Deep winter in Chicago is pretty miserable. I grew up with it and value the changing of the seasons (California has only two seasons: yellow season and wet grey season), but not wanting to gut out February here is a perfectly cromulent reason to avoid the place. If you don't have a pretty healthy social system with indoor stuff to do during the weekend, it can feel a little like living through 2020 did, but for a couple months every year. I'm happy to hang out with the whiskey list at Delilahs, seeing a concert or two, and snagging tables at Publican, Juno, and Duck Inn during those months, but if that's not your thing, I can see how this place would get bleak.