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Gangster Tour – A Bang Up Time in Chicago

Chicago used to be a gangsters’ haven. They used to be synonymous. Inseparable. They defined each other. But, gone were the days of gang violence and mobster mentality. Chicago cleaned up its act and whoever messes with it now will answer to the law–and not to some sketchy humanoid who claims jurisdiction under his belt.

Chicago’s Prohibition Era has produced notorious mobsters, like Dion O Banion, Earl “Hymie” Weiss, George “Bugs” Moran, Diamond Jim Colosimo, Johnny Torrio, “Machine Gun” Jack McGurn, Eliot Ness and the most famous of them all–Mr. Al Capone who was known as “Scarface”. These names made Chicago infamous by terrorizing residents with their bloody war and struggle of prestige and power.

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Welcome to Chicago’s Gangster Tour!

Also known as Untouchable Tours, this jaunt brings you down the memory lane in Chicago’s gangland past. Nobody is proud about it and no museum in the city revere mementos from these legendary Mafiosos! Many of the places that were frequented by these gangsters were torn down and gone along with city’s wind. This tour brings the Prohibition Era alive with factual history, sound effects, music and anecdotes.

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

Untouchable / Gangster Tour – A Bang Up Time in Chicago.

The tour bus itself was designed like some mobster owns it. It’s black and filled with bullet hole stickers like the transport has just been rained to death in real bullets!

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

Untouchable / Gangster Tour – A Bang Up Time in Chicago.

Dressed in neatly-pressed shirt, black pants with a suspender, a black mafia fedora and tie with a machine gun clip, our pair of tour guides acted and dressed up like they’re one of those kins of Vito Corleone, The Godfather. One is younger than the other but together, they make you believe you are held hostage for two hours in their bus. Our tour started with the younger guy showing off his pistol (probably his toy) to intimidate us or perhaps to establish relationship by telling us he’s in-charge and whether we like it or not, we’re gonna follow his orders. Well-done.

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

Holy Name Cathedral. Two well-known gang leaders were gunned down here: Dion O’ Banion and Hymie Weiss

They each took turn in driving the bus and narrating stories of people and places. When our bus was parked, both of them would exchange banters and argue like no one is inferior to the other. Truly, a mobster’s attitude.

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

This is the backside of the Room 21 where Al Capone used to hangout with his pals. / Untouchable / Gangster Tour – A Bang Up Time in Chicago.

Every time we passed by a place where a murder happened, we would hear a loud and almost surreal sounds of machine guns pounding our bus to shards.  Our gang leaders slash guides would shout and order us to duck in! It’s funny that we  actually them and some of us ducked behind the seats in front of us! Those recorded machine gun sounds are unmistakably scarier than an action movie. You will be caught up by their acts, sound effects and even the blues music they’re playing when they’re not talking.

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

Around this area is the scene of the Valentine’s Day Massacre as masterminded by Al Capone. Seven members of Bugs Moran gang were gunned down here by uniformed policemen. Amazingly, one guy shot with 21 bullets was barely alive to tell the story.

The tour snaked through downtown traffic to three the three major areas where gangsterism was a way of life in the Prohibition Era: North, South and the West sides. We passed by / stopped at places where crime happened and where the gangsters used to live, hang out, shot to death and buried.

Untouchable / Gangster Tour - A Bang Up Time in Chicago.

The “lady in red”, Anna Sage, came to Biograph Theater to accompany his roommate whose boyfriend was FBI’s very first Public Enemy #1, John Dillinger, a notorious bank robber. She was about to be deported back to Romania and in order to avoid it, she agreed to set Dillinger up. In a dark alley, Dillinger was gunned down by the FBI.

I don’t wanna go into details but you have to join it to understand and learn more about Chicago behind and beyond those towering skyscrapers you see all day. Call it real education you can’t get from your history teacher in a four-walled classroom. And believe me, history has never been this fun!

Behind our mobster tour guides’ demeanor are kind hearts. Before the tour ended, they gave us a treat: a pencil and a raffle draw that three winners brought home a gangster’s mug, a book and magnetic bullet holes. They sell these stuff, too.

Reservation for the tour is required. Check the price and schedule here.

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