“The Loop’s oldest Italian restaurant has opened an espresso bar to court morning commuters, Downtown residents and workers.

“Café Pisolino is open on the ground floor of the sprawling Italian Village Restaurant at 71 W. Monroe St. The espresso bar, inspired by the Italian tradition of a pisolino — a short nap or moment of pause — invites customers to slow down and enjoy the everyday rituals of Italian life at the center of the bustling neighborhood.

“‘Café Pisolino is our way of reimagining how Italian Village can serve the city throughout the day,’ Jonathan Capitanini, president of Italian Village Restaurants, said. ‘As the Loop continues to evolve, we saw an opportunity to create something that feels both timeless and new, a place where people can step away, even briefly, and reconnect. It’s about honoring our family’s legacy while contributing to the vibrancy and everyday life of downtown Chicago.’

“Café Pisolino is the newest addition to the Italian Village enterprise, which has been in business since 1927. Italian Village is now run by fourth-generation siblings Jonathan and Giovanni Capitanini, who added the restaurant Sotto and cocktail lounge Bar Sotto to the building’s lower level in 2024 after an extensive renovation.” (Mercado, Block Club Chicago, 6/9/26)

The story behind that nearly century-long run is one of Chicago’s great immigrant success stories:

“An immigrant from a small town nestled in the picturesque, rolling hills of Tuscany, Alfredo Capitanini came to Chicago in 1924 with little money, but big dreams. He knew nothing about restaurants but was eager to work, so he took a job as a dishwasher and began to build his ‘Sogno Americano.’ Just a few years later, The Village was born.

“Alfredo began his new American life as a dishwasher and ended up building a monumental restaurant paying homage to his Northern Italian roots with dishes inspired and adapted from his hometown of Lucca in the foothills of Tuscany. He found immediate success — opening his doors on September 20th, 1927 to a full house. Over the years, The Village constantly evolved, priding itself on always listening to the guests.

“Four generations of la Famiglia Capitanini later, The Village still stands, against all odds, as a bastion of Italian-American tradition, exuberance, and la dolce vita.” (Italian Village, since 1927. A Chicago Legacy Business)

Preservation Chicago celebrates Italian Village Restaurants as a great Chicago Legacy Businesses — and one of the finest examples of what it means for a family enterprise to remain not merely open but thriving and evolving for nearly a century.

The addition of Café Pisolino is the latest proof: a fourth-generation family business that understands its own history well enough to extend it thoughtfully, reading the Loop’s changing rhythms and finding a new way to serve customers without abandoning what made the original use so special.

Italian Village occupies a multi-level building at 71 W. Monroe that is itself a fixture in Chicago’s downtown commercial fabric. The main dining room’s interior — the pressed-tin ceilings, the murals, the warm light that has washed over generations of Chicago diners — is the kind of environment that cannot be replicated and should never be taken for granted. That it remains in the hands of the family that built it, and that those hands are now extending the enterprise from breakfast coffee to late-night cocktails, is a preservation story as much as a restaurant story.

Preservation Chicago encourages all Chicagoans to visit Italian Village, Sotto, Bar Sotto, and the new Café Pisolino at 71 W. Monroe Street.

Read the full story at Block Club Chicago

• Café Pisolino Wants You To Pause For Coffee, Pastries At Its New Home Inside Italian Village, The espresso bar is the latest offering from the family-owned restaurant, which has operated Downtown since 1927, Melody Mercado, Block Club Chicago, 6/9/26
• History of the Italian Village, since 1927. A Chicago Legacy Business
• Italian Village celebrates 98 years with ‘blast from the past’ menu; ABC7 Chicago, 9/23/25
• History of the Italian Village, since 1927. A Chicago Legacy Business
• Italian Village Restaurants
• 71 W. Monroe St., Chicago, IL 60603
  (312) 332-7005