Historic Hotels in Chicago

1301 North State Pkwy, Chicago, IL 60610 (map)

When it opened in 1926, the Ambassador East was the cat's meow. Originally a residential hotel, the Ambassador was so spectacular that some apartments took up entire floors, and people paid to put their servants up. When Prohibition ended, it jumped on a liquor license, and the simple hotel bar began its evolution into the now-legendary Pump Room, where "Booth One" was reserved for A-list regulars like Frank Sinatra, Judy Garland, Bette Davis, Natalie Wood and John Barrymore. More Hollywood cred: Alfred Hitchcock's 1959 mistaken-identity thriller "North by Northwest" was filmed at the hotel.

636 S Michigan Ave, Chicago, IL 60605 (map)

The Blackstone has earned its nickname, "Hotel of the Presidents," with no shortage of political lore. It's commonly believed that the phrase "smoke-filled rooms" originated here in 1920, when Warren G. Harding was chosen as the Republican presidential nominee behind closed doors. FDR decided on a third term here, and Kennedy's bowl of clam chowder was interrupted by the Cuban Missile Crisis. The presidential suite on the 10th floor even boasts hollowed-out walls for secret service operations and once had a secret door behind the fireplace for quick exits. After a $128 million restoration, the Blackstone is ready to make its name known again, with bigger rooms, colorful design and the swanky tapas restaurant Mercat a la Plaxa drawing crowds.

140 E Walton Pl, Chicago, IL 60611 (map)

With a personality all its own, the Drake is the real McCoy. It was the first hotel in Chicago to air condition all of its rooms and install color televisions, and the last to give up elevator operators and handmade ice cubes. Visits from modern-day dignitaries like Pope John Paul II, Prince Charles and Princess Diana and the Emperor of Japan further the hotel's reputation as a keen stop-off for bigwigs; since opening its doors in 1920, it has hosted Winston Churchill, Elizabeth Taylor, Judy Garland, Hugh Hefner and Frank Sinatra. You can still see where Joe DiMaggio and Marilyn Monroe carved their initials into the wooden bar in the hotel's famous seafood restaurant, the Cape Cod Room.