Why Is Chicago Called ‘Shy Town’?

Chicago is famously called the ‘Windy City,’ but some also know it by another nickname – ‘Shy Town.’ At first glance, shy doesn’t seem to fit with a bustling metropolis like Chicago. So why the odd moniker? If you’re short on time, here’s the quick answer: ‘Shy Town’ refers to Chicago’s days as a center of illegal activity and mobsters in the 1920s-1930s. Shy is slang from this era meaning on the sly, illegal activities.

In this comprehensive article, we’ll dive into the full story behind Chicago’s ‘Shy Town’ nickname. We’ll explore the Prohibition era roots when shy gained popularity. We’ll also look at how Chicago’s underground economy and corruption led to this nickname taking hold in the city’s lexicon.

Origins in Prohibition Era Slang

Chicago, famously known as the “Windy City,” has another nickname that has intrigued both locals and visitors for decades – “Shy Town.” The origins of this nickname can be traced back to the Prohibition era in the United States, which lasted from 1920 to 1933.

During this time, the production, sale, and distribution of alcoholic beverages were banned. However, Chicago became notorious for its thriving underground speakeasies and illegal alcohol trade.

Rise of Slang Term ‘Shy’

One theory suggests that the term “Shy” originated from the slang word “shylock,” which referred to a person who lent money at extremely high-interest rates. In the context of the Prohibition era, “shy” was used as a code word to describe the illegal alcohol being sold in Chicago.

The term was likely used to avoid drawing attention from law enforcement or others who may be listening.

Another theory suggests that “Shy” was a shortened version of the word “shyster,” which was a derogatory term used to describe a dishonest or unscrupulous person. This term was often associated with bootleggers and those involved in the illegal alcohol trade in Chicago.

Popularity in Chicago Underworld

The term “Shy” gained popularity within the Chicago underworld during the Prohibition era. It became widely used among gangsters, bootleggers, and speakeasy owners to refer to Chicago and its thriving illegal alcohol trade.

The nickname “Shy Town” eventually caught on and became a way for people in the know to refer to the city.

Chicago’s reputation as a city with a flourishing underworld and a disregard for Prohibition laws contributed to the popularity of the nickname. The city became synonymous with illegal activities, and “Shy Town” became a symbol of the defiance and resilience of Chicagoans during this time.

While the exact origin of the term “Shy Town” may remain somewhat uncertain, its association with the Prohibition era and Chicago’s underground activities is undeniable. It has become a part of Chicago’s history and cultural identity, representing a time of rebellion and the city’s unique spirit.

Chicago’s Reputation for Illegal Activity

Chicago, often referred to as the “Windy City,” has another nickname that has been attached to its name for decades – “Shy Town.” This nickname stems from the city’s historical reputation for illegal activities and organized crime.

Let’s delve into some of the reasons why Chicago earned this notorious reputation.

Mobsters and Speakeasies

During the Prohibition era in the 1920s, Chicago became a hotbed for illegal alcohol production and distribution. This led to the rise of notorious mobsters, such as Al Capone, who controlled an extensive criminal empire in the city.

Speakeasies, which were secret bars where people could enjoy alcoholic beverages, flourished in Chicago during this time. The combination of mobsters and speakeasies contributed to the city’s reputation for illegal activity and defiance of the law.

Police Corruption

Another factor that contributed to Chicago’s reputation for illegal activity was widespread police corruption. In the early 20th century, the Chicago Police Department was plagued by corruption and bribery.

Some police officers were on the payroll of mobsters, turning a blind eye to their illegal activities in exchange for financial gain. This corruption further fueled the city’s reputation as a place where the law could be easily manipulated and disregarded.

Legacy of Al Capone

The legacy of Al Capone, one of the most infamous mobsters in American history, also adds to Chicago’s reputation for illegal activity. Capone was the leader of the Chicago Outfit, a powerful and ruthless criminal organization.

His reign of terror included involvement in bootlegging, gambling, and prostitution. Capone’s notoriety and the violent nature of his activities solidified Chicago’s association with organized crime, cementing its reputation as a city where illegal activities thrived.

While Chicago has come a long way from its tumultuous past, the city’s reputation for illegal activity during the prohibition era and the influence of mobsters like Al Capone continue to shape its image.

It’s important to note that Chicago has since made significant strides in combating crime and improving its reputation. Today, it is a vibrant and culturally diverse city that offers a wide range of attractions and opportunities for its residents and visitors.

Use of the Nickname Over the Decades

The nickname “Shy Town” has been used to refer to Chicago for several decades, and its usage has evolved over time. Initially, the nickname was a derogatory term used by outsiders to describe the city’s perceived shyness or timidity.

However, over the years, Chicagoans have embraced the nickname and it has become a symbol of pride and resilience for the city.

In Chicago Newspapers and Media

The nickname “Shy Town” first gained popularity in the early 20th century and was frequently used in Chicago newspapers and media. Journalists and writers often used the term to describe the city’s reserved and humble nature, contrasting it with the bustling and flamboyant image of other major cities.

The nickname became ingrained in the city’s identity and was used as a way to differentiate Chicago from its counterparts.

One of the most well-known uses of the nickname was in the Chicago Tribune, which often referred to the city as “Shy Town” in its headlines and articles. The newspaper played a significant role in popularizing the term and making it known to a wider audience.

References in Pop Culture

Over the years, the nickname “Shy Town” has been referenced in various forms of popular culture, including music, movies, and literature. Musicians like Frank Sinatra and B.B. King have mentioned the nickname in their songs, further cementing its association with Chicago.

In movies and television shows, characters often use the nickname as a shorthand way to refer to the city. It has become a recognizable and iconic reference, instantly evoking images of Chicago and its unique character.

Even in literature, authors have used the nickname to capture the essence of Chicago. In Nelson Algren’s novel “Chicago: City on the Make,” he refers to the city as “Shy Town” to emphasize its gritty and resilient nature.

Persistence of the Moniker Today

Despite its origins as a derogatory term, the nickname “Shy Town” has persisted and remains in use today. It has become a part of Chicago’s cultural lexicon and is often used by locals to affectionately refer to their city.

The nickname embodies the spirit of Chicagoans, who are known for their hardworking and down-to-earth nature. It serves as a reminder of the city’s resilience in the face of challenges and its ability to overcome adversity.

Today, “Shy Town” is often used in a lighthearted and playful manner, showcasing the city’s sense of humor and self-awareness. It has become a badge of honor for Chicago and a symbol of its unique identity.


While not as well known today, ‘Shy Town’ has been a nickname for Chicago for almost a century, calling out the city’s history as a hub for the covert underworld. As this article has shown, the term shy stemmed from Prohibition era slang, but took hold due to Chicago’s open secrets of mobsters, corruption, and illegal enterprises in the early 1900s. The city’s complex past is reflected in this sly nickname.

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