As the preferred stop for visiting heads of state, the Drake is the grande dame of Chicago hotels, with a prime location, storied history, white-glove service, and of course a distinguished guest list. The experience begins in the palatial lobby, where the ornate crystal chandeliers, soaring wood-paneled ceiling, and red upholstered walls conspire to make guests feel like royalty, especially when enjoying high tea in the gilded confines of the Palm Court. The 535 guest rooms and suites, traditionally outfitted with Regency-style furnishings, combine a scattering of antiques with crisp white bed linens. Those who are lucky enough to score rooms facing north and east have unobstructed views of the lake and Lake Michigan’s Oak Street Beach.
Tip: Have a drink in the Cape Cod Room restaurant, where you can still see where Joe DiMaggio and Marilyn Monroe carved their initials in the wooden bar.
Room to Book: No. 550, the luxurious six-room Presidential Suite, where Princess Diana stayed during her 1996 visit to the city.