We stayed for a weekend and had a wonderful time. The Hotel lobby was beautifully decorated with fresh flowers. We used the hotel concierge several times and unfortunately we felt misled. We asked for a reasonably priced steakhouse and they sent us to Rosebud's. It was a very expensive meal and the aged meat tasted rotten. We also asked for a great hot dog and they sent us to Portillo's. The hot dog was cold and the Big Beef Sub had no flavor. It was a Cute fast food restaurant but I am sure not the best hot dog in Chicago. The hotel staff were friendly and the room was quite nice and clean but the bed actually sloped down on each side due to years of use. The sheets and pillows were very soft. The workout room was excellent. Lot's of different modern exercise machinery, lot's of fresh towels and was much like a private spa. The Hotel had several restaurants and some were surprisingly reasonably priced.
One lesson from the trip was to use TripAdvisor for the restaurants as later I read the reviews on the restaurants and they were very accurate and better than using a concierge. I would definitely stay at the Drake again.