Gangsters & Ghosts: Explore the seedy side of Chicago

The city of Chicago is full of history, culture and music, and like any other great city in the world, Chicago has a past filled with so many sad times. From gangster rivalries to haunted locations, here’s a look at the seedy side of the big city of Chicago and why it’s worth exploring.

Brief history of Chicago

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


It wouldn’t be long before this growing city experienced one of the saddest times in its history. It was in 1871 when a fire destroyed up to 18,000 people and resulted in the death of 300 people.

Soon, the city became a place of music, bustling saloons, and politics, as well as violent racial conflict, gambling, and extreme pollution. Much of this history filled with good and bad characteristics is what makes the city of Chicago known to the world today, and visitors can get a glimpse of this city by embarking on a tour.

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Where to start 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 many museums in the city and read about history, but this method of exploration is limited because one does not have to visit the sites where certain historical events took place. This is why joining a tour is important, as it helps to verbally tell the history of the city to visitors while taking them to the historical sites of the city. When exploring Chicago’s history, an interesting place to start is the city’s gangster era, as it was one of the most interesting.

Related: Chicago’s Old Town 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 quickly became a haven for gangsters, and much of the history of this dark side of the city can still be experienced. today from the tales, sites, people, and all things associated with this gangster era of the city.

The history of Chicago gangsters dates back to 1920, when the illegalization of the consumption, manufacture and sale of alcohol was enacted in the United States. Before that time, different groups of gangsters already controlled different parts of the city. With the illegalization of one of the city’s most beloved drinks, the gangs saw an opportunity to make money by smuggling the goods. Names such as the Al Capone Chicago Outfit, the North Side Gang and the Genna Brothers became popular during this time as they were key players in this business and the crimes and murders that took place over the years following.

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

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

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Related: Explore Chicago’s mysterious tunnel system with this tour

Exploring Chicago Murder Cases

The many deaths that have occurred in Chicago have turned the city into a city of ghosts and hauntings. Most of the sites that now seem normal were places of gruesome murders by serial killers and gangsters.

Murder Castle is one of the popular haunted sites associated with mass murder in Chicago. The history surrounding this castle can be traced to the first American serial killer, a man who took the name – HH Holmes, actively operated in Chicago and oversaw the murder of 27 people, including two of his daughters, according to his confession . This number remains one of the talking points to this day as some sources claim he oversaw the killing of up to 200 people while others claim he only murdered nine people.

His most popular assignment was said to have been at the World’s Fair in Chicago when he lured people to a place he advertised as a hotel with comfortable rooms. With visitors coming to Chicago from all over the country for the event, HH Holmes managed to bring a few to the said hotel. These visitors never came out and the details that follow are gruesome. While the original building was destroyed in 1938, the site can still be visited today, which now houses 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 Chicago gangster and ghost tour, all of the city’s gangster and ghost history will be explained in detail, and one will also be taken to various sites such as Palmer House, the Congress Hall , the Loop and Death Alley, where some of the city’s most heinous crimes have taken place.

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