On December 5, 1933, the 21st Amendment was ratified, bringing an end to Prohibition. It couldn’t have come at a better time for Chicago brothers John and Tracy Drake, whose new seafood restaurant, the Cape Cod Room, opened December 6 inside their eponymous hotel at the base of the Magnificent Mile. With its low-lit nooks and New England–inspired nautical theme, the Cape Cod Room soon became a magnet for visiting celebs like Henry Fonda and Mickey Rooney, rivaling the Pump Room as one of the city’s most hallowed haunts. Everyone would pop by The Drake, grab a seat at the wooden bar, where guests like Marilyn Monroe and Joe DiMaggio once carved their initials, and cavort while savoring a cocktail and just-shucked oysters. Eighty years later, the restaurant (now named, simply, Cape Cod) is still an attraction, as one of the grandes dames of the city’s dining scene. Tucked away in the first floor of The Drake hotel, the dining room hasn’t changed much: taxidermic fish and crabs dot the walls, copperware hangs from the ceiling, Cape Cod–engraved pewterware adorns the tables, and veteran servers like Steve Spanos (53 years) and Spyros Theofanis (40 years) still fillet Dover sole tableside while regaling guests with stories of the celebrities who once sat at their table.

“It was absolutely the place to be, as the whole Drake was,” says socialite Hazel Barr, recalling the restaurant’s heyday in the ’50s to ’70s. “You’d say, ‘Meet me at the Cape Cod Room,’ and we’d have a drink there.” Even in the face of 21st-century trendiness, the room’s old-school splendor still charms, thanks to its enduring traditions. Once seated at a table, guests’ water glasses are filled with ice from a stainless-steel bowl, and a server offers warm greetings and recommends one of the restaurant’s classic dishes: iconic Bookbinder soup, a tomato-based broth studded with red snapper; garlicky Shrimp de Jonghe (a Chicago original); steamed Maine lobster that the room captain gladly cracks; the signature Dover sole (“without a doubt” the most popular dish on the menu, according to Executive Chef Baasim Zafar); and sides of decadent Maine lobster mashed potatoes.

For Kirk McKie, Cape Cod is about family. She has a relationship with the restaurant dating back to the 1940s, when her grandmother would spend winters living at The Drake and her father, Lawrence Williams III, then living in Lake Forest, would visit his mother and they’d dine here.

While growing up in Peoria, McKie and her family would travel to Chicago for events or Christmas shopping, stay at The Drake, and dine at the Cape Cod Room—just as her mother did with her parents. Today McKie and her husband, who live in Chicago, have regular dates at Cape Cod for drinks and Bookbinder soup. “As you see Chicago continue to evolve, you see some of these institutions frequented less,” McKie says. “That historical element of the city [is] how we ended up being here today. I still love Cape Cod.”

It’s these personal connections that make Cape Cod a classic. And as the restaurant prepares to celebrate its 80th year, there’s a sense of excitement about bringing this iconic restaurant back into the spotlight. “The anniversary is an opportunity for us to reintroduce the Cape Cod room to Chicagoland,” says general manager Ted Daskalopoulos. “It used to be all locals—politicians, upscale Gold Coast customers, VIP personalities. Over the years that has changed because of the trends. Now we have a lot of out-of-towners—it’s become famous and somewhat of a tourist attraction. People want to be part of the history of this famous place.”

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