I found these photos last night while doing some research. Chicagoan or not, I think you'll get a kick out of them.
My neighborhood, circa 1955. Notice the horrid 1000 Lake Shore building in the distance. (Palmolive to the right)
Old Chicago wouldn't be complete without the old Palmer mansion.
These pictures were taken in the 1940's.
Ugly, yes, but still a shame it was torn down in 1951.
Cyrus McCormick's mansion in McCormickville, (West of Michigan Ave.) torn down as well.
City skylines, circa 1950's.
Keep in mind that at this time Prudential was the tallest building in Chicago..