That's my mom, Mary Alice Hogan, posing with Old Glory. There's no date on the picture, but I would guess this was the 4th of July and that she was about 16. That would place the picture in 1945 or '46. A further guess: The picture was taken at her O'Malley-Moran grandparents' place at 6524 South Yale Avenue in Chicago's Engelwood district (the family moved there from their Stockyards neighborhood sometime between 1900 and 1910 and stayed through the early 1960s. The house was torn down sometime in the past 15 or 20 years, and there's a vacant lot there now).
Below is my dad. The picture is actually dated September 30, 1928, when he would have been seven years old (and 14 months before Mom was born). I have no idea why he's wearing the funny lady's hat or carrying an American flag or wearing whatever that is around his neck. This would have been about three years after his family moved back to the city from Alvarado, Minnesota, where his dad was a Lutheran pastor for several parishes in town and the surrounding area. They lived on the South Side through 1930, at West 71st and South Ada streets. One other thing I take note of after staring hard at this picture: the suit that my dad's wearing. That is some serious-looking fabric.