In Chicago, “The Big Snow” was in 67. Yeah, I was a kid then. But that was the only real mention of snow I can recall through high school. Then 78-79 were a couple of hugely snowy winters. They remain the 2 snowiest winters since 1884. Those made news - in part - because the city did a poor job of handling it, and Jane Byrne used that to help propel herself into the mayor’s office. I was starting college back then in central IL, so I don’t have specific recollections as to how bad those years were in Chicago. In central Illinois it was cold and snowy, but as a student I was walking everywhere so you just did it. When I came home for Christmas, I just recall it being the standard deal, where you would have to push cars out of the snow near the curb into the ruts down the street. My wife recalls getting her car stuck in the snow the first time she came to my parents’ house - which would have been 84-85 winter break.
Chicago’s heaviest year - 89”, is a full 20” heavier than the 5th heaviest. Only 8 years out of 140 exceeded 60”. In 1979, the heaviest single snowfall was 16.5”. That’s a lot of snow. But it was 20 years after that before we got our next 10” snowfall.
On average - and especially lately, winters seem much milder than previously, with much less snow. (He says looking out at a snowy lawn on this umpteenth day of temps in the teens or lower.) 
Not entirely clear to me how different Chicago and Boston’s snowfalls are. Looks like Boston averages in the high 40s - around 48”, with Chicago about 10” less. But other sites make them look more comparable.
