The 13 Best Documentaries About Chicago

Aug 6, 2023 | Best Of, Culture, History

When it comes to the great city of Chicago, there is so much to explore and discover. From its iconic landmarks, vibrant culture, and rich history – the Windy City has plenty of stories that are begging to be told. But what better way to experience all these stories than through documentaries? Whether you’re a tourist or a local – these 13 best documentaries about Chicago will give you an in-depth look into the lives and lifestyles of its people as well as some truly remarkable moments from its past. So grab your popcorn and get ready for an immersive journey into one of America’s most beloved cities!


1. Chicago at the Crossroad

Chicago is known for its rich history, vibrant culture and diverse communities. But what happens when these elements collide? This documentary takes a deep dive into the city’s struggles with mass displacement policies and segregation that have caused violence in the aftermath. Follow along as Chicago is thrown at the crossroad of chaos, inequality and injustice to get a better understanding of this complex issue.


2. Chicago, IL Most Dangerous Neighborhoods : Gangs & Crime

Chicago is a city with a long and storied history. But it’s also home to some of the most dangerous neighborhoods in the United States, due to gang activity and high crime rates. In this documentary, we take an in-depth look at Chicago’s streets – exploring not only why they are so dangerous but also how its citizens are fighting back against the violence that has plagued their city for decades. Get an up-close look at one of America’s biggest cities and uncover what makes it such a hotbed for crime.


3. Chicago USA. 3rd Largest City in the US

Chicago is an amazing city, and it’s the 3rd largest in the US! It has a lot to offer from history and culture to cuisine. This documentary takes you on a journey through this incredible city, showing you its highlights as well as some hidden gems. You’ll get a great insight into what makes Chicago so unique and why it’s one of the most popular cities in America. So join us for an amazing tour of Chicago USA!


4. Gangs and guns: stopping Chicago’s revenge killings

Chicago is known for its vibrant culture and friendly people, but the city has been plagued by an increase in gang violence. In this documentary, Unreported World takes us to Chicago’s inner-city neighborhoods to meet the rival gangs and individuals working hard to stop what has become a pattern of revenge killings. Hear from those living in trauma as they share stories of how they are trying to end these tragic murders and protect their communities.


5. Life & Death on the Chicago Streets

Chicago has been a city of tragedy recently, with an unprecedented rate of gun violence and police brutality impacting its people. In this documentary, Reggie Yates examines the life and death on the Chicago streets to investigate who is responsible for the 468 murders that occurred in 2015. He looks deep into the plight of many young African-American men affected by these crimes and how it continues to devastate their lives. Join us as we explore this heartbreaking tale in President Obama’s adopted hometown.


6. Homeless Teenagers Surviving Chicago Winter

Following the lives of three homeless teenagers, this documentary explores how they bravely face the struggles of Chicago’s winter and pressures of high school while living on their own. It shows inspiring stories as these young people create new definitions for home despite their traumas and abandonment. With determination and resilience, will they be able to build a brighter future?


7. The Entire History of Chicago In 17 Minutes

Chicago is an incredible city with a fascinating history. From its humble beginnings as a small trading post to the bustling metropolis it is today, Chicago has been home to some of America’s most influential people and events. This video dives into the city’s rich past, highlighting important moments in its history that have shaped what it is today — all in just 17 minutes! Watch this video and explore how Chicago has transformed over time and how those changes have impacted residents.


8. Chicago’s gang war: a crisis like no other

Chicago is one of the most sophisticated cities in the world, but it’s south side is facing a crisis like no other. Every two hours someone is shot and every 14 hours someone is murdered due to gang rivalry that has become so brutal its out of control. This documentary will explore this urban warfare and how it’s tearing apart the people living there. Get an inside look at what goes on in Chicago and learn more about the city’s ongoing struggle with violence.


9. Meet Gang Members From Chicago’s West Side

Chicago has been experiencing a wave of gun violence in recent years and President Trump took notice. To help find a solution, 12 days after his inauguration, the president was contacted by Pastor Darrell Scott who said he had heard from “top gang thugs” with an offer to help. In this documentary we explore the story behind these mysterious claims and investigate if it is possible for gangs in Chicago’s West Side to be part of the solution.


10. History of the Most Violent Roadways in Chicago

Chicago has a dark and violent history, particularly in the south and west sides of the city. This two-hour documentary examines 4 of Chicago’s most dangerous roadways that have been home to gangs, violence, and policy failures for over a century. It’s an eye-opening look at how these neighborhoods have been affected by their surroundings – from parks to gangs – and will leave you with a better understanding of this troubled region.


11. The Union Stockyards — A Chicago Stories

Chicago is a city with an amazing history and the Union Stockyards have played an important role in it. This documentary will take you back to the end of the 19th century, when Chicago completely changed how Americans eat. You’ll explore the sights, sounds, and smells of this revolutionary place as well as Packingtown – a complex of meat factories next to it. Discover the story behind why Chicago became known as “The Meatpacking Capital” and learn more about its fascinating past!


12. The Gang History Of Chicago

Explore the turbulent history of Chicago’s gang culture. From its humble beginnings with Prohibition-era mobsters, to modern day street gangs, this documentary dives deep into 100 years of the Windy City’s tumultuous past. Follow along as we uncover stories from those who experienced it firsthand and explore how far Chicago has come since then. This is an essential look at a part of American history that too often goes untold.


13. Remembering Old Chicago History

Chicago is a city with an incredible history. From the mobsters and gangsters of the south side to the times before crime was so prevalent, learn more about Old Chicago History in this documentary. This video will take you back in time and explore important figures, moments and events that shaped Chicago into what it is today. Learn about guns, violence, crime and other aspects of life during those times for a deeper understanding of our beloved city’s past!

Read On – Our Latest Top Documentaries Lists

David B