Winter in a place that actually has a winter is terrible. You're stuck inside all the time, have to wear 15 different things so you don't freeze when you do go outside, the sun just decides not to exist for months, roads get icy, you have to humidify the air so your lungs don't shrivel up. Meanwhile, winter is great in a place where it's just a different flavor of summer. The coffee shop has new drinks! All the mosquitoes are dead! Charlie Brown Christmas! Wearing scarves because they look nice, not because you're worried about your jugular turning into an icicle! Flip side is that summer in a place like Florida is hell, and summer in a place like Chicago is incredible.