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Chicago Gangster And Ghost Tour

Know More About This Tour

Chicago Gangsters & Ghosts TOUR

The area most associated with gangster era crime and haunting is know as The loop. This was the cities vice district during the roaring 20s and 1930s riddled with speakeasy saloons, secret underground tunnels used by bootleggers and the headquarters O|hare international airportf famous gangsters such as Al Capone. Guests O|hare international airportf the tour will have the rare O|hare international airportpportunity to visit some O|hare international airportf these famous haunted locations and old crime scenes throughout Chicagos downtown. Places like the haunted Congress Hotel, Death Alley and the Palmer house will all be visited along this tour. Bring your camera because you never know when you might see a ghost!

This tour is guided by a Historian. It is not theatrical, but rather the tales are told in a more around the campfire fashion. Spooky and verified ghost stories will be shared throughout the tour along with visiting the famous gangster hang outs.

Tour Length and Distance

This is a 2 2.5 hour walking tour through The loop area of the citys downtown district. The tour is about 1.5 miles long with frequents stops and a refreshment/restroom break.

Tour Time and Meeting Location

The tour meets at 8 p.m. nightly next to the Wyndham Grand Riverfront Hotel at 73 E. Upper Wacker Drive on the corner of Wacker Drive and N. Wabash.

Exploring Chicagos 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.

Chicagos 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 citys 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.

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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 Chicagos gangster history.

Exploring Chicagos 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 Americas 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.

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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.

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Current Tours From Weird Chicago

DEVIL AND THE WHITE CITY BUS TOURS CHICAGO’S FIRST H.H. HOLMES TOUR!Created by Weird Chicago in 2006 , this is the original tour that delves into the history, mystery, murder and mayhem of the American serial killer, H.H. Holmes and the Worlds Columbian Exposition in Chicago in 1893. During the Worlds Fair, Holmes operated the infamous Murder Castle and this was the first tour to take you on a journey back in time to not only the places where Holmes sought out and dispatched his victims, but also to take a look at the remnants of the spectacular fair and to get an inside look at Chicago in 1893 and what the world saw when it came to the Windy City! Experience it with the company that started it all!$42 for Adults | $32 for Kids


Our acclaimed tour of ghosts, gangsters, mystery, the macabre, and everything else that makes our tour so great and has earned us so many fantastic reviews! Join us and experience Chicagos many ghosts, haunted history, and all around strangeness! We dont just drive past Chicagos spooky places, we let you experience them first-hand! Often imitated, but never equaled, its a tour of the Windy City that you wont soon forget!

* 3 Hours of Weird Chicago History & Hauntings at the Citys Spookiest Locations!* On and Off the Bus throughout the evening* Based on More 25 Years of Research and Writing

$42 for Adults | $32 for Kids


Brief History Of Chicago

Gangsters and Ghosts Tour in Chicago from $27

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.


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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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Types Of Gangsters And Ghost Tours

Offering a non-theatrical crime tour that encompasses approximately 1 ½ miles, Gangsters and Ghosts Tours are focused on the thing that they know bestChicagos dark and ominous history. Tours are hosted by knowledgeable historians who share stories to paint a picture of the sinister world of the windy citys past. Spooky tales of gangsters and ghosts along the streets and in the buildings of Chicago are told as the tour group stops at famous locations in the Chicago Loop Vice District.

Gangsters And Ghosts Tour In Chicago

  • Learn more
  • Instant confirmation
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
  • Insightful commentary shared by the guide
  • Mixture of historical fact and ghost stories makes for a fun tour
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.
  • Insightful commentary shared by the guide
  • Mixture of historical fact and ghost stories makes for a fun tour
  • Walking tour of Chicagos gangsters and ghost stories
  • 71 E Wacker Dr, Chicago, IL 60601, USAThe tour meets outside under the “Hoyt’s” sign in front of Hoyt’s Restaurant at The Wyndham Grand Riverfront Hotel.
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Near public transportation
  • Travelers should have a moderate physical fitness level
  • This experience requires good weather. If its canceled due to poor weather, youll be offered a different date or a full refund
  • This tour/activity will have a maximum of 20 travelers
  • Walking tour of Chicagos gangsters and ghost stories
  • Gratuities
  • 71 E Wacker Dr, Chicago, IL 60601, USAThe tour meets outside under the “Hoyt’s” sign in front of Hoyt’s Restaurant at The Wyndham Grand Riverfront Hotel.
  • 520 S Michigan Ave, Chicago, IL 60605, USA
  • Regular temperature checks for staff
  • Contactless payment for gratuities and add-ons
  • Face masks required for guides in public areas

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Explore Chicago From A Different Perspective With The Gangster And Ghosts Tour

Get a close look at the #1 Gangster and Ghost Tours in Chicago!

For those who are interested in exploring Chicago from a different perspective a mix of ghosts and gangsters, this is a unique experience worth trying out during your stay in Chicago. Learn about the history of this distinguished American city on the places that started it all.

Enjoy the cream of the crop of both worlds with the 2 in 1, a history-based tour with a guide where you will learn about Chicagos gangsters and ghost stories, starting from the well-known Chicago Loop Vice District.

Where To Begin To Explore Chicago’s Seedy Side

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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.

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Weird Chicago Tours General Information

H.H. Holmes from Weird Chicagos The Devil & the White City Tour

  • See the public tour schedule above or arrange a private tour for your group! All Reservations made online!

  • The Weird Chicago Bus Tours run about 3 hours in length. We travel all over the city and we do get on and off the bus throughout the tour. We use air-conditioned and heated buses, but are frequently off the bus, so be sure to dress for the weather! We do not offer an itinerary or list of stops for the tour. It can sometimes change and sadly, other companies copy our tours so wed rather keep that info to ourselves and share it with our guests during the tour! Just come expecting the unexpected and you’ll be glad you did!

