I stayed for 5 days at the Downtown "W" hotel (on Adams St.) on my first trip to Chicago. I had very high expectations. Almost everything went wrong, from a tiny room (probably about the smallest i've ever been in), to a malfunctioning entertainment system, and more. While I know sometimes these things happen, what was most disheartening is the complete lack of care by management and hotel staff to my complaints. Let's just say that this was such a bad experience for me, that as a result I left the Starwood chain (Sheraton, W, etc.) and moved to the Marriott.
Pros: Great gym, great looking lobby
Cons: Small rooms, uncaring staff and management