Frank Sinatra may have been a blue-eyed boy from Hoboken, but he had a real thing for Chicago. Sinatra claimed that he performed in Chicago more than any other city—even Vegas. It was where he made a name for himself as a performer, first working the room as an opening act at the Sherman House Hotel and then finding fame when he took up with the Tommy Dorsey Orchestra at the Palmer House.
During the singer’s heyday, he had the run of the streets with his Rat Pack pals and celebrities including Marilyn Monroe and Ella Fitzgerald. Between performances, he spent hours tucked into local clubs. Even his love affairs reflected his love of the city: When Sinatra married Barbara Blakeley, he made sure to have his wedding reception at the Italian Village.
But the crooner of songs like “Chicago” and “My Kind of Town” was also part of the city’s dark side. In 1960, he allegedly helped Chicago mobsters buy votes for the John F. Kennedy campaign. When the mafia came under investigation during JFK’s term, Sinatra paid the price—by playing eight consecutive days of forced performances with the Rat Pack at mob boss Sam Giancana’s night club in the Chicago suburbs.
You can still tour or see a show at many of the performance venues where Sinatra took the stage, but why not toast the singer's 100th birthday on December 12 from one of his favorite watering holes? Each of these bars and restaurants was frequented by Sinatra and his cronies, and together they make up a delicious tour of Frank’s Chicago. If you’re going to raise a toast to Ol' Blue Eyes, consider doing it with a Jack on the rocks. Frank would prefer it that way.
Rosebud is a chain, but the original location on Taylor Street was one of Sinatra’s favorite restaurants. Be sure to check the wall for Frank’s picture and relics highlighting his many visits, and ask the staff to point out Frank’s favorite table. The Italian eatery is still beloved for one of Sinatra’s favorite meals: homemade square noodles, perfect for slurping.