i'm not sure how this became the unofficial denver v. chicago thread
...but i've lived in both cities, twice!
there is simply no comparison between the two...it would be a bloody, bloody battle for denver. keep in mind that chicago is essentially one half of nyc - half the people and half the skyscraper count. it's a totally different league than denver. there are some fiscal issues for the city / state....but it's being fixed by a new governor (R) and Rahm is doing a pretty darn good job (D). It's certainly not as dire as DenverPoke seems to think
the cost thing boils down to drinks / food I think....much pricier here. otherwise, it's about the same on cost - and you barely need a car (i drive about 2x / month...) so you could save $500 / month easy by not having a car. the walkable areas of the city are vast.
weather? it's the one area that denver crushes chicago...but this is what business trips and holidays are for during that bad 5 months.