert, while working as a spirited secretary at Union Tank Car Company. What began with shared glances across a Chicago office blossomed into more than sixty years of unwavering partnership and profound love. Together they raised a family, built a thriving business (where Dorothy considered the employees of C.J. Anderson & Company her second family), created a lifetime of memories at their beloved lakehouse in Northern Wisconsin, and, in retirement, traveled the world—camera in one hand, Milt’s hand in the other—capturing every destination they had ever dreamed of seeing.

Dorothy’s heart was wide open to her many cousins scattered across Northern Wisconsin and Illinois and to a cherished circle of lifelong friends. Her passions lit up her days: a formidable competitor on tennis courts, later on pickleball and golf courses; a devoted reader; and, from 1990 to 2008, a proud and accomplished member of the Melodeers Chorus and various quartets, helping the chorus win six international championships—titles she treasured deeply.

In their later years, Dorothy and Milt made their home at Northshore Place in Northbrook, where they formed deep, unexpected, and lasting friendships with residents and staff alike. The compassionate team there became true extended family, wrapping them in care and comfort during their final chapters.

Dorothy was the devoted mother of Alan Sybert (Jane) and Thomas Sybert (Tiffany) and a loving mother-in-law to Mary Lou Sybert. She is survived by her brother Richard Gregory (Doree) and his family, including her niece and several nephews; many adored cousins across Northern Wisconsin and Illinois; her grandchildren Zack, Owen, Quinn, Stephanie, Kelsey, Lucas, Samantha (Ben Hurd), and Jon (Jill); and her great-grandchildren Nolan, Nathan, Isabel, Henrik, Britta, and Benji.

She was preceded in death by her beloved husband Milton, who passed on April 29, 2025; her stepson Steve Sybert; and her parents.

A private family memorial will celebrate Dorothy’s extraordinary life and her joyful reunion with Milt. In lieu of flowers, the family asks that you perform a loving random act of kindness in memory of Dorothy and Milton Sybert.

Dorothy leaves behind a legacy of fierce determination, boundless love for her family, and a spirit that carried her from championship stages to tennis courts to sunsets all over the world. Now free from pain, she and Milt are together again—watching sunsets at their lakehouse, sharing a Manhattan with two cherries, and smiling down on the beautiful family they built.