The long history and stellar location of the Drake make it a fun place to stay. One really feels like he stepped off of Michigan Avenue and into Old Chicago when entering the lobby here. The hotel, though now clearly a fully-fledged Hilton, still retains many of the old characteristics of yesteryear, including elegant furnishings and unique carpeting.
The service is, generally, very good, though the bellman should have offered to carry my luggage up the stairs to the lobby instead of just watching me carry the suitcase. The room was spacious and well appointed, and the executive lounge was one of the best I've visited within the Hilton chain.
Still, there are signs that a renovation should come within the near future. Some walls have been painted over one too many times, and the bathroom plumbing could be a bit finicky at times. That said, despite the aging infrastructure the hotel was kept very clean and orderly. If given the choice between the Drake and other upscale chains (e.g. Marriott, Westin, other Hiltons...), I would choose the Drake again. If for nothing else, the history book about the hotel left of my coffee table was fun to flip through.
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