Even worse than the cold imo is the 'about to be cold' weather preceeding and following winter. Rain that freezes overnight and encases your car right when you have to run to work. Muck and mud everywhere the minute you step off a path. Everything green turns to brown. Coupled with the limited daylight and it's depressing, frankly.

I grew up there, and really the worst part was that stretch in February where it's overcast every single fucking day.

Then there's the humidity with 100+F days in the summer. And mosquitoes.

The other problem was I grew up in a reasonable, livable suburb, and now, when I go back there, I see that rents and housing are really extremely expensive compared to salaries. Jobs suck (there's no real tech industry anymore). And traffic in the suburbs is constant gridlock wherever you go. It's become a real horror show and I couldn't ever contemplate moving back. Weather/Climate is not even the consideration.

When the polar vortex dipped down in 2014 and 2019, wind chill did get that low in Chicago. I think it actually hit -50 F on the coldest day for one of them.