The City of Chicago is full of history, culture, and music, and just like any other great city around the world, Chicago has a past that is filled with so many sad moments. From gangster rivalries to haunted spots, here’s a look into the seedy side of the great city of Chicago and why it is worth exploring.

Brief History of Chicago

The history of the city of Chicago stretches back to the 17th century when different groups of people, from missionaries to French explorers, made their way to the shores of what is now known as the United States, although the beginning of the modern city known to the world today began in the 1830s when the area was incorporated as a town in 1833 and then a city in 1837. Its incorporation into a city was due to the major role it played in the transportation network and food production in the country. With business continuing in the area, development came to the area swiftly, as did the arrival of African American immigrants, Mexicans, Puerto Ricans, and many other groups of people from different parts of the world.


It would not be long before this growing city experienced one of its saddest moments in history. This was 1871 when a fire disaster destroyed up to 18,000 people and led to the death of 300 people.

Soon the city became a place of music, vibrant saloons, and politics, as well as violent racial conflicts, gambling, and extreme pollution. Much of this history filled with good and bad characteristics is what makes up the city of Chicago known to the world today, and those visiting can take a peek at this city by engaging on tour.

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Where To Begin To Explore Chicago's Seedy Side

There are many ways to explore the history of the city of Chicago. One can visit one of the numerous museums in the city and read about the history, but this exploration method is limited as it does not take one to visit the sites where some historic occurrences took place. This is why it's important to join a tour, as it ensures guests are told the history of the city verbally while being taken to the historic sites around the city. When exploring Chicago's history, one interesting place to start is the gangster era of the city, as it was one of the most interesting.

Related: Old Town Chicago Still Exists, Here's What To Expect There

Exploring Chicago’s Gangster History

As gambling and other illegal activities such as prostitution took over the city of Chicago, it soon became a gangster haven, and much of the history of this dark side of the city can still be experienced today from the tales, the sites, the people, and all things associated with this gangster era of the city.

Chicago’s gangster history can be traced to 1920, when the illegalization of alcohol consumption, manufacture, and the sale was signed into law in the United States. Before that time, different gangster groups were already in control of different parts of the city. With the illegalization of one of the city’s most beloved beverages, gangs saw an opportunity to make money by smuggling the products. Names such as Al Capone Chicago outfit, the North Side Gang, and the Genna brothers became popular during this period as they were key players in this business and the subsequent crimes and murders that took place over the following years.

Soon the city began experiencing gangster-related wars and terrible deaths. Hundreds of gangsters were murdered, shops that refused to purchase alcohol from groups were being bombed, and massacres were ordered.

Visitors to the city today can still see some sites where gangster-related crimes, wars, and deaths occurred. Gangsters and Ghost Tour in Chicago is the perfect tour to take for this experience as it takes visitors to the most popular sites from Chicago’s gangster history.

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Related: Explore Chicago's Mysterious Tunnel System With This Tour

Exploring Chicago’s Murder Cases

The numerous deaths that occurred in Chicago have made the city one of ghosts and haunted sites. Most sites that now seem normal were locations for some horrific murders committed by serial killers and gangsters.

The Murder Castle is one of the popular haunted sites associated with mass murder in Chicago. The story surrounding this castle can be traced to America’s first serial killer, a man who took the name - H.H Holmes, actively operated in Chicago and oversaw the murder of 27 people, including two of his daughters, according to his confessions. This number remains one of discussion to this day as some sources claim he oversaw the murder of up to 200 individuals while others claim he only murdered nine people.

His most popular mission is said to have been carried out during the Chicago World Fair when he lured people into a place he touted as a hotel with comfortable rooms. With visitors coming to Chicago from all over the country for the event, H.H. Holmes succeeded in taking some to the said hotel. Those visitors never came out, and the details that follow are gruesome. While the original building was destroyed in 1938, one can still visit the site today, which now hosts the Englewood Post Office.

There are other interesting murder cases in Chicago, and many of them left traces that can still be found today. On a Gangsters and Ghost Tour in Chicago, all the Gangster and ghost history of the city will be explained in detail, and one will also be taken to various sites such as Palmer House, Congress hotel, the Loop, and Death Alley, where some of the city's most heinous crimes took place.

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