I live and have lived in the chicago metro my whole life. There are few places I could imagine moving to if I could go anywhere. Obviously im biased. One thing is I need good public transit. I never thought how good ours may or may not be till I went to a job interview in dc. I swear it was middle of the day and the trains ran like every 20 mins. In chicago they only run that unoften at like 2am. then like getting off and going on a buss you paid basically full fare. got a 25 cent discount or something. here you pay your fair and you can transfer twice outside the system (bus to diff bus or bus to train or train to bus. transfers train to train are always free and don't use a formal transfer). I think maybe only new york might have a system that is adequate enough for me in the us outside of chicago. add to this great bike lane infrastructure and the divy bike program and the extended train network with metra and its central location to amtrack plus two major airports. then like the lakefront, parks, forest preserves often around the rivers. its not bad for nature spaces for such a big city. then like you can find food from anywhere between the city and the suburbs. also four seasons which can be a plus or minus but is a plus for me. when you have nice weather in chicago you effing appreciate the heck out of it.