On 27 July 1863 John Ryan married Scottish-Canadian Margaret Isabella McSween, fourth daughter of Roderick McSween, in a widely attended ceremony in Brockville, Ontario. The couple lived in Brockville following their marriage for three decades until 1894 when they moved, along with their four live-in house staff, into a red-brick mansion on the storied
Jarvis Street in Toronto, Ontario. They had seven children: Helen Margaret "Nellie" Ryan, Isabelle Teresa "Rita" Ryan, Maj. John Raymond Ryan, Patrick Hugh Ryan, Roderick McSween Ryan, Charles Alexander Ryan, and Hugh Alexander Ryan Their daughter Isabelle Teresa Pettit (née Ryan) was still receiving payments from this Trust Fund in 1929. On 14 June 1892, Ryan's eldest daughter Helen Margaret "Nellie" Ryan married prominent Montreal-based railway developer Allan Ronald "A.R." Macdonell in Brockville, Ontario. Their daughter Elinor Claire Macdonell married British painter
Raoul Millais, grandson of Pre-Raphaelite painter Sir
John Everett Millais and the son of naturalist
John Guille Millais. A portrait of Elinor by Raoul is housed in the
National Portrait Gallery, London. On 3 April 1908, Ryan's younger daughter Isabelle Teresa "Rita" Ryan married Colonel Hubert Ronal Pettit —appointed
Deputy Lord Lieutenant of Herefordshire by
King George V— in a ceremony in Prescott, Ontario, followed by a reception on the Ryan family's private train which took the wedding attendees to Montreal, Quebec. Both of Ryan's daughters, Helen and Isabelle, were the goddaughters of his eldest brother and business partner Hugh Ryan; and were subsequently beneficiaries of Hugh Ryan's sizeable estate. Ryan's elder sister was heiress
Alice Ryan, known for her work in the Canadian suffragette movement and lavish lifestyle. Through his sister, Ryan was the uncle of
Margaret Isabelle McHenry (née Doheny)
, the president of the
Catholic Women's League of Canada. His eldest daughter, Helen Margaret "Nellie" Ryan, was the maid of honour at Margaret Isabelle's wedding to whiskey magnate William John "W.J." McHenry on 28 October 1885. == Death, estate and funeral ==