Chicago | An Untouchables Mobster Tour of the Windy City

Untouchables Bus

He waved a gun at the entire bus while yelling, “Shut up, everybody!” Then he grinned and said, “That’s how you say ‘hello’ in Chicago.” The gun was fake, as was his “gangster” accent, but he stayed in character for the whole bus ride. He was “Baby Face Bambino,” the bus driver was “Shoulders”, and I was there for “Chicago’s Original Gangster Tour” with Untouchable Tours.

Untouchables Tour Guide

If you can get past your views on guns and violence, which I had to do, the history of the mob in Chicago is truly fascinating. It’s understandable that some of the greatest movies of our time are based upon this era. Untouchables Tours take a light-hearted approach to a time period that actually isn’t too far back in time. I consider recent history anything that my grandmother was old enough to remember – granted, she’s a spry 97-year-old, but still.

While we were on a bus, riding around different neighborhoods around town, to me, the tour was more about the stories than of the places we visited. We did pass some notable places where things had happened, but it wasn’t about what the spots looked like – in fact, some had been shut down or changed completely.

Holy Name Cathedral

Early on, we passed by the Holy Name Cathedral downtown which still had a visible bullet hole above the steps where mobster leader of the North Side Gang Hymie Weiss had been gunned down in 1926. The former leader of the gang, Dion O’Banion, had been murdered two years prior to that in his own flower shop (actually a front for a sneakier business) across the way. Later toward the end of the tour, we passed by the now-parking-lot where the famous St. Valentine’s Day massacre took place, which resulted in the loss of five members of the North Side Irish Gang and two “affiliates”. The massacre is thought to have been ordered by the infamous Al Capone, head of the South Side Italian Gang. It did feel a little odd to me that we were passing by places where people had been murdered, but I may have been the only one on the bus with that in mind.

Biograph Theater

Not every site we rode by was somewhere something awful took place, though the Biograph Theater above was. We took a ride through Chicago’s Little Italy as the Godfather theme (or as Baby Face Bambino called it, “The Italian National Anthem”) played on the radio, hearing tales of the Genna Brothers, six Sicilian brothers in the business of bootlegging. We passed the Hilton Chicago, which used to be the Stevens hotel – then the largest hotel in the world – which charged a whole $10 a night for the presidential suite. It’s on the tour because it’s of the time period, but also because Al Capone kind of, maybe, definitely forced jazz singer Fats WallerΒ to perform in Capone’s suite at the hotel when Fats came to Chicago. Fats did get $10,000 out of the deal if you can call it that.

6 of Spades

Though he was known to everyone as Scarface, you couldn’t have Al Capone catch you calling him that. He much preferred other nicknames like, surprisingly, “Snorky” – an indication that he was breathing better air than others, as if, yes, by using a snorkel. (Wikipedia calls “Snorky” a term for a sharp dresser back in the day – choose whichever explanation you like.) If you were close to him, you could call him “The Big Guy” or “Big Al”. I think I would have stuck with “Sir”. For such a sinister man, it still surprises me that what he was put away for was tax evasion, above everything else he was responsible for, and that he died of complications with syphilis instead of at the hands of his many enemies.

Untouchables Bus

The tour not only provides the history of the times in Chicago, but touches upon things that were going on nationally at the same time. I learned that the term “bootleggers” came from when people would hide flasks of liquor in their bootstraps during prohibition. The term “moonshine” was coined because it was a liquor created at night, by the light of the moon. The few times we were in transit without a story, we were treated to sweet tunes like “Lulu’s Back in Town“, “Minnie the Moocher“, and “Happy Feet“.

It was certainly an educational experience about another side of the Windy City, one that you wouldn’t even suspect if you were just wandering the town in search of your next slice of deep dish or cheering on the Cubs at Wrigley. Another thing the tour did for me was finally inspire me to watch the Godfather. It was about time.

Who might the Untouchables Tour be good for?

  • Adults
  • Older teenagers (Untouchables Tours recommends high school age and older)
  • History buffs
  • Chicago visitors and residents
  • People wanting to get out of the rain or cold (you remain on the bus for entire tour)

Who might find the Untouchables Tour challenging?

  • Kids (Untouchables Tours recommends high school age and older)
  • People who are sensitive about guns, violence, and death
  • People who want to take photographs (you remain on the bus for entire tour)
  • Non-English speakers


Have you been to Chicago?

What was your favorite activity there?



Many thanks to Untouchable Tours for hosting me on this tour – $35 at the time of this post. Opinions are always my own.

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