I was based out of ORD for 4 years and enjoyed the times I ventured into the city. If I thought that I would be based there the rest of my career, I'd have moved my family to one of the less draconian areas surrounding Chicago in a heart beat. Of the 4 big cities in the US, Chicago is my favorite. It is beautiful, full of culture, good food, and a lot of good people. POTUS and his cronies excepted, I don't get the elitist "I hate the US" attitude which is quite prevalent in LA and NY. Rather the average Chicagoan I came in contact with was true to their midwest roots. Damn shame the bad guys have such a choke hold on it.
Good luck and enjoy!