The Drake, A Hilton Hotel

Travelers love the Old World elegance than defines The Drake: think New York's Plaza Hotel done Chicago-style. Once the preferred choice of both Winston Churchill and Princess Diana, this Gold Coast neighborhood outpost knows how to deliver a quality experience. (If you really want to blend in with the posh clientele while you're here, recent guests suggest attending the traditional English tea service in the Palm Court, offered every afternoon.) Unlike its trend-setting neighbors, The Drake boasts a distinctly vintage ambiance with high ceilings, upholstered walls and glittering chandeliers. Though recent guests admitted the hotel could use some remodeling, they also said the property's old-fashioned style is exactly what makes it so charming. And because of its Hilton Hotels ties, guest rooms here include signature Serenity beds and Italian marble bathrooms, as well as modern amenities like flat-screen HD TVs and high-speed internet access (for a fee). Plus, if you're a member of the Hilton Honors program, you can accrue or redeem points here.