Day 3: Chicago, having fun with history…

With only one day to visit Chicago, it would be impossible to really discover much or even get a “feel” for the character of the city (read more on planning one day visits). We decided not to try. We would explore a theme instead. Considering a multitude of choices, we settled on being a bit playful and searched out the city’s roaring 20s gangster-era lore.

Now, like every town, Chicago works hard to promote the positive — the beautiful, the artistic, the intellectual and cultural things their amazing city has to offer — so there is no official “Gangland Museum” or anything of the sort. In fact, in the 1980s, city officials even blocked an effort to designate Al Capone’s house on the South Side a national historic landmark. However, despite the tourism board’s best efforts, we were not alone in being attracted to this less savory side of their city’s past. Each year thousands of visitors search out the sites on their own. And thanks to some creative entrepreneurial folks, there are now a number of amusing attractions around the “Prohibition-era Chicago” theme.

For some light-hearted fun, we chose to take “The Untouchables” bus tour of Chicago’s gangster highlights, followed by dinner and a show at “Tommy Gun’s Garage,” a roaring twenties spectacle in a “speakeasy” on the site of one of Capone’s old hideouts.


The Untouchables tour bus — a rickety repainted school bus decorated with fake bullet holes — picked us up outside the Rock n Roll McDonalds. Music recorded from scratchy old vinyl records played softly in the background as the costumed tour-guide-actors introduced themselves.

The bus was fairly full. It seems the 1920s era “gangsters” continue to fascinate folks. Despite the carnage they were responsible for as the heads of violent criminal organizations, these larger than life characters are often viewed quite sympathetically.

Thinking about that irony, we realize how many of the popular heroes in American culture were outlaws of one kind or another. Maybe identifying with the “bad guys” is part of some kind of residual anti-government feeling that seems stronger the further west we go. Often the outlaws were seen as “common people” or “folks like us” who had suffered some kind of injustice at the hands of “the government” or “the banks” (this historical trend may still be driving us — think about the foreclosure crisis and the “Tea Party” with their common cry of “government out”).

In any case, the Chicago gangsters’ popularity is most certainly linked to the unique ambiance of the whole “prohibition” debacle — one of the most famous examples of the government going too far in its attempts to legislate morality.

The effort to make the United States ‘dry’ had never found great favor in Chicago, a city with large immigrant populations from cultures — like the Germans and Irish — where drinking alcohol was a part of daily life. Chicago citizens had voted six to one against the nationwide enactment of Prohibition in 1920. When the 18th Amendment became law anyway — banning the sale, transportation and manufacture of alcohol anywhere in America — millions of citizens refused to respect it. In Chicago, as elsewhere, competing gangsters stepped in to supply a huge thirsty market through a network of “speakeasies” around the city. The most famous Chicago mobster, Al Capone, built his reputation by intimidating rivals to give up their territories, eventually running an operation that earned $60 million dollars a year from alcohol sales alone.

Driving around modern-day Chicago there are few actual reminders of this period, but our narrators breathed life into this slice of history, pointing out key locations, and explaining the events that transformed criminals like Capone into folk heroes.

The key to enjoying the tour was to play along with the guides, by reacting to the sound of machine gun fire, and generally cooperating in maintaining the ambiance. The group on our bus did a pretty good job of it, and the drive was an amusing orientation to the geography of the city. Certainly much better than any of your standard city bus tours.


We continued with the roaring twenties fun into the evening, finding our way to Tommy Gun’s Garage, a dinner-theatre venue on the South Side of the city.

After a subway ride and a short stroll through the neighborhood, we were outside the door negotiating our way into the “speakeasy” with a guy dressed in 1920s-style clothing sporting a fedora and a Thompson sub-machine gun. Luckily we had the “password” and he ushered us into the fabulously decorated replica of a prohibition-era “gin joint.”

We were in for an amusing step back into the 1920s booze-running gun-toting Chicago gangster days, on the actual spot of (or right next door to) one of Capone’s real-life hangouts.

A girl, in full flapper regalia, came to take our order, as “Deuce,” one of the mobsters, handed “Silly Squirrel” a bullet (from the blanks they fire out of those Tommy Guns during the show) and took him over to the corner of the “garage” to check out a shiny black Model “A” Ford with running boards.

After dinner the actual show began, with the “staff” performing a “nightclub” parody full of song and dance and comedy. The laughs were only slightly interrupted by a “police raid” which required quite a bit of audience participation. Luckily the crowd was fun-loving and played their parts well, making the show a “hit.” We all had a “blast” (puns intended) and left in “high spirits” (bad pun intended again)!!!



More from Illinois:
NOTES FROM THE ROAD: Chicago, A First Taste… | Chicago Explorations…
AMERICA THE BEAUTIFUL: Portfolio: On the Road to Chicago | Portfolio: Chicago — The City | Portfolio: Chicago Gangster Fun
PRACTICAL MATTERS: Planning One Day in a City
REFLECTIONS & OTHER THINGS: Fragments from the Road to Chicago| Review: The Untouchables Gangster Tour, Chicago | Review: Tommy Gun’s Garage, Chicago

Back to Indiana | Complete Trip Log | Start at the Beginning

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