The painting depicts Oona as wife and mother with Chaplin as the The Little Tramp framed in the background. The children are Geraldine and Michael.
The first, second, and fifth photos are from Cinemonde magazine (Nov. 11, 1947) and courtesy of Dominique Dugros (thanks for your help!) All other photos are from Charlie Chaplin by Maurice Bessy (3rd & 4th) & Remembering Charlie by Jerry Epstein (last).
Here the painting can be seen hanging in Chaplin’s foyer at his Hollywood home, at left above the organ. (Chaplin, at far right with Oona, was hosting a party for the Circle Theater players, c. Oct. 1947)