Jonathan Capitanini remembers when, as children, he and his sister, Giovanna, would tear through Italian Village, their family’s collection of restaurants under one roof in the Loop. “We grew up there, running around all the different kitchens, the tables, the line.” Now part of the fourth generation to operate Italian Village, the siblings are putting their own stamp on the place by modernizing the business. They recently opened two concepts in the basement: Sotto and Bar Sotto.

Italian Village has never been static. In 1927, their great-grandfather, who’d arrived from Italy three years earlier, opened what is now the Village, the upstairs restaurant in this building at 71 West Monroe Street. In the 1950s, the family bought the basement space and opened La Cantina Enoteca, a dark piano bar with a seafood menu. “This was the place you could have your drink, probably bring your mistress, do business,” says Capitanini.

During the ’60s, the family acquired the first floor and opened the Florentine Room, one of the first Italian fine-dining spots in the U.S. The tuxedoed waiters and tableside service attracted crowds, including notable celebrities of the day. In the late ’80s, the next generation renovated the first floor into Vivere, which now operates as a private dining space.

Now it’s the younger Capitaninis’ turn. When Jonathan, who was working in consulting, made his way back home during COVID, he started updating things. Much of the building’s infrastructure hadn’t changed in 50 years. “We had 87 separate light switches to turn everything on and off in the Village,” he says with a laugh. “We were still doing paper reservations!”

Sotto and Bar Sotto — both of which you can book on Resy — bring Italian Village into a new era. Sotto, which maintains the cozy feel of the previous iteration, serves what Capitanini calls “new Italian American” cuisine. While some dishes are recognizably from the old country, others are inspired by immigrants from other countries who passed through Italian Village’s kitchens over the years or by chef Steven Mendez’s travels.

“We are trying to write our part of the story, not being born in Italy,” Capitanini says. “I don’t speak Italian. So how do we be authentic to ourselves?” The answer: through clever dishes like giardiniera-braised short ribs or black garlic pappardelle with truffle and shoyu, which tap into Italian influences but are hardly the red-sauce food of yore. Bar Sotto, a neon-lit spot off to the side, takes a similar approach. Here, Jared Gelband has created cocktails that sound weird on paper — you’ll find Parmesan-infused vodka espresso martinis and Calabrian-chile-spiked margaritas — but somehow work and draw Loop workers.

The Capitaninis aren’t done yet. Some possibilities: an update to Vivere and the addition of a deli and grocery store. Italian Village may look a little different than it did when they were kids, but the Capitaninis plan to be running around the building for years to come.