Chicago's pavement will always be in difficult shape due to the climate and, more importantly, the incredible amounts of road salt used to keep the roads ice-free.

I am seeing more and more e-bikes though, which, since you can keep up with traffic relatively well, allow you ride in the car lane under most circumstances. That's what I do, and if some dickhead really feels the need to pass me when I'm going >25mph, I'll give them a wave at the next light. And probably be shot in the chest one of these days.