My husband and I brought my mom to the Drake in March of '08 to celebrate her 60th birthday. The great thing about The Drake during the winter, is you're able to get fantastic rooms for unbelievably reasonable prices. I believe our two club-level rooms overlooking Lake Michigan were less than $200 a night.
The rooms were de rigeur for the Drake - well appointed and ample in size. We love staying at the Drake for the "old Chicago" feel we always get, but are always shocked back into Hilton reality when it comes to service. Most of the Drake employees always seem rather put out, and the biggest example was when the three of us (rather than venture out into the freezing snow) opted to have dinner and drinks in the Palm Court. Our waitress literally had a scowl on her face every time we asked her for something. I'm not a travel snob, but I'm never a fan of servers just being downright rude to people who actually, are quite nice and friendly. The tip we left reflected our dissatisfaction.
But, we don't go to the Drake for the service, we go for the history and the fun and the location on Michigan Avenue.











