Earlier quoted context omitted.
I've lived there for a while and there were a lot of deal breakers for me: * security: you feel unsafe in most of the city, past a certain hour and you can't walk nor take the public transit (actually even during the day, the public transit is filled with crazy people). I could never take walks around my place when I was living there. A lot of poverty. * no real life: there is the loop, but it's mostly offices and it…
It's a big city. There is big city crime. Your nightlife thing is pretty weird. The Loop is Chicago's business district. It is dead after business hours. Don't be there. Wicker Park and Logan Square are neighborhoods, not single streets. There's also Lakeview, Avondale, Pilsen, Andersonville, and a bunch of others I'm forgetting. Maybe the argument is that together these neighborhoods constitute a pretty decent night…
Compare that to London or Beijing where you feel safe at all time. Being a big city is not an excuse for feeling unsafe.
> Wicker Park and Logan Square are neighborhoods, not single streets
After one or two streets there is not much to see. Again I'm comparing this to european cities/asian cities where you can walk for hours in lively old centers/districts.