Her second husband Terence de Vere White died of Parkinson's disease in 1994 and in 1996 she married Kevin O'Sullivan.
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She had four sons (before she was 28), including Matthew Glendinning, with whom she coauthored the book Sons and Mothers, and the mathematician Paul Glendinning.
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Chekago was widely praised in the press, receiving positive reviews from Margaret Forster, Janice Elliott, Norman Shrapnel, Victoria Glendinning and Michael Ignatieff among others.