Not worth the expense! Hate being nickel and dimed...
First of all, I was shocked by the high price of our room the 4 nights we were in Chicago, considering that the same room cost several HUNDRED dollars less the weekend before and weekend after... Also, our AAA and government statuses were not honored for a rate reduction, and Sun/Mon rates were as expensive as Fri/Sat rates. Why? I understand supply and demand and that some weekends are busier than others, which explains IN PART the huge price increase, but I've never known a hotel to not honor AAA or government status. 
We had an "executive" room, which had a wonderful view, and the room was quite comfy, but at check-in, no one on staff ever told us anything about the executive privileges, until we called and asked, at which point we were only told about breakfast, not the afternoon cocktail/hors d'oerves (we never knew about this or any other privileges until another guest told us the last day of our stay... terrible service). Moreover, when we tried to use our room key to access the executive suite where breakfast was to be served, we were denied and had to call from the hallway downstairs to reception, at which point the desk clerk connected us to our own room via phone, rather than connecting us to the staff in the executive suite... of course, then we had to call downstairs again. Very annoying.
One of the most frustrating parts of our stay was the lack of complimentary in-room wireless internet. We were paying $400 a night for a room for 4 nights (!), and we're Hilton Honors members, and the Drake couldn't comp our wireless internet??? That is terribly cheap on the hotel's part. I have stayed at far lesser hotels and not been nickel and dimed for wireless internet. The business center downstairs also tried to nickel and dime guests, by charging ridiculously high rates for time on the internet and printing. On top of that, a beer (Amstel Light) from the bar cost $9!! That's insane for a hotel bar, even in Chicago.
On a good note, the hotel was very clean and well-decorated, and the Friday night swing band was a wonderful surprise.
Overall, very poor value for the money. We won't be recommending this hotel to others.