  • All tours take place rain or shine. We do get off the bus. If it’s raining, bring an umbrella. We don’t cancel because of weather . Dress according to the temperature and conditions!

  • This is also the case for walking tours we offer the tour even if it rains and ask you to bring an umbrella.

  • Children over the age of 10 are welcome on the tours, but its not recommended for kids under the age of 10. Sorry, no babies or infants in strollers on bus tours. No one under the age of 21 is allowed on our pub crawls or the Roaring 20s Tour when operating.

  • Our walking tours are offered for people of all ages, including children. We do have one pub stop on the walking tour but it is family-friendly.

Gangsters And Ghosts Tours

As we mentioned in previous sections, some tours focus on both the dark and twisted stories from Chicagos criminal history and reported hauntings that have taken place in the city.

If youre interested in learning about both subjects while youre exploring Chicago, these tours provide an excellent opportunity to discover a side of the windy city that some visitors never get to see.

One popular option is a 2-hour walking tour which includes stops at several notable locations in the Chicago Loop such as the Congress Hotel, the Palmer House, and Death Alley.

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Gangsters And Ghost Tours Considerations

Answers to questions you might have before taking aGangsters and Ghosts Tour:

  • Cameras are not only allowed, but arerecommendedbecause you never know when you might see a ghost!
  • Tours are family friendly and make frequentstops for restrooms and refreshment breaks
  • Children of any age are welcome and may receivediscounted tickets. Children under the age of 6 years old may be complementary.
  • Meeting location is typically at Wyndham GrandRiverfront Hotel, 71 E Upper Wacker Drive .
  • This 1 ½ mile tour encompasses a fair amount ofwalking. Participants should wear comfortable walking shoes.
  • Tours run rain-or-shine which means that guestsshould dress appropriately for the weather, bringing a sweater or jacket alongduring cooler months.
  • For an added amount of spooky fun, choose anevening tour when its dark outside!
  • Unfortunately, Gangsters and Ghosts tours arenot wheelchair accessible due to the nature of the locations visited.
  • This tour typically hosts a group ofapproximately 15 people, making it small and intimate.
  • Refunds of booked tickets may be possible 24hours or more prior to the start date of the experience.
  • Tours tend to sell out, especially during summermonths, so be sure to book tickets well in advance of your preferred day.
  • These tours typically end in a different placethan where they began. Guests should be sure they understand how to return totheir car or hotel from the ending location. Guides are happy to help with thisinformation.

What Youll See On A Gangsters And Ghost Tour

Haunted Journeys

Exploring the Chicago Loop Vice District, Gangsters and Ghosts tour groups typically meet at the Wyndham Grand Riverfront Hotel and spend time walking throughout the local area. The district got its name during the 20s and 30s when the area was riddled with speakeasy saloons, secret underground tunnels and shady deal-making.

Guests of the tour will visit various crimes scenes andhaunted locations where all kinds of infamous activities happened a centuryago, including:

  • The Congress Hotelconstructed in 1893, the visitation site of the ghost of Dr. Henry H. Holmes, Chicagos first serial murderer
  • Death Alleyalso known as Couch Place, this location is where more than 600 people fell or were trampled to death as they tried to escape a fire in the theater next door
  • Palmer Houseiconic for its importance during days of big bands and jazz starlets
  • Chicago Athletic Associationjust down the street from Al Capones former headquarters
  • Gangsters and Ghosts Tours typically end at the Congress Hotel

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Chicago Gangsters And Ghosts Tour Tickets Prices What To Expect

This Gangsters and Ghosts Tour in Chicago is a two-in-one tour where you learn the citys history and also about its underbelly.

It is a history-based guided tour of Chicagos gangsters and ghost stories, right in the famous Chicago Loop Vice District.

A historian takes you around the citys important landmarks and helps you travel back in time to the Roaring Twenties when the Chicago Loop was a hotbed for bootleggers, speakeasies, and gangsters like Al Capone.

As part of the Ghosts and Gangsters tour of Chicago, you will also visit the Palmer House, Congress Hotel, and Death Alley, which were all once gangster hangouts.

Book A Gangsters And Ghost Tour

Tickets for Gangsters and Ghost Tours should be purchased in advance online. Tours often sell out. Booking with is easy online. Online bookings show weekly availability including tour times as well as revealing tours that are already sold out. Pay for your tour in advance with a credit card and receive an email with all of the information you need about where and when tours meet as well as what to expect.

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Tours Start At Just $72

If you are looking for fun things to do in Chicago at night, why not try one of our Chicago haunted ghost tours? Join Absolutely Chicago Segway Tours on this haunted segway tour of Chicago where we share Chicago’s history of death, disasters, murder, infamous gangsters, and ghostly tales. You will glide around the streets of downtown Chicago, escorted by one of our Segway tour guides. Eerily, we creep through the shadows and darkness to hear some of Chicago’s true ghost stories and view the site where some of Chicago’s most appalling disasters took place.

We begin this Haunted Segway Tour of Chicago at our location and glide our segways through the dark paths of the park. We make a stop at Buckingham Fountain, situated between Lake Michigan and Michigan Avenue, to view it in all its lighted glory. Here your guide will share stories of Al Capone’s haunted yacht, and the famous Chicago gangster’s affiliation with a notorious Michigan Avenue hotelallegedly the most haunted hotel in the city. You will learn about the creepy things that have happened in the hotel, such as a number of unexplainable deaths and the self playing piano in the grand ballroom.

This haunted tour of Chicago is a fun thing to do in Chicago in a creepy sort of way!

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