Huh, I lived in both as well (in the city itself, not the burbs, in both cases), and had a very different reaction. I haven't felt "unsafe" in either city, but

Huh, I lived in both as well (in the city itself, not the burbs, in both cases), and had a very different reaction. I haven't felt "unsafe" in either city, but Chicago feels so much nicer and cleaner in comparison. In SF, however, the trashiness you mention is very much right there, front and center. And I haven't seen people be harassed in CHI like I've seen in SF - there's no equivalent of mid-market, with its luxury condos getting built right next to the TL.