Gangster Tour of Chicago

Unleash your inner Al Capone!
3 hours
from $127


Al Capone is long gone, but don't let that stop you from having a good time. Explore the most intriguing, mysterious and the most notorious places of Gangster Chicago in 3 hours.


  • 1. Little Italy
  • 2. 2222 South Wabash Avenue
  • 3. Holy Name Cathedral & North State Street
  • 4. Lincoln Park neighborhood
  • 5. Biograph Theatre
  • 6. Green Mill Bar


*The itinerary depends on how many stops you want to make during the tour, and may be revised.

*The tour can be modified to meet your preferences.


  • Exciting 3-hour Chicago Gangster Tour with your friendly local guide;
  • Follow the steps of famous Chicago gangsters;
  • See the places of bloody murders;
  • Immerse into the atmosphere of early 20th century;
  • Visit the Little Italy which used to be home to most gangsters;
  • Take a look at ex-headquarter of Al Capone and visit his favorite bar;
  • Listen to the exciting stories about Chicago gangsters;
  • Come to the place of terrifying St Valentine’s Day Massacre;
  • See the last place which was visited by John Dillinger;
  • Feel like a hero from a gangster movie.

Tour Itinerary:

Little Italy

Let’s immerse into the atmosphere of gangster Chicago in this legendary neighborhood. Little Italy, which is often called “Little Hell”, is the area which has given to Chicago the most famous and dangerous gangsters such as Johnny Torrio. Being an Italian ghetto since 1900s, Little Italy was a center of flourishing poverty, criminality and rule of mafia. Nowadays Little Italy is a quiet area with the best Italian restaurants in Chicago. But it’s so exciting to come here and feel the spirit of gangsters’ era.

2222 South Wabash Avenue

No doubt that you know one of the most famous gangsters in the world – Al Capone. His criminal way in Chicago started here, in the club “Four Deuces” which took its name from the address. In 1919 Al Capone worked here as a barker. Later, when he reached the top of mafia hierarchy, the “Four Deuces” became a center of criminal life of mafia housing a bar, a casino and a brothel. It was also famous by its cellar which was a place for numerous crimes.

Holy Name Cathedral & North State Street

Another big name of Chicago of 1920s is Dean O’Banion. Being very influential criminal authority and one of the founders of Chicago bootlegging empire, he had his headquarter based in Schofield’s flower store at 738 State Street. He chose this place because it was located just in front of the Holy Cathedral where O’Banion sang in the church choir and went for masses. O’Banion was killed in this headquarters that’s why this place is very significant. Another famous murder of his friend Earl Weiss took place near the Cathedral which still keeps the marks of bullets.

Lincoln Park neighborhood

In 1920s the area around Lincoln Park saw a great amount of bloody crimes. You will visit a place of one the most famous crimes here and will hear a story about St Valentine’s Day Massacre. In 1929 the struggle of two criminal gangs ended by the victory of Al Capone and 7 dead bodies of members of Irish Chicago gang. This event is extremely popular in modern culture and was mentioned in such famous films as Scarface, Some Like It Hot, The Untouchables.

Biograph Theatre

Founded in 1914, the Biograph Theatre belongs to the generation of the first movie houses in the USA and is considered to be one of the most famous Chicago Landmarks. But this theatre is mostly known as the place where legendary bank robber John Dillinger, who was declared #1 public enemy, was shot by FBI agents at 1934. Nowadays the Biograph is renovated but no changes can delete the unique spirit of this place. 

Green Mill Bar

How about ending our gangster tour with a drink in the bar? And not just in the bar, but in a very significant place. The Green Mile Bar was founded in 1907. It is famous by the fact that it was a favorite bar of Al Capone. Here you can even see the table where he and his gang were sitting. Sounds impressive, doesn’t it? Every evening the bar holds magnificent performances and jazz concerts. The atmosphere of this place is magic! 


  • * The itinerary is subject to change


Extra costs (per person):

Entrance fees


Activity Level: moderate
Maximum travelers: 5
Meet up & End location: lobby of your hotel
Start time: any time
Extra hours: If you are having a good time and want your Chicago Gangster tour last a little bit longer, you are welcome to do that. Please note: You will be charged 25 USD per an extra hour.
Tipping suggestions: If you feel like you had a good experience, your guide would appreciate a tip. It's not mandatory. It's your decision whether you want to give your guide a tip.

What you get:

  • + A friend in Chicago.
  • + Private & customized tour.
  • + An exciting pastime, not just boring history lessons.
  • + An authentic experience of local life.
  • + Flexibility during the tour: changes can be made at any time to suit individual preferences.
  • + Amazing deals for breakfast, lunch, and dinner in the very best cafes & restaurants. 
  • + A photo session amongst spectacular Chicago scenery that can be treasured for a lifetime.
  • + An expert advice on what to do, where to go, and how to make the most of your time.

*This Gangster tour in Chicago can be modified to meet your preferences.