St. Valentine’s Day 2022 The Chicago Gangster Way!

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Let’s put an interesting twist on St. Valentine’s Day. How about a trip to one of my favorite cities. We lived there for several years and there are some wonderful and fun things to do in Chicago. Let’s think St. Valentine’s Day murders. Yes, I know that it’s a bit dark, ok, a lot dark, but think how memorable and different a weekend like this would be.

Chicago is known for its gang history and more famously for Al Capone. Capone became involved in gangs in New York City and in 1919 after earning the nickname Scarface due ti a knife fight, Capone moved to Chicago where he began his career as a bouncer. He was also a bootlegger, a boxing promoter, right hand man, and negotiator. He became crime boss at the age 26 after the death of Johnny Torrio.

Capone was front and center of the Chicago gang wars and evaded prosecution for years. The Sr. Valentine’s Day MAssacre (February 14, 1929) was a turning point in the fight against gang activity. Herbert Hoover formed an agency, at the behest of the editor of The Chicago Tribune, to fight gang activity in Chicago. Walter Strong felt that the federal government was the only force that could curb Capone and the other mob bosses. The Untouchables were born. There were also legal battles that looked to prosecute bootleggers for not reporting income. This was tested in South Carolina and went to the Supreme Court where it was decided that the 5th amendment did not protect bootleggers for avoiding taxes. The IRS then began investigations.

Al Capone went to  Atlanta U.S. Penitentiary in May 1932 for tax evasion. He was later transferred to Alcatraz Federal Penitentiary in August 1934 for “special treatment”. This came after an investigation that several prisoners were protecting him but there was no special treatment. He was diagnosed with syphilis and gonorrhea along with cocaine withdrawal which caused a perforated nasal septum. His declined proceeded and a formal diagnosis of syphilis of the brain was made in February 1938.

Capone spent his last year in Alcatraz in the hospital wing. He was transferred to  Federal Correctional Institution at Terminal Island to serve his sentence for contempt of court. Capone’s wife, Mae, petitioned the court for early release due to his reduced mental capabilities. He was paroled on November 16, 1939.

Capone attempted to receive treatment for late stage syphilis at Johns Hopkin Hospital in Baltimore but the hospital refused to accept based on his reputation. Union Memorial Hospital accepted him as a patient and he was grateful for the compassionate. He donated to Japanese Weeping Cherry trees as a thank you. In March of 1940, Capone went to Florida for inpatient and outpatient care and was one of the first American patients to receive penicillin. Unfortunately it was too late and the treatment only served to slow the syphilis.

Mt. Carmel Cemetery

Capone spent his lived out his years in his mansion in Palm Island surrounded by his grandchildren and attended to by his wife, Mae. Capone’s physician In 1946, physicians confirmed that his mental capabilities were that of a 12 year old. He had a stroke in January of 1947. After a series of issues, Capone died on January 25, 1947 at the age of 48. His body was transported back to Chicago and was originally buried at Mount Olivet Cemetery. In 1950, Capone’s remains, along with those of his father, Gabriele, and brother, Salvatore, were moved to Mount Carmel Cemetery where he is buried not far from the entrance.

There are other famous Chicago gangsters such as George “Bugs” Moran, Earl “Hymie” Weiss, “Bloody” Angelo Genna, and “Machine Gun” Jack McGurn. McGurn was the inventor of the Tommy Gun. John Dillinger was another infamous Chicago gangster. He died in front of the Biograph Theater after being betrayed by Polly Hamilton the Lady in Red. The Biograph is still open today as a live performance venue.

Places to Stay

Another way to get into the St. Valentine’s Day Chicago mood is where you stay. There are three gang related spots that perfect for your weekend away.

Millennium Knickerbocker Hotel: The Knickerbocker is on Walton Place just off Michigan Avenue in the Magnificent Mile. In 1980, a secret door was found that hid a staircase. The staircase led to a penthouse casino that was reportedly run by Al Capone’s brother. The martini bar serves 1920s cocktails and martinis.

The Pendry Hotel in the Carbine & Carbon Building: The Pendry is on Michigan Avenue near Wacker and is not far from Millenium Park. The building was built in 1929 and it’s art deco style looks like dark green champagne bottle corked with gold foil, which was intentionally designed by the architectects. It is said that this was in response to Prohibition.

Renaissance Blackstone Chicago Hotel: The Blackstone resides on Michigan Avenue near Grant Park and Buckingham Fountain towards the south end. This hotel was the site of the first mob Crime Convention. In 1931, Lucky Luciano hosted the event in the Blackstone’s Crystal Ball where the convention established a board of directors for Luciano’s National Crime Syndicate.

Gangster Tours

I like Viator as an option for finding and booking tours. The site is easy to use and you have an option to pay right away or hold you payment for a later date. This last option may not be a bad idea since I am hearing about cancellations and restrictions. I am worried about my trip to Europe because of the cruise lines are cancelling and one of the cancellations on Norwegian is the day before mine.

