I'm thinking about visiting Chicago next February. I hear it's not the best time of the year to go there, but it's the only time I can, seeing as I have a Delta Airlines voucher for 300$ and apperently that can fly from Boston to Chicago and then from Chicago to NYC.
I feel like I haven't seen you around here in a while!
Anyway, yeah, Chicago in the winter is ... interesting, to say the least But it's also a city where most times, the city is so used to snow and cold that it never like, shuts down or anything when it gets really bad. Waiting for buses and trains in the wind/cold and snow isn't the most fun pastime, but the systems do still run in shit weather so again, it's not like you are necessarily completely limited in your activities if bad weather hits. And it doesn't always! I've been to Chicago in the winter a lot and for as many times we've had to deal with snowstorms and -20 degree temperatures, we've had warmer days (still requiring coats and such, but very bearable) and sunny/partly cloudy days. Of course, I'm saying this as someone who does live in a place where we have winters, so my idea of bearable and your idea of bearable may be very different