Chicago
Pros: Lakefront path,the el, affordable living
fun things to do for free if you know where to look-there's good events at millennium park, museums, story telling events, and other random stuff. The other week I went to a free rowing clinic put on by a boating club that also offered free stand up paddleboarding classes for the day.
good running culture- it's not weird for people to run. Most people will ask if you are training for the marathon. There's plenty of sub-elite runners to hook up with for training runs.
Cons:
Although there are some trails nearby, there are no large state parks, camping, or backpacking within a two hour drive (I've lived in three different states in which I've been within a 10 minute drive to the Appalachian trail). Unions are corrupt, police are corrupt, city officials are corrupt, state officials are corrupt. In line with that, all the gov't budgets are bankrupt and crime is significant. Topography is boring.