I actually find this freeze thaw cycle in Chicago to be thoroughly depressing...no snow, cold rain, cold wind...Chicago winters are dismal.
Not to mention Chicago gets the least snow of any place on the great lakes, rarely gets big winter storms, and generally is accompanied by 700mph winds wailing off the flat, treeless plain that surrounds the city.
Having lots of snow is depressing, give me -10 and wind for the whole winter and no snow and we're fine.
I understand the sentiment but I don't believe you would really prefer -10 and wind and no snow for months. It would probably result in much of WI's forests permanently dying as the ground freezes too deeply and thoroughly to keep the tree roots protected. Your house pipes would constantly freeze. And you'd be very depressed.
The same goes for deep, constant snow for months.
The winter of 2013/2014 was the worst in nearly 80 years in MN. We had weeks of below zero, heavy snow, etc. Pipes froze, roads got ravaged, and immense numbers of trees died. There were blaze orange evergreens all over. It saps the life out of you.