Oh no I didn't mean to imply that in a negative way at all. Its like NY, but way cheaper. My friend bought a nice 2BR condo in a building with a doorman and a pool and balcony on the 30th something floor for 300k. A different friend of mine is spending every other week there for work (we both moved to the same company HQ'ed there), considered buying a crashpad 800 sqft 1BR in "the loop" aka right downtown for a bit over 200k. These are prime locations where you can walk or bike to work. A few stops out on the red line to the north and you can get a lakefront (with a view) 1000sq ft 1BR for <200k as per my trulia search a moment ago.

Salaries are lower than NYC, but not that much. A dev on hacker news should be able to comfortably afford not only to live on his own but to own a place on a single income.

It still has good parks, museums and restaurants, but they are in my experience far less pretentious, and with a few exceptions (ahem Alinea), much easier to get into. There are clubs, there is art, but its all just a bit more muted.

A lot of people love NY for the extremes and the "OMG only in NYC" stuff but I find Chicago to be a cleaner toned down version that doesn't take itself too seriously like NYC often does.