15 Chicago Gangster Books to Add to Your List

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. 

Books About Chicago Gangsters

1. Al Capone: His Life, Legacy, and Legend

Al Capone: His Life, Legacy, and Legend

Written by: Deirdre Bair

Published: October 25th, 2016

Pages: 432  

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.

2. Capone: The Man and the Era

Capone: The Man and the Era

Written by: Laurence Bergreen

Published: August 5th, 1996

Pages: 704

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.

3. The Untouchables

The Untouchables

Written by: Eliot Ness, Oscar Fraley

Published: 1957

Pages: 256

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.

4. Capone: The Life and World of Al Capone

Capone: The Life and World of Al Capone

Written by: John Kobler

Published: 1971

Pages:  409

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.

5. The St. Valentine's Day Massacre: The Untold Story of the Gangland Bloodbath That Brought Down Al Capone

The St. Valentine's Day Massacre

Written by: William J. Helmer, Arthur J. Bilek

Published: October 1st, 2003

Pages:  305

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.

6. Family Secrets: The Case That Crippled the Chicago Mob

Family Secrets

Written by: Jeff Coen

Published: April 1st, 2009

Pages:  400

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.

7. Family Affair: Greed, Treachery, and Betrayal in the Chicago Mafia

Family Affair

Written by: Sam Giancana, Scott Burnstein

Published: March 2nd, 2010

Pages: 294

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.

8. American Mafia: Chicago: True Stories of Families Who Made Windy City History

American Mafia: Chicago

Written by: William Griffith

Published: October 1st, 2013

Pages: 232

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.

9. The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hit Man

The Tangled Web

Written by: Michael J. Cain

Published: April 17th, 2007

Pages: 240

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.

10. Bugs Moran: The Notorious Life and Legacy of the Chicago Gangster Who Became Al Capone’s Biggest Rival

Bugs Moran

Written by: Charles River Editors

Published: February 5th, 2019

Pages: 108

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.

11. Umbrella Mike: The True Story of the Chicago Gangster Behind the Indy 500

Umbrella Mike

Written by: Brock Yates

Published: June 21st, 2006

Pages: 250

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.

12. Al Capone and the 1933 World’s Fair: The End of the Gangster Era in Chicago

Al Capone and the 1933 World’s Fair

Written by: William Hazelgrove

Published: September 15th, 2017

Pages: 250

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.

13. Black Gangsters of Chicago

Black Gangsters of Chicago

Written by: Ron Chepesiuk

Published: August 29th, 2007

Pages: 334

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.

14. Uncle Al Capone - The Untold Story from Inside His Family

Uncle Al Capone

Written by: Deirdre Marie Capone

Published: October 27th, 2010

Pages:  232

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.

15. Scarface and the Untouchable: Al Capone, Eliot Ness, and the Battle for Chicago

Scarface and the Untouchable

Written by:  Max Allan Collins, A. Brad Schwartz

Published: August 14th, 2018

Pages: 736

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.