Well before haute takes on Italian food became the “in” cuisine in Chicago, this colossus of a downtown restaurant was simmering red sauce, rolling meatballs, and pouring glasses of Chianti to the brim. The oldest Italian restaurant in the city, which has since expanded and ballooned to become a veritable Disney World of pasta and meat sauce, Italian Village first started out as simply The Village in the heart of the Loop in 1927. Florence-born Alfredo Capitanini opened the restaurant as a culinary ode to various regions in Italy, spotlighting essential eats like chicken Vesuvio, eggplant Parmigiana, and veal saltimbocca. What really left an impression, though, was the immersive and magical decor, including fixtures reminiscent of a countryside villa and a ceiling mural designed to replicate a starlit Tuscan sky. It was apparently so charming that Al Capone was said to be a fan. Then, as Capitaninis kids joined the business in 1955, the family expanded into the basement with another Italian concept, La Cantina, where steaks and chops are the bill of fare in an intimate space designed like a private wine cellar. The Village expanded yet again with The Florentine Room (now called Vivere) on the ground floor in 1961, with an emphasis on more contemporary cookery in a vast and luminous space that looks like a palace out of Aladdin. No matter which enchanting room you visit, Italian Village is the kind of timeless treasure that reminds you of the everlasting comfort of soulful Italian food.
How to book: Reserve via Resy. Carryout is available via Toast and DoorDash.