Have stayed in almost all of the major properties in Chicago over the last 5 years. Don't particularly like the Drake. It's rooms are older, bathrooms are small, and the restaurants are not up to snuff. My favorites are the Intercontinental on Michigan Ave.--if you are in Six continents Club and get an upgraded room (some of the regular rooms are really small and stuffy), or the Fairmont a couple blocks off Michigan near the Lake. It's a terrific new hotel, everything's first class. Hyatt on the other side of the river is just so-so. While I like to double dip, I like the IC and Fairmont so much that I'd rather stay there.