15 real spots, ranked by the Chicago Specials Score β plus the real Taylor Street history behind two restaurants still run by the families that founded them.
Chicago Specials β Chicago's Best β Italian
Taylor Street is the oldest continuously Italian neighborhood in Chicago. Two of the restaurants on this exact list are run by the same families that opened them, generations ago.
15 contenders, ranked by the Chicago Specials Score
Chicago's Little Italy formed in the late 1800s around Halsted and Taylor Streets, next door to Jane Addams's Hull House — mostly Sicilian and Southern Italian immigrants, in numbers large enough that Hull House's very first invitation to neighborhood residents, in 1890, was written in Italian. Our Lady of Pompeii, founded in 1892, is still the oldest Italian-American church in continuous use in the city, and it's still standing on Taylor Street today.
The University of Illinois at Chicago's construction in the 1960s cut deep into the neighborhood's footprint — the same decade, and the same Eisenhower Expressway-era construction wave, that pushed Greektown a few blocks north around the same time. Two immigrant neighborhoods, reshaped by the same piece of infrastructure, a few years apart.
What survived, in places, is still run by the families that started it. Joseph DiBuono and his wife Theresa Tufano DiBuono — she cooked from her own kitchen next door and passed the plates through a connecting window — opened Tufano's Vernon Park Tap in 1930 or 1931 (sources differ by a year); their grandson Joe DiBuono has run it since 1980, it's cash-only, Nelson Algren used to stop in before White Sox games, and the James Beard Foundation named it an America's Classic in 2008.
A few miles east, in what's now River North but was then a stretch called Smoky Hollow, Gus and Ida Lazzerini took over Club Lago in 1952 and started feeding Tuscan food to printers and paper salesmen. Their son-in-law Francesco Nardini left a career as an accountant to take it over in 1980, and in 2000 he passed it to his own two sons, Guido and GianCarlo — three real generations, the restaurant's 1950s interior apparently unchanged enough that it got cast as itself in the 1991 Robert De Niro film Mad Dog and Glory.
The list above runs from those old-school institutions through destination restaurants (Monteverde, Gibsons Italia) to delis and bakeries that never needed a dining room to matter (Nottoli & Son, Paola's Delights). Italian food in Chicago didn't stay on one street any more than Greek or Korean or Filipino food did — it just had a 130-year head start. That's the real city behind the four letters every time we write I ❤ Chi.
200+ spots, 15 categories β jump straight to another ranking.
Sources: Wikipedia, the Taylor Street Archives, Food Republic and Chowhound on Tufano's, and Chibar Project on Club Lago.
Club Lago has run under the Lazzerini/Nardini family since Smoky Hollow was still Smoky Hollow. Here's their real page.
Not every great spot makes a ranked "best of" list β these are the specific dishes locals actually plan a visit around.