The Luxurious Chicago Restaurant Where You Can Dine In Frank Sinatra's Booth

Frank Sinatra wasn't just a legendary crooner; he was an actor and a record label founder, but he was also very much a man about town. He liked to see and be seen, evidenced by the various public places he frequented during his lifetime. Sinatra made Patsy's Italian Restaurant a New York staple, and he frequently dined at Las Vegas' Golden Steer Steakhouse — specifically table 22. And when he was in Chicago, Ol' Blue Eyes could be found at The Pump Room at the Hotel Ambassador, where he sat in the storied Booth One.

In fact, Sinatra was so smitten with the historical restaurant that he paid homage to it in his 1964 song, "My Kind of Town" in which he mentioned "the jumpin' Pump Room." The Pump Room first opened in 1938 and was designed to be glamorous, with crystal chandeliers and leather banquet booths. It quickly drew the attention of high society who all wanted to be seated in Booth One, which offered the best view of the restaurant. Sinatra was just one of many notable names to be seated at this desirable table; others included famous actors of Hollywood's Golden Age, politicians, artists, and royalty. Alfred Hitchcock even filmed scenes for his hit 1959 movie "North by Northwest."

After several ownership changes and remodels over the past century, the hotel and restaurant — which is now named Ambassador Room — still stand, and the historical booths remain open for seating, including Booth One. But where you once needed to be quite famous to sit there, selectivity isn't nearly as cutthroat anymore.

During the mid-20th century, when the Pump Room was in its heyday, the scene inside included lots of flashbulbs, celebrities on the telephone (Booth One had its own private landline), and white-jacketed waiters serving shish kabobs en flambé on real swords to hungry guests. Diners had to adhere to a strict dress code or be shown the door (This actually happened to singer Phil Collins who arrived sans jacket). Today, things are much more relaxed at The Ambassador Room; so much so, that Frank Sinatra and friends might not recognize their old stomping grounds.

The menu is definitely varied, but reads a little like TGI Friday's; appetizers include fried mac and cheese bites, pepperoni pizza, wings, and mozzarella sticks. The food doesn't necessarily fit a cohesive culinary theme. On one hand, you can order a quinoa bowl with roasted vegetables, or a Peruvian beef dish called lomo saltado; and on the other, you'll find burgers, wraps, bowls of chili, and pastas. It certainly doesn't give any indication that turban-toting servers used to theatrically serve coffee drinks to people dressed to the nines. But even so, if you want to enjoy Bavarian pretzels, tabletop s'mores, and maybe a cocktail ordered exactly how Sinatra liked his martinis — in the same place he drank them — all you have to do is grab Booth One at The Ambassador Room.