Chicago’s Little Italy

You can’t look at the history of Italians in Chicago and ignore the influence of the mafia. The 1900s saw a wave of Italian immigration that brought with it crime families from Sicily that set up in the south side of Chicago, to be later known as Little Sicily. Chicago became the fountainhead of the underground liquor trade when prohibition drove drinking to secret speakeasys. All of this was arranged by the men smuggling it, Al Capone and his Chicago mafia. Capone became one of the richest men in history taking advantage of prohibition laws and the richest Italian American. The Chicago branch of the mob became so powerful it gained a seat of the Italian Mafia commissioner in America, separate from the original Five Families of New York’s mafia. After Capone’s arrest the mob was handled by even more capable bosses who expanded the influence of the mafia throughout the Midwest, and westward to Las Vegas and Los Angeles. The casinos they ran were given to them by the five families, such was the respect the Chicago syndicate had earned with the senior capos. These men’s influence can’t be overlooked, because still today one of the richest Italian Americans was a billionaire Italian mob boss based in Chicago, by name of John “No Nose” Difronzo. The fact that his name was well known but he continued to run his enterprise until his death in 2018, is a testament to the power Italian families still hold in Chicago.

The gang wars between the Italian Southside and Irish gang-controlled North Sid turned Chicago into a battlefield of shoot outs and public assassinations in the 1920s, creating great prejudice against Irish and Italians in Chicago, who became associated with the criminal elements of the city. Events such as the Valentine’s Day Massacre where Capone had several North Side leaders murdered made the city notorious for gaming violence. The city launched a crackdown on the gangs that did little but arrest Capone for tax evasion and the cause was a change in mob leadership. During Capones time, the 20’s, mob membership reached 1% of the Italian American population. The Italians made up for the prejudice gang violence brought with their fast climb up the ladder. Labor unions, church, and school programs just for Italians were introduced in the early 20th century by Italian Americans to integrate them into American life. Al Capone continued this tradition, making ties with the non-Italian political leaders in Chicago by throwing social fundraisers where he lines people’s pockets and gained a charitable reputation by setting up soup kitchens. Because he played the politician so well, Capone was left alone by the police of the city to build his criminal enterprise. Italians were completely self-sufficient in their communities, they retained the language of their homeland and their sons and daughters married other Italians, and a strong Catholic upbringing was the story for most Italians in Chicago for most of the 20th century. It wasn’t until World War II drafted young Italians to go to Europe and fight other Italians and take down the fascist Mussolini, that they began to lose the tradition of Italian language and began marrying outside Italian families. Neither of these was widespread since the war, but a living Italy existing in Chicago began to fade after the Second World War and a leveling off of Italian immigration to the city.

The Italian neighborhoods started to spread out and disappear aft get the Second World War. It was never publicly stated whether it was on purpose or not, but there seemed to be a concerted effort to break up the Chicago mob by breaking up the Italian community. Benefits for veterans after the war sent a generation of Italians across the country to universities they would not have considered before, the few square miles of the south side had been big enough to never leave. Benefits for Italians not going back to school like housing plans provided enough capital to move into the surrounding suburbs, a move most Italians hadn’t seen as a possibility for the last few generations. Further urban housing plans such as the Cabrini Green housing project leveled Italian homes and began the demographic reorganization of the south side from Italian to the African American community we see there today.

In the ’60s, the building of an interstate highway carved a trench through Italian neighborhoods and leveled one of their iconic Cathedrals, also a school, which served as a meeting place for the Italian community. It would be hard to imagine the city getting away it today in the age of social media, with tearing down a historic cathedral and school for children in order to build a highway, but apparently Chicago was ready for a change after the bloody years of Capone and mob imposed taxes all around Chicago. A real effort seemed underway to drive out the Italian community by cutting it up with highways and literally claiming houses for the state to be torn down and rebuilt for their own purposes. In the 60s, the mayor of Chicago chose to expand the University of Illinois by leveling a square mile of the Little Sicily for development. This move became the death knell for the tight-knit, Italian speaking Catholic community. With their old slice of the homeland thoroughly dissected or erased, they left the city in droves for the suburbs or other cities.

Work Cited

Dickson, Mike. “Chicago Outfit.” American Mafia History,

Candeloro, Dominic. “Historical Research and Narrative.” Chicago’s Italians: Immigrants, Ethnics, Achieveers, 1850-1985,

Christmas time is close in Little Italy.
Early 20th century parades for Italian Americans. Scenes like this were used in the Godfather. The sight of red, green, and red flags alongside the stars and stripes being carried aloft down big city streets is an icon of America.
The great influx of Italians and Greeks led to the influence of Roman and Grecian architecture. Parts of Chicago allude to an age of Grandeur, when the city rivaled New York in economy and size. It also would look to someone who didn’t know the history of America, that this city had been here since the time of the grand Roman Empire.

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