Crime Tour of Chicago

Chicago is a beautiful city, but you’re about to see its dark side. If you have some time, visit Cloud Gate, a reflective sculpture downtown. That’s its name, but all the locals call it The Bean because of its shape.

Your first day is all about Al Capone. You’ll be traveling to the site of the Saint Valentine’s Day Massacre, a murder of seven members and affiliates of the North Side Gang. Although it’s never been confirmed, it is strongly suspected that Capone took out this hit. You’ll see the area where this massacre took place and learn more about Capone and the mob culture during this time period.

Next, head over to the Green Mill Tavern, one of Capone’s favorite spots in the city. You’ll sit in Capone’s regular booth and hear the story of the tunnels located under the building that helped the mobsters carry out their work.

Today, you’ll visit the Richard Speck murder site. In this townhouse, Speck murdered eight student nurses in a grisly fashion. You’ll learn more about the trial and his fate. Next, it’s time to visit the Biograph Theater. Famous mobster John Dillinger was shot to death here in an ambush after watching a movie. Tourists pour out a beer over the exact spot where Dillinger fell after the bullets hit him, and you’ll have the opportunity to pour one out for him too.

John Wayne Gacy is one of America’s most notorious serial killers, and his horrific acts were committed right outside Chicago. You’ll head to the suburbs to see the house where authorities found 26 bodies in a crawl space under his house. Your guide will tell you more about the crimes and Gacy’s history as the Killer Clown. Next, you’ll visit the spot where he gave his first confession to his attorney.

After hearing about so much bad stuff that’s happened in the world, it’s time to do something good! Gun violence was prevalent in the time of the mobsters, but it’s still shockingly common today. You’ll work with an organization in the city that works to help end gun violence and keep the community safe.

Your first stop is a Walgreens in Elmhurst. This stop might seem a bit unusual, but this was the store where a bottle of poisoned Tylenol was purchased in 1982. In total, seven people died, and the crime has still not been solved to this day. Your guide will tell you about the hysteria these murders brought on and how they have changed American packaging laws today.

Tonight, it’s time for a little fun! You’ll head to The Green Door Tavern, another hot spot for Chicago gangsters. But we’re here for what’s in the basement: the room that housed a speakeasy in the 1920s. Lucky for you, there’s still an operating speakeasy here today! You’ll enjoy the atmosphere that these gangsters did, including entertainment like belly dancers and burlesque artists.

It’s time for the Devil in the White City: H.H. Holmes. Some estimate that Holmes murdered at least 200 people using his hotel, often called the “Murder Castle.” You’ll head to the site of the infamous castle. Although the building no longer stands, you can poke around, and your tour guide will tell you all about Holme’s crimes.

Now you’ll go to the Museum of Science & Industry, perhaps not seemingly a crime-heavy location, but it’s actually an original building from the 1893 World’s Fair, where Holmes found more victims and which he used to cover his tracks. Afterward, feel free to check out the museum!

You’ll leave Chicago today, but you’ll have some stories to tell about the city. Maybe some of them will even keep you up at night.