I found some interesting tours on Viator.

Chicago Crime and Mob Bus Tour: this is a tour in an air-conditioned bu that takes you to famed spots in Gold Coast, Lincoln Park, Old Town, the Loop and Magnificent Mile

Gangsters and Ghosts Tour in Chicago: A roaring 20s history of gangsters and haunted sites like he Palmer House, Congress Hotel, and Death Alley.

Chicago Night Crimes Bus Tour: This is a 2.5 hour bus tour along sites like the St. Valentine’s Day garage and gangster watering holes like The Burwood Tap and Harry Caray’s Italian Steakhouse.

Private Al Capone Gangster Tour in Chicago: a private tour of all that is Al Capone. You’ll hear about former speakeasies, historic hotels, and crime scenes that Capone and The Untouchables staged their epic battles.

Fore more tours and interesting gang related spots, Frommer’s has put together and excellent list of places to go. Take a peak at Vacations with Capone: Sightseeing Chicago’s Gangster Years.

There are a lot of spots that you can still eat that have ties to 1920s gangland Chicago. Eater has a list of those places: It’s Good To Be A Gangster: 10 Chicago Haunts Where the Mafia Hung Out. The Beverly location of Fox’s Restaurant & Pub was once a deli owned by Al Capone’s sister. The location is out of the way and is south of Hyde Park. Remember to call ahead since some places may be restricted, have altered hours, or are closed.

Chicago Oven Grinders and Pizza


“If buildings could talk, the narrow three-story brick structure at 2121 North Clark Street, Chicago, could tell quite a tale: genteel youth, evil middle age, fiery holocaust — and rebirth.

No one seems to know just when the old house was built, but there are distinct traces of Victorian gentility in its brownstone front, its second-story entrance reached by a flight of stone steps and its high ceilinged, narrow-windowed formality.

If the building ever did possess gentility, though, it was abruptly forsaken on February 14, 1929, as the guttural yammering of submachine guns in a garage almost directly across the street brought the notorious “St. Valentine’s Day Massacre” to headlines around the world. Rumor even has it that the house at 2121 North Clark served as a lookout post for hoodlum henchmen of the Valentine gunners.

The succeeding years were unkind to the old house, as it passed through a series of ever less savory occupancies. Then, in November 1971, came the ultimate indignity: fire. When the ashes cooled, all that remained was a gutted shell of perhaps early glory.

Today, like the phoenix of myth, 2121 North Clark Street has been reborn. Purchased in April 1972 by Chicago attorney Albert H. Beaver, the old house has undergone a year long process of receiving a facelift.

And what a facelift! When all the bills are in, Beaver will have poured something like $150,000 into the building. Pine paneling as much like the original as possible has replaced timbers deeply charred by last winter’s fire. Under the active craftsmanship of general contractor Charles R. Smital, who specializes in restorations and remodeling of this sort, Beaver’s law office now occupies the space where –according to neighborhood legend – Al Capone’s under-world demons once peered across Clark Street towards a bloody garage.

And on the ground floor has been built what Beaver calls “Chicago’s most exciting restaurant concept in many years”: THE CHICAGO PIZZA AND OVEN GRINDER COMPANY.”

Former Speakeasies

To keep with the theme I found former speakeasies that are still in business today as bars and restaurants. The Chicago bar project has offered a list of these bars here:

  • Burwood Tap (Wrightwood Neighbors)
  • Butch McGuire’s (Gold Coast)
  • Chipp Inn (Noble Square)
  • Club Lucky (Bucktown)
  • Continental (Humboldt Park)
  • Cork & Kerry (Beverly)
  • Durkin’s (West Lakeview)
  • Edgewater Lounge (Andersonville)
  • Emmit’s Pub (River West)
  • Exchequer Restaurant & Pub (Loop)
  • Glascott’s Groggery (Sheffield Neighbors)
  • Gold Star Bar (East Ukrainian Village)
  • Green Door Tavern (River North)
  • Green Mill (Uptown)
  • Halligan Bar (Lincoln Park)
  • Hangge Uppe (Gold Coast)
  • Hideout (Bucktown)
  • Inner Town Pub (East Ukrainian Village)
  • Jake’s Pub (East Lakeview)
  • Marge’s Still (Old Town Triangle)
  • O’Donovan’s (North Center)
  • Paramount Room (River West)
  • Rainbo Club (West Ukrainian Village)
  • Riverview Tavern (Roscoe Village)
  • Schaller’s Pump (Bridgeport)
  • Simon’s Tavern (Andersonville)
  • Twin Anchors (Old Town Triangle)

Read all about these former speakeasies in Historic Bars of Chicago written by Sean Parnell

Chicago is always a good idea. Here is another way of enjoying St. Valentine’s Day. If you are into true crime, history, or dark history, this is the tour for you. Happy planning!

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