Is this walking tour Chicago mob history themed?

Yes, this self-guided route focuses specifically on the Prohibition era. You will see sites related to Al Capone, the St. Valentine's Day Massacre, and the death of John Dillinger.

Can I see where the St. Valentine's Day Massacre happened?

The actual garage at 2122 N. Clark St. was demolished in 1967. However, you can stand across the street at the Chicago Pizza and Oven Grinder Company, which used to be a lookout for the killers, and view the fenced-in lot where the massacre occurred.

Is it safe to walk through Lincoln Park and Uptown?

Lincoln Park is one of Chicago's safest neighborhoods. Uptown, where the Green Mill is located, is a busy entertainment district that is generally safe during the evening, though visitors should stay aware of their surroundings as they would in any urban area.

What is the best time of day for this audio walk?

Late afternoon is ideal. This allows you to see the architectural details and bullet holes in daylight, while finishing at the Green Mill just as the jazz music and evening atmosphere begin.

Are there any tickets required for this route?

No tickets are required to view the exteriors of these landmarks. If you wish to enter Harry Caray's or the Green Mill, you may want to check their specific schedules or make a reservation for a meal.

Is the route accessible for strollers or wheelchairs?

The sidewalks are standard city concrete and generally accessible. Because the stops are spread across several miles, those using wheelchairs will likely need to use accessible transit like the 'L' trains or a ramp-equipped vehicle between neighborhood stops.

Can I see Al Capone's actual house on this walk?

No, Al Capone's primary residence was on the South Side of Chicago. This walk focuses on his business operations and 'work' sites in the River North, Lincoln Park, and Uptown areas.

Zigway - The Guide Follows You

About This Tour

Step into the shadows of the Roaring Twenties on a journey through Chicago’s most notorious era. This self-guided walk explores the bloody rivalries and secret hideouts of the Prohibition era, tracing the footsteps of icons like Al Capone, John Dillinger, and the North Side Gang. As you navigate the streets from River North to Uptown, you will uncover the stories of the bootleggers and enforcers who turned the Windy City into a battlefield for control of the underground liquor trade. This walking route Chicago enthusiasts love offers a deep dive into the architecture and alleyways where history was written in lead and jazz. Your journey begins at the former home of one of Capone’s top enforcers, where secret vaults lay hidden for decades. From there, you will visit a cathedral that still bears the physical scars of a gangland assassination, a testament to the era's lawlessness. As you move north into Lincoln Park, the route brings you to the site of the most infamous crime in American history: the St. Valentine's Day Massacre. You will also stand on the very pavement where 'Public Enemy Number One' met his end outside a local cinema. Finally, the trail concludes at a legendary jazz club that has remained virtually unchanged since the days when 'Scarface' himself sat in the corner booth. This audio walk provides the historical context and chilling details that bring the era of tommy guns and speakeasies back to life, all at your own pace.

Highlights

Discover the hidden vault of Frank Nitti at Harry Caray's

See the bullet-scarred cornerstone of Holy Name Cathedral

Stand across from the site of the St. Valentine's Day Massacre

Trace the final steps of John Dillinger outside the Biograph Theatre

Visit Al Capone’s favorite booth at the historic Green Mill

Tour Stops (5)

Harry Caray's Italian Steakhouse

Start your journey at a building that was once the residence of Frank 'The Enforcer' Nitti, Al Capone’s top lieutenant. While it is now a famous steakhouse, the structure’s dark past was revealed during renovations in the 1990s. Workers discovered a hidden vault and a series of secret rooms used by Nitti to coordinate the Outfit's operations. The building even featured a sophisticated 'pigeon hole' telephone system to evade police wiretaps. As you stand here, imagine the smoke-filled rooms where Nitti managed the enforcement of Capone’s empire before his own tragic end near the railroad tracks.

Holy Name Cathedral

This stunning Gothic Revival cathedral was the site of one of the most brazen hits in Chicago history. In 1926, Hymie Weiss, leader of the North Side Gang and a bitter rival of Al Capone, was ambushed by gunmen hidden in a nearby rooming house. As Weiss and his associates walked past the cathedral, they were met with a hail of bullets. If you look closely at the cornerstone near the entrance, you can still see the damage left by a stray bullet. This site symbolizes the era when even the steps of a sanctuary weren't safe from the city's violent gang wars.

Chicago Pizza and Oven Grinder Company

You are now standing in the heart of Lincoln Park, directly across from the site of the St. Valentine's Day Massacre. On February 14, 1929, seven members of the North Side Gang were lined up against a wall in a garage and executed by gunmen dressed as police officers. While the garage was demolished in 1967, the building you see now—the Chicago Pizza and Oven Grinder Company—served as a lookout for the killers. The eerie atmosphere of this quiet street belies the fact that it was once the scene of the most famous mob hit in history, an event that eventually led to Capone's downfall.

Victory Gardens Theater

Formerly known as the Biograph Theatre, this is where the era of the 'celebrity outlaw' came to a violent end. In July 1934, John Dillinger, known as 'Public Enemy Number One,' was betrayed by the 'Lady in Red' and ambushed by FBI agents as he exited the theater. Dillinger attempted to flee into the adjacent alley but was shot and killed. The theater’s facade remains largely unchanged, allowing you to visualize the chaos of that summer night. Dillinger's death marked the beginning of the end for the lawless Depression-era bandits who had captured the public's imagination.

The Green Mill

This legendary jazz club is one of the oldest in the country and was a primary hang-out for Al Capone. 'Scarface' had a preferred booth here, positioned specifically to provide a clear view of both the front and back entrances. Beneath the floorboards, a network of tunnels—some of which still exist—allowed for the discrete delivery of illicit booze and quick escapes during raids. Today, the Green Mill maintains its authentic 1920s atmosphere, with the same neon sign and Art Deco interior that Capone and his associates enjoyed while listening to the greats of Chicago jazz.

Frequently Asked Questions

The full walk takes approximately 90 to 120 minutes. This includes time to stop at each landmark and covers several miles, though most people use the Red Line train to jump between the neighborhood clusters of River North, Lincoln Park, and Uptown.