Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (2025)

In the 1980s, Ray Capitanini increased the number of wine offerings at the Italian Village, his family’s Loop restaurant, from about two dozen to nearly 4,000 wines.

“He really treated wine like an investment and put us on the map for a different segment of the population who came in from across the country to dine here because of the wine,” his nephew Al Capitanini said.

Mr. Capitanini died April 10 from respiratory issues after heart surgery. He was 89.

Along with his brother, Frank, and sister, Ave, he was part of the second generation of their family to run the restaurant — Chicago’s oldest Italian restaurant — at 71 W. Monroe St. Their Italian immigrant parents, Alfredo and Ada Capitanini, started the business in 1927.

Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (1)

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Mr. Capitanini, the youngest of the three siblings, was the restaurant’s table-hopping maitre d’. He’d mingle with patrons who included many well-known names over the years, among them Barbra Streisand, Frank Sinatra and Luciano Pavarotti.

“He’d sit with them and chat and share stories,” Al Capitanini said, noting that his uncle always started his night at the restaurant with a negroni before moving on to a couple of glasses of wine and finishing the evening with a glass of Hennessy X.O cognac.

Back when Streisand was singing at Chicago nightclubs, “The Italian Village was the first restaurant she ever ate in in Chicago,” according to Pamella Capitanini, Al Capitanini’s wife, who said the singer liked the pasta primavera. “Frank and Ray were so proud.”

Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (2)

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Mr. Capitanini loved being around people, according to his family. He’d be the first on the dance floor at weddings and the last off, occasionally firing off a few sets of pushups in between.

“Ray just would have a very good time,” said his niece Lisa Capitanini, an investigative news producer with NBC5. “He was not inhibited in any way.”

In 1961, Mr. Capitanini oversaw the opening of the upscale Florentine Room inside the trilevel building that houses the Italian Village. The Florentine has since closed, but the Italian Village remains and also includes two other restaurants and an event space in the same Loop building that are run by fourth-generation members of the family.

Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (3)

Sun-Times

In 1992, Chicago Sun-Times restaurant critic Pat Bruno wrote of Vivere, the restaurant that replaced the Florentine Room: “I would be remiss not to mention the outstanding selection and collection of Italian wines that has put Italian Village on the wine map. Its collection of vintage Barolo and Barbaresco and Brunello wines alone is enough to make the fussiest of wine snobs sniffle with pleasure.”

Mr. Capitanini lived in Lincoln Park with his wife, Nada, who died in 2008. His garden was a perennial highlight of the Sheffield Garden Walk.

Mr. Capitanini loved art and music and was a supporter of the Lyric Opera of Chicago, the Chicago Symphony Orchestra and the Goodman Theatre.

A diehard Cubs fan, he cherished attending World Series games in 2016 with his brother, Frank Capitanini, who died in 2018.

Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (4)

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“Every person I called on his contact list started crying when I told them he died,” Al Capitanini said. “He helped a lot of people who were down and out over the years.”

Born July 28, 1935, Mr. Capitanini grew up in River Forest, attended Fenwick High School and graduated from the University of Notre Dame.

He owned a car but rarely drove, favoring public transportation.

“He really was someone you could have a conversation with and really talk about everything,” said his nephew, adding that Mr. Capitanini spoke fluent Italian. “Ray was sort of that guy that everybody wanted to be.”

Services have been held.

Ray Capitanini, wine maestro of Italian Village in the Loop, has died at 89 (2025)
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