Discover 15 of the best Chicago gangster books. The Windy City has been well known for its crime throughout history. Here you will find exciting reads about these mobsters and organized crime.
You will also find quite a few Al Capone books. This mob boss is almost synonymous with Chicago in the 1920s and 1930s when the mafia was significant in the Windy City.
Written by: Deirdre Bair
Published: October 25th, 2016
Al Capone was a criminal mastermind who ran an empire of crime that stretched from coast to coast in his lifetime. He ruled with impunity until the day he woke up in a jail cell and found himself on trial for tax evasion. From his humble beginnings as a tough kid from Brooklyn to the heights of power in Chicago, Capone's story is one of ruthless ambition and unmatched ruthlessness.
In this biography about Al Capone, author Deirdre Bair delves deep into the life of America's most notorious gangster to paint a complete portrait - not just of "Scarface" but also Al Capone, the family man.
Written by: Laurence Bergreen
Published: August 5th, 1996
Capone: The Man and the Era is another excellent book about the rise and fall of Al Capone. This one focused much of its attention on Prohibition and how he rose to power on the seedy Chicago streets.
Laurence Bergreen digs deep into his illicit liquor trade and how it turned the streets of the Windy City into a battleground.
It also covers his role as a doting father and son and his role as a local celebrity.
Written by: Eliot Ness, Oscar Fraley
This autobiography by Eliot Ness tells of his role in taking down the mob in Chicago in the 1920s and 1930s. Ness worked for the Bureau of Prohibition as a federal agent and had a front-row to the criminal scene throughout Chicago.
Written back in 1957, this book became even more popular when it was turned into a television series and eventually a movie in 1987.
Written by: John Kobler
Capone: The Life and World of Al Capone is another nonfiction book that takes you back in time to when Al Capone ruled Chicago. It covers his violent childhood in Brooklyn, his move to Chicago, and his reign as the boss of the Chicago mob during Prohibition.
After his arrest, Capone spent time in some prisons where he set his own rules. He then moved to Alcatraz, where things changed dramatically for him.
It's one of the highest-rated Chicago gangster books on our list.
Written by: William J. Helmer, Arthur J. Bilek
Published: October 1st, 2003
If you are familiar with Chicago during Prohibition, then I'm sure you've heard about the St. Valentine's Day Massacre. However, do you know what happened?
This book takes you back to February 14, 1929, in Chicago, when several mobsters dressed as cops, killed several other mobsters in cold blood. Immediately, everyone pointed the finger at Al Capone (even though he wasn't anywhere near Chicago at the time).
This event led to Capone’s downfall.
This book is the first to focus specifically on this important event in Chicago’s history and how it became a turning point for Al Capone and his gang.
Written by: Jeff Coen
Published: April 1st, 2009
Moving forward a few years to the 60s, 70s, and 80s, this book takes you to a time when organized crime still gripped the city of Chicago. It walks you through what was happening at the time and those responsible.
Finally, in 1998, Frank Calabrese Jr., part of the mob, agreed to wear a wire. The information he gathered helped bring this Chicago Mob to its knees.
The story offers a look into the lives of those involved and what happened during their trials.
Written by: Sam Giancana, Scott Burnstein
Published: March 2nd, 2010
This is another look at the more recent gangsters in Chicago's history. This book offers the story of Nicholas "Nicky Breeze" Calabrese, who turned states witness.
He helped take down some of the most recent mobsters in the history of the Windy City.
Written by: William Griffith
Published: October 1st, 2013
This is a great look back in the history of Chicago gangsters. You’ll learn all about early mobster stories and the places where those events took place.
It's a complete look at when the city was overrun by gangs, their interwoven relationships, and how it changed Chicago forever.
Written by: Michael J. Cain
Published: April 17th, 2007
Richard Cain is known as one of the most corrupt cops in the history of the Chicago police force. In the mid-1950s, he worked as an officer for the Chicago Police Department.
He played a double role as a close associate of Sam Giancana, who was the boss of the Chicago Outfit from 1957 to 1966.
Written by his brother, The Tangled Web takes you back to the life and death of Cain, including how he helped the mafia with a variety of jobs.
Written by: Charles River Editors
Published: February 5th, 2019
We've all heard about Al Capone, but have you read much about Bugs Moran's rival? This short book offers a look at the other side of the criminal streets of Chicago in the 1920s and 1930s.
You'll learn about how he became an important figure in the mafia, what his life was like as a gangster and more about the St. Valentine's Day Massacre.
Written by: Brock Yates
Published: June 21st, 2006
Another infamous gangster in Chicago was Michael Joseph Boyle, also known as Umbrella Mike. In addition to being the leader of one of the most powerful unions, Umbrella Mike was also part of the Chicago Outfit.
He also loved cars, and his dream was to win the Indianapolis 500.
This book takes you through who he was a mobster, a union leader, and his quest to win the ultimate car race.
Written by: William Hazelgrove
Published: September 15th, 2017
This book focused on critical events leading up to the 1933 World Fair in Chicago. It was a time when "The Secret Six" were in an all-out effort to bring down Al Capone, the Great Depression was beginning, and Prohibition was ending.
It takes you through everything Chicago had to do to pull off this international, historical event.
Written by: Ron Chepesiuk
Published: August 29th, 2007
Black Gangsters of Chicago takes a look at another group of powerful mobsters throughout history. It takes you into the lives of John Mushmouth Johnson, Jeff Fort, and Larry Hoover.
You’ll read never before uncovered facts that prove that these African American gangsters were just as powerful as their white counterparts, even though they didn’t get the press or the fame at the time.
Written by: Deirdre Marie Capone
Published: October 27th, 2010
If you are still craving to read more books about Al Capone, this is another excellent read.
One of the few insiders looks at the mobster known as Scarface. Dierdre Marie Capone spent several years inside the Capone household and showed what happened at home.
You'll meet more of his family and secrets that no one else in the family has ever published.
Written by: Max Allan Collins, A. Brad Schwartz
Published: August 14th, 2018
This is another great read about the relationship between Al Capone, a gangster, and Eliot Ness, a law enforcement officer. You'll learn all about some of the most critical criminal events and how these two battled for control over Chicago.
It’s a great look at both sides of what was happening in the Windy City in the 1920s and 1930s.