Chicago Crime Tours Review: Why It’s the Best Way to Learn Chicago History

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Chicago Crime Tours Review - Chicago Crime Tours.
Chicago Crime Tours. Photo credit: Adina Keeling

What comes to mind when you hear “Chicago mob history?” If Al Capone is the only name that surfaces, it might be time to dive deeper into this city’s infamous history, especially if you’re a Chicago enthusiast or a local.

I lived in Chicago for four years without ever really knowing what the city’s mob history entailed. And what I did understand about the city’s mobsters was all thanks to the movie, The Untouchables.

So, when I went back to visit Chicago this September, I was determined to learn a little more. To combine a history lesson with a fun ride around the city, I decided to take a bus tour with Chicago Crime Tours and Experiences, a local organization that offers history bus tours.

The company has two different bus tours—a shorter daytime ride and a longer nighttime tour. Both depart from Chicago’s Magnificent Mile and take guests around the city while making stops at several historic locations.

Chicago Crime Tours Review - Boarding the bus.
Boarding the bus. Photo credit: Adina Keeling

Along with a friend, I joined the company’s Night Tour, which lasted a little over two hours and was led by an informed tour guide, John, and a bus driver, Tommy. We stopped three times, watched historic video footage on a large TV inside the climate-controlled bus, and listened as our guide regaled the rivalry between the North Side Gang and the South Side Gang.

Our tour concluded with a little surprise treat: a slice of deep dish that we picked up along the way.

Chicago Crime Tours Review - A brochure passed out before the tour that served as a helpful guide
A brochure passed out before the tour that served as a helpful guide, with photos of key events and historical figures. Photo credit: Adina Keeling

What Does the Tour Cover?

While the tour centers on Chicago gangsters, it also details some of the city’s basic history, such as the meaning behind the city’s flag, the redirecting of the Chicago River, and the Great Chicago Fire. Our guide also spoke about George Wellington Streeter and Elma Lockwood Streeter, described as “Bonnie and Clyde” type figures.

Wondering if Chicago honors its shady past? Chicago’s Streeterville neighborhood is name for George and Elma.

John Dillinger is another important character on the tour. He is an American gangster who robbed 24 banks while garnering a Robin Hood reputation. Dillinger was declared America’s first Public Enemy Number One and was killed in Chicago outside a movie theater.

Most of the tour centers on the infamous South Side Gang, led by Johnny Torrio and Al Capone, and their opponents, the North Side Gang, who gained prominence during prohibition-era Chicago.

Other key events discussed in the tour include the St. Valentine’s Day Massacre and Dean O’Banion’s Assassination. There is also a brief mention of some famous crime stories, such as H. H. Holmes (the serial killer who operated during the World’s Columbian Exposition in 1893 in Chicago) and the Tylenol murders.

Chicago Crime Tours Review - The photo on the bottom left of the brochure shows the site of the Valentine's Day Massacre.
The photo on the bottom left of the brochure shows the site of the Valentine’s Day Massacre. The left side of the photo shows that area today. Photo credit: Adina Keeling

Who Should Take the Chicago Crime Tour?

Chicago Crime Tours are great for history lovers, or anyone hoping to learn more about Chicago. While the tours do tell some true crime stories, none of the descriptions are very gory or vivid, meaning the tour is still appropriate for older children and teens.

The Chicago Crime Tours website specifically recommends the tours for children aged 10 and up. While children under 10 are still welcome to join, they may struggle to follow all the history uncovered on the tour.

When I took the tour, my friend and I were the youngest guests (we’re in our mid-20s); the majority of the other guests were middle-aged or older. That being said, the tour is really for anyone who wants to learn some Chicago history.

Chicago Crime Tours Review - The inside of our bus.
The inside of our bus. Photo credit: Adina Keeling

How Many People Are on Each Tour?

There were approximately 15 people on our tour bus, though there were still plenty of empty seats, so I imagine the tour could have been significantly larger.

How Long is the Chicago Crime Tour?

Our tour was a little over two hours. According to the company’s website, the nighttime tour is usually between 2 and 2.5 hours, while the daytime tour is between 1.5 and 2 hours.

Chicago Crime Tours Review - Harry Caray’s, one of the stops on our tour.
Harry Caray’s, one of the stops on our tour. Photo credit: Adina Keeling

What Does the Tour Stop?

The bus tour I attended made three stops: one at the theater where John Dillinger was killed, the site of the St. Valentine’s Day Massacre, and Harry Caray’s Italian Steakhouse, home to a hidden underground vault used by Frank Nitti, a member of Al Capone’s gang.

What Time is the Tour?

The daytime tours are at 10 a.m., noon, 2 p.m. and 4 p.m. The Night Crimes Tour starts at 7:30 p.m.

Chicago Crime Tours Review - A quote by John Dillinger
A quote by John Dillinger, printed against the side of a building. Photo credit: Adina Keeling

Where Does the Tour Start?

The tour starts and ends outside the Holy Name Cathedral, at 163 E Pearson St.

Is There a Lot of Walking on This Tour?

Nope, this is not a walking tour. Although there are several stops, you can choose to stay on the bus, and none of the stops requires much walking.

Adina Keeling is a freelance travel writer from San Diego, CA. She worked in local news for a year until her wanderlust drew her to Costa Rica, where she is now based while freelancing and traveling the world. She has lived in three different countries and traveled to 27. An avid solo traveler, Adina wants to empower other women to safely travel alone.
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