Eat (and Drink) Your Way Through Sinatra’s Chicago

See why the Windy City was without a doubt his kind of town

The Green Mill Cocktail Lounge, once partially owned by a member of the Chicago mafia syndicate. (Photo by BriYYZ on Flickr)

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 cityeven 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.

Twin Anchors

Sinatra’s agent first brought him to Twin Anchors to try the ribs—and Sinatra stayed. The singer became a regular, stopping in frequently as he played his way through Chicago. Mary Kay Tuzi, who co-owns the restaurant, tells Chicago Eater’s Daniel Gerzina that when Sinatra came in, the restaurant would shut down to new diners while he had dinner and drinks with his buddies. He was  known to post a bodyguard at the payphone so no diners could alert the masses to his presence. At the end of the meal, he’d tip everyone $100.


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