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
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.

Pump Room

Pump Room was so loved by Sinatra that it got a shout-out in his song “My Kind of Town.” He sat in Booth One, the preferred table of many celebrities. In September, the restaurant launched a nightly Sinatra Toast to celebrate his 100th birthday year, with plans to make it a daily tradition. On Frank’s actual birthday, guests will be able to choose from a menu of the singer’s favorite meals.

Miller's Pub

Think of Miller’s as the Cheers of Golden-Age Chicago. Frank’s framed photo still hangs on the pub’s wall, surrounded by hundreds of other signed pictures from celebrities who’ve frequented the bar throughout its history. Though no longer owned by the Miller family, the bar was always one of Frank’s favorites.

The Green Mill

The movie The Joker is Wild tells the story of singer Joe Lewis, who was attacked by mob men after refusing to perform at the Green Mill. Sinatra played Lewis in the movie and spent plenty of time rehearsing (or maybe just drinking) at the lounge. A Chicago institution since 1907, The Green Mill has a checkered past. Home to jazz greats, it was once partially owned by a member of Al Capone’s outfit. It became a popular speakeasy complete with bootlegger tunnels beneath the building. Yes, the tunnels are still there. No, tours are unfortunately not given.

Mister Kelly's/Gibsons Bar & Steakhouse

Stop by Gibsons for a steak and you’ll likely hear one of Frank’s tunes. One of Chicago’s top steakhouses, Gibsons plays Sinatra’s music frequently to pay homage to the time the crooner spent at the restaurant’s predecessor, nightclub Mister Kelly’s. Sinatra hung out here with a group of fellow jazz greats—many of whom also served on the nightclub’s staff during hard times. Gibsons is now frequented by Chicago’s elite, keeping in line with Mister Kelly’s revered history.

Gene and Georgetti

Sinatra loved the food at Gene and Georgetti, which, like Gibsons, is a long-time celebrity home. The restaurant has served steaks to guests ranging from Sinatra and Lucille Ball to Keanu Reeves and Will Ferrell and still attracts devoted regulars, some of whom have been coming for over 50 years. Owner Tony Durpetti tells Gerzina that Sinatra preferred to dine without the rifraff or the regulars: He always came in after the restaurant was closed and could be found eating dinner there with friends late into the night.

Rosebud

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.