The Drake Hotel was once the grand dame of Chicago luxury, and walking into its elegant, formal lobby is like entering Gatsby’s West Egg. While modern hotels have really shrunken their lobbies, the entry here is multiple levels, and the harp music emanating from the Palm Court tearoom is the perfect soundtrack with which to explore. The comfortable rooms have been updated in a way that’s actually taken away some of the character of years gone by, but considering the price and ideal location, I won’t complain. Rooms facing north offer only-in-Chicago views of Lake Michigan and Lake Shore Drive (those rooms come at a premium). To experience even more grandeur, make a reservation for dinner at the Cape Cod Room and enjoy classics such as clams casino and Lobster Thermidor before having a Manhattan at Coq d’Or, a boozy throwback of a lounge that opened at the end of Prohibition.