Chicago Mob History Driving Tour

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Found inside Chicago’s historically Swedish neighborhood of Andersonville is the indispensable establishment of Simon’s Tavern. The tavern was named after the bar’s founder Simon Lundberg, a Swedish immigrant. After WWI, Lundberg operated a grocery store; but once Prohibition took effect, he secretly began selling whiskey with his coffee, likely acquiring the alcohol from Al Capone. Lundberg became so successful selling bootlegged whiskey that he afforded to purchase a new location for a second storefront which concealed the No Name Club speakeasy, which is the current location of Simon’s Tavern. After the end of Prohibition, Simon converted his storefront on Clark Street into a bar which continues to be a cornerstone establishment in the Andersonville neighborhood.

2. Green Mill Cocktail Lounge (Green Mill Gardens)

Chicago’s Green Mill Jazz Club, also known as the Green Mill Cocktail Lounge, is a historic music and entertainment venue in the city’s Uptown neighborhood. Dating back to 1907, the establishment was first named Pop Morse’s Roadhouse where it served patrons of the nearby Graceland and Saint Boniface cemeteries. Three years later, real estate developer Tom Chamales purchased the business and renamed it the Green Mill Gardens after Paris’ Moulin Rouge, subtly avoiding the implications of a red-light district by using the color green. The Green Mill continued to be a socially prominent Chicago dance hall and bar up until the Prohibition Act, during which time the dancing entertainment shifted to the popular Jazz movement that swept the country. During the era of Prohibition, the Green Mill famously served as a speakeasy as Al Capone ran illegal spirits through the Green Mill via underground tunnels before his arrest. During the rest of the 20th Century, the Green Mill’s condition slowly deteriorated from its once upscale past. Dave Jemilo purchased the venue in 1986 and brought it back to life. Today, the Green Mill once again hosts jazz concerts and weekly slam poetry events.

3. Biograph Theater (Victory Gardens Theater)

This historic theater opened in 1914. It is best-known as the theater that John Dillinger attended before being shot by Federal Agents. The building serves as reminder of the popularity of films and the rapid growth of theaters throughout the United States in the 1910s and 1920s.

4. John Barleycorn Speakeasy

This establishment in Lincoln Park is now a bar and grill, but at one time it operated as a speakeasy. The building is now occupied by John Barleycorn's and has stood in Lincoln Park since 1890. It began as a pub opened by an Irish immigrant moonlighting as a Chicago police officer. During Prohibition, the pub was boarded up on the exterior to appear vacant to the authorities. However there was a full-blown speakeasy operating on the inside. What is now the back room at John Barleycorn's was used to front a Chinese laundry, where bootleggers would roll in laundry carts loaded with booze under stacks of dirty clothes. The liquor was then transported to the basement where it was stored, and drinks were served by bringing bottles up in a small elevator. Costumers entered through the back laundry entrance, since the front of the building was boarded up.

5. St. Valentine's Day Massacre Site

The Saint Valentine's Day Massacre is the name given to the 1929 murder of seven mob associates of the North Side Irish gang led by Bugs Moran during the Prohibition Era. The massacre was the culmination of a power struggle as Al Capone took control of organized crime in Chicago. It remains the most infamous of all gangland slayings in America, and demonstrates both the cunning and savagery of Al Capone. By dressing his men as police officers, Capone was able to make his attack look like a normal police raid on bootleggers. Making it look as though they were only going to arrest the members of the rival gang (or seek a bribe) Capone's "police" officers opened fire after ordering the men to line up against the wall. After the massacre, the mob led by Al Capone and his successors controlled organized crime in Chicago

6. Holy Name Cathedral

Built in 1875, four years after the Great Chicago Fire, Holy Name Cathedral sits on Chicago's famous State Street amidst Chicago's towering skyscrapers. Holy Name operates as the seat for the Chicago Archdioceses, one of the largest and most influential Roman Catholic archdioceses in the United States. It also serves as a reminder of the influence of the church in Chicago and its neighborhoods, which increasingly grew Catholic as Germans, Irish, Polish and other immigrants from predominantly Catholic nations arrived in Chicago.

7. Green Door Tavern

One of Chicago’s oldest bars, the Green Door Tavern has witnessed much of the city’s history. After the Great Fire of 1871, James McCole constructed a two-story wooden frame building at the corner of Orleans and Huron Streets. Shortly after the building’s completion, the Chicago City Council passed an ordinance prohibited wooden framed structures so close to the Loop making the Green Door Tavern one of the oldest wooden buildings constructed after the fire. In 1921, Vito Giacomo took over the building and opened a restaurant called the Heron-Orleans. In the basement of the restaurant, Vito’s sons Jack and Nello ran one of the first speakeasies in the downtown which was mostly frequented by Chicago’s gangsters. Chicago’s Dean O’Banion, leader of the North Side Gang and rivals to Al Capone’s Chicago Outfit gang, provided the speakeasy’s illegal alcohol during the 1920s. During Prohibition, many speakeasies in Chicago featured a green door. Heron-Orleans’ green door was located on the building’s south side. As with most of Chicago’s former speakeasies and neighborhoods, the condition and reputation of the establishment fell considerably by the 1970s. In August 1985, George Parenti purchased the Green Door Tavern with the intent on renovating the building and returning it to its former glory. Since Parenti purchased the Green Door, the establishment has seen its return to popularity.

8. Cook County Jail

The correctional facility was built in the 1920s and has become the largest county jail in the United States. Over 100,000 detainees are admitted to the jail pending their trials each year. The facility covers more than eight city blocks and contains ten divisions, a health facility, two education departments, a commissary agency, and four onsite Sheriffs departments.

9. Mt. Carmel Catholic Cemetery

In the decade following the Great Fire of 1871, Chicago witnessed waves of new immigrants, most of which were Southern and Eastern European Catholics. Between 1885-1903, seven major catholic cemeteries were established within the Archdiocese of Chicago: Mt. Olivet, St. Mary, Holy Cross, Mt. Carmel, St. Casimir, Resurrection, and St. Joseph. Located in the Chicago suburb of Hillside, Mt. Carmel was consecrated in 1901 and quickly became associated with the city’s growing Italian population. Because its Italian connections, Mt. Carmel became the final resting place for many of Chicago’s famous gang members including Al Capone, his two brothers Frank and Ralph, the Genna Brothers, Dean O’Banion, “Machine Gun” Jack McGurn, Charles Nicoletti, and many others. Other famous burials include Jack Powell, Ken Silvestri, Julia Buccola Petta – known as the “Italian Bride,” and several members of the clergy.

This Tour is a Driving or Biking Tour.

Chicago Mob History Driving Tour

Created by Kalen Martin-Gross on December 5th 2018, 7:19:34 am.

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Description

Take a step back in time and view Chicago from the eyes of the city's famous Mob bosses such as Al Capone, Dean O'Banion, and John Dillinger. Beginning with two of Chicago's former speakeasies, Simon's Tavern and the Green Door Tavern, the tour continues to such sites as the St. Valentine's Day Massacre, the Green Mill Cocktail Lounge, and the Cook County Jail. The tour ends at the final resting place for many of these organized crime bosses, St. Carmel Catholic Cemetery.

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Chicago Mob History Driving Tour

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