As long as the rooms are clean, not too small and reasonably attractive, I am not too fussy. The room I had most recently had at the Marriott had a wonderful view of the lake and I loved it.
The only thing that really matters is, how far is it from the Miracle Mile? If I am in a shopping mood I pick the Marriott or Westin or Drake. I am not as fanatic about hotel points as I am about air miles. Maybe I'll catch that compulsion if I hang out here a while longer.
Usually I go to Chicago to speak at a conference and then I stay in the headquarters hotel, whatever it might be. Often the Sheraton on the River, or next month it is the Hyatt Regency. I also really like the Hilton and its proximity to the lake.