Herbert T. Flentye

Herbert Thomas Flentye, Sr., 81, of Chicago, Illinois passed away peacefully on August 12, 2025, surrounded by his family. Born on October 25, 1943, in Chicago, Illinois to the late Herbert and Florence Flentye, Herb lived a life defined by humility, strength, and an unwavering love for God, family and country. He was a man who didn’t seek the spotlight but whose presence grounded everyone around him, always willing to give the gift of time. Whether offering a listening ear, a “grandpa joke”, or the quiet of his company, he had a way of making people feel safe and seen.

At the center of his world was his beloved wife, Bernadene. Together over their 59 years they raised a family that became his great pride and joy—children and grandchildren who knew they were deeply loved.

Herb was a lifelong sports fan, often found with the Cubs, Bears, or Bulls on in the background. But even more than that, he was THE biggest fan of watching his five grandchildren on the field or court —always there quietly on the sidelines.

He found peace at the lake, casting a line, planting flowers, taking care of his dogs, and making memories with his family that will be cherished forever. He taught lessons in presence through conversation and in patience, humility and resilience through the way he lived.

Herb was preceded in death by his parents, his sisters, Lois White (Bill) and Grace Smith (Chuck), and his brother, Tom Bush. He is survived by his loving wife, Bernadene, his daughters, Lynn Flentye and Kristen Kennedy (Mike), his son, Herb Flentye (Laura), his cherished grandchildren: Kaley Flentye, Austin Kennedy, Megan Flentye, Ryan Flentye, and Kaitlyn Kennedy, and his many beloved nieces and nephews. He was a wonderful, kind, caring, and incredible man, a quiet rock, and the heart of his family. He will be deeply missed.

A wake will be held on Friday, August 15, 2025 from 4-8pm at Rago Brothers Funeral Home at 7751 W. Irving Park Rd. in Chicago. A Funeral Mass will be held at St. Eugene’s Church at 7958 W. Foster in Chicago at 10:30am on Saturday, August 16, 2025. In lieu of flowers, the family asks that donations be made to St. Judes, Shriners Children’s Hospital, and Misericordia in Herb Flentye’s memory.