Magnificent Hotel on the Magnificent Mile
The Drake has fantastic old world charm but manages to still feel hip and relevant.
As soon as you enter the lobby you know that you are in a true classic. The decor is beautiful and the staff very gracious and friendly. The rooms may not have all the electronic amenities of a super modern hotel, but the classic charm and feel more than make up for it.
The location at the top of The Magnificent Mile is absolutely perfect - you can walk to everything but it is just slightly removed from all the hubbub. 
Also, the service is outstanding. My sink was slightly clogged - I called guest services and when I returned about an hour later not only was it fixed but they left a little note telling me so. Nice touch! 
Breakfast at The Drake Brothers was good; I would suggest ordering off the menu as opposed to the buffet. 
Also - Hilton Honors members get fantastic upgrades here - or at least I did. The Executive Suite with a lake view is amazing!!!