With today being exactly 2 months until Halloween, and coming off of the snow on Halloween 2019, I looked up some October snow stats for Chicago. There have never been back to back Octobers, let alone Halloweens, with measurable snowfall in Chicago.
The probability of measurable snow in a given October is relatively low, but you would think the back to back thing would have happened at some point. There have been a couple instances of measurable October snow 2 years apart.