Winifred Jane Sipchen, née Callery, 94, longtime resident of Glenview, passed away peacefully on December 13, 2025 at Norwood Crossing in Chicago. Beloved wife of Jim. Devoted mother to Jim, jr. (Rhonda) and David (Julie). Cherished grandmother of Henry, John Patrick, Claudia, Nora, Sarah, Kate and Matthew. Dear sister of the late Robert (Ann), Mary Alice (the late Robert Stanley "Tub") Thomas and John (Beatrice). Adored daughter of the late Raymond and Mary Agnes, née Welsh. Dear aunt to three generations of nieces and nephews.
Win was raised in the small town of
Princeville, Illinois, where she was the youngest of four children in a home filled with love, faith, and a strong connection to and pride in her Irish-American heritage. She fondly recalled stories of her carefree childhood, days as a University of Illinois co-ed, and life in 1950's Washington, D.C., as a young, independent woman working in the U.S. intelligence community. A mid-westerner at heart, Win returned to Illinois while still in her 20's when she was offered a position as an editor for a small professional publication and eventually moved on to the Chicago Sun-Times, where she met Jim Sipchen in the advertising department. After noticing that their two, sporty roadsters were a strikingly good match, they decided they must be too and were married at St. Michael's on December 17, 1966. This year would have marked their 59th anniversary.
In their years of marriage, Win and Jim marked many milestones. They were newlyweds in Oak Park and within a couple of years had started a family. In 1968, came Jim, and shortly after with David's birth, Win and Jim moved to their home in Glenview where they would live for over 45 years and create countless happy memories. Win was a talented cook and would create everything from her Irish corned beef and cabbage with soda bread for St. Pat's, to roast lamb for Easter feasts, and absolutely delicious chili or enchiladas on freezing winter days. She would often be interrupted by her children and drop everything to play in or referee pick-up basketball games on their patio court or create countless professional or college football, basketball, or baseball logos for homemade uniforms to be donned for backyard games.
Win was a wonderful grandmother to her seven grandchildren, babysitting at a moment's notice-often times arriving with a casserole for the next night's dinner, attending sports events, recitals, dance competitions, concerts, plays, art exhibitions, and always making sure her grandchildren knew how special they were to her. And Win was a wonderful and welcoming mother-in-law, who once shared the sage advice given her by a dear friend, that the primary responsibility of the mother-of-the-groom is to wear beige. This was just one of Win's many hilariously funny, and often true, sayings collected along the way or coined herself which always made everyone feel welcome, comfortable, and at ease, including her daugthers-in-law, who quickly knew they had found a good friend and role model. Win also was never one to impolitely give advice or to correct a mistake. Rather, she would muse, "I wonder what people do about……?" With her gentle delivery no offense was ever taken, but her message was always received. Like magic.
Finally, Win was an athlete, and her favorite sport was golf which she only began to play regularly after her youngest son went away to college. She became a strong player and especially loved the short game. Win loved to talk about and play golf with her grandchildren and was very excited to hear about any of them who might take up the sport she loved so much. She very much enjoyed her ladies' leagues in Glenview and played until she was 90. She considered herself a golfer until the end.
Win was a dear, loyal, and loving friend to so many throughout her life. She will be missed by her many friends and family. She is at peace.
December 23, 2025, memorial visitation will be held from 9:15am until the time of the funeral Mass at 10am at Our Lady of Perpetual Help Catholic Church, 1775 Grove St,
Glenview, IL 60025. Livestream is available here. Private inurnment. More info 847-901-4012.
In lieu of flowers, please send donations to :
The Cause for the Beatification and Canonization of Fulton Sheen
Archbishop Fulton J. Sheen Foundation
419 NE Madison Ave. Peoria, IL 61603
[email protected]