I had the rare occasion to stay in a hotel overnight for a conference, despite living in the suburbs of Chicago. The event was held as the Drake. The lobby, of course, has the big WOW factor if you are looking for a glamorous old beauty of a hotel with that throwback look to yesteryear. Unfortunately, once you get past the lobby the rest of the experience does not impress nearly as much - and at $350 per night - you will get much better value elsewhere. In fact, as a Hilton Honors Diamond member (the Drake is a member of the Hilton family for you frequent travelers), I'd say I get better value at the Hampton Inn. The meeting space in one of their function rooms was poorly lit and dated. The room configuration was also not right for the event. A long narrow room with a U shaped table left it hard to navigate. The distance from the tables to the wall made visibility an issue as well. The foodservice (we had both lunch and dinner in-house) in the conference area was pretty mediocre. In the evening, despite being on the 10th floor (executive level) I could not keep connected to the in-room WiFi. The hotel could do nothing other than patch me to a remote service center twice - yet never was my service restored. WiFi in the conference space worked just fine. Needless to say, zero productivity that evening. In the morning, after a beautiful morning run along the lake front (the hotel location is incredible!), I returned to hit the showers. Right on cue with a full head of shampoo, I am startled by loud banging and a loud voice shouting "Security!" at my front door. Thinking that the hotel might be on fire, I quickly wrapped my soapy, dripping body in a towel and ran to the door to determine what all the commotion was about. Turns out water from somewhere was leaking one floor below. The Drake is an old hotel and while it looks good on the outside, apparently the picture isn't so pretty on the insides of the walls. In summary, beautiful public spaces, superb Michigan Ave/Lake Shore location, staff were pleasant (except for Security) but didn't witness a high level commitment to service, functional space and foodservice found to be subpar, and the customary amenities in the rooms need help. With all the options in Chicago, I'd look elsewhere unless you are really into the look of The Drake.
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