Chicago Hotel (downtown)
Personally I stay regularly at the Crowne Plaza Metro - 10 mins walk from downtown, close to all the Greek restaurants. The Hotel was recently refurbished - it's great (in my opinion). Staff are relazed and friendly...I ended up joining the doorman and his mates at a Blues place.
I get a corporate rate of $129/night and am close to where I need to work when I'm in town.
I mut admit that I haven't stayed at any other Hotel in Chicago so cannot compare.