The Drake, a Hilton Hotel

Courtesy of the Drake / Expedia
If you’re looking for a stay in a 1920s Italian Renaissance building, complete with ornate staircases, chandeliers and a ballroom, the Drake is the place for you. It sits on Chicago’s Magnificent Mile and its north-facing rooms boast sparkling views of Lake Michigan and Oak Street Beach. Enjoy eggs benedict in the hotel’s Café on Oak, where Marilyn Monroe and Joe DiMaggio’s initials are carved onto the counter, or afternoon tea in the Palm Court lounge, once visited by Her Majesty Queen Elizabeth II.