Sheila Reynolds Trainor

Sheila Reynolds Trainor, 70, of Oak Park, died on Oct. 21, 2023. Born in Chicago on Nov. 22, 1952 — along with her triplet sisters, Martha and Regina — to Paul and Sheila (Taaffe) Reynolds, she grew up in the big home on Longwood Drive in the Beverly neighborhood with room enough to raise a large Irish-Catholic family of 14, with the odd foster child and foreign exchange student tossed in for good measure. A spirited lass, she had a radiant smile. At one point in her youth, she was even a member of the local chapter of Up with People. 

She accumulated her Catholic education at St. Barnabas Elementary, Mother McAuley High School, St. Xavier University (where she met her best friend, Margaret Stipley Cherene), and ultimately graduated from Loyola University Chicago with a degree in primary education. A year studying abroad at the Loyola Rome Center was one of the great adventures of her life. Another was the following year when she accompanied her brother Chris to Chile for the wedding of a former foreign exchange student just after Pinochet’s bloody coup.

She married Ken Trainor in 1978 and in 1984, their son Dylan was born. They lived in Rogers Park; Ft. Collins, Colorado (where she earned a master’s degree in education at Colorado State University); Mt. Pleasant, Michigan (where she ran the Central Michigan University daycare program); and finally settled in Oak Park. She taught for more than a decade at Beye and Whittier schools in Oak Park’s District 97, learning all she needed to know teaching kindergarten — and other primary grades. After the onset of multiple sclerosis limited her mobility, she continued to tutor and teach Spanish (fortified in Cuernavaca, Mexico in 1975 during an immersive language arts program, plus a side trip to Peru). 

As a primary school educator, she was a natural. Children were drawn to her and she made them feel safe and cared about.

She loved horses, coffee, reading, dogs and cats, traveling, nature, watching Antiques Road Show and Jeopardy!, reminiscing about her childhood, spending time with her grandchildren, spending summers with family at Palisades Park in Michigan, visiting the Ontario fishing lodge of her friend Joanne Mortimer as teenagers, and later with the Cherene family at Lake Lawn in Wisconsin, skiing at Keystone Resort in Colorado, playing tennis (at one junior tournament she ran into Arthur Ashe, literally, in a stairwell), writing children’s stories, photography, and creating photo memory books. She was the undisputed champion of Trivial Pursuit at the Brookdale facility where she lived.  

Sheila is survived by her son, Dylan (Emily); her daughter-in-law Kristen; her grandchildren, Tyler, Bryce, Charlotte and step-grandson Trevor; her siblings, Paul (Trish), Shaun (Sue), Christopher (Peggy), Tracy (Augie) Aleksy, Regina (Tom) Bober, Molly, Jill (Dan Spitzer), Peggy (Rina), and Siobhan (Attila); her brother-in-law, Peter Thomas; an Abrahamic multitude of 24 nieces and nephews (including Brendan Hunt, who played Coach Beard on “Ted Lasso”) and 20 grandnieces and grandnephews. And she gave Christmas presents each year to all of them.

She was preceded in death by her parents; her brother, Damien; and her sister, Martha.

Visitation will be held at Woodlawn Funeral Home, 7750 W. Cermak Road, Forest Park, on Thursday, Nov. 9 from 4 to 8 p.m. and on Friday, Nov. 10 at Ascension Church, 808 S. East Ave., Oak Park from 9:30 a.m. till 10:30 when a Mass of Christian Burial will be celebrated.

Donations are appreciated to the National Multiple Sclerosis Society ( in her name. 

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