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

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 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.

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 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.

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.

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 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.