One of the most populous cities in the United States, Chicago is a place full of fascinating sights that had to go through a lot of changes to become the metropolis it is today. Whether you're interested in diving deep into the history of The Windy City, or want to know how to navigate modern-day Chi-Town, you might want to read up on the subject. Let's take a look at the 10 best books about Chicago, which cover everything from fictionalized accounts of the city to detailed travel guides.

The 10 Best Books About Chicago

  1. Chicago Then and Now: Photos of the city
  2. 111 Places in Chicago That You Must Not Miss: An insider's guide
  3. Chicago: A Novel: A young man and his dog experience Chicago
  4. Chicago Flashback: The people and events that shaped history
  5. DK Eyewitness Travel Guide: Chicago: Suggestions for travelers
  6. A People's History of Chicago: Poems about a Chicagoan's life
  7. Chicago: America's Railroad Capital: An illustrated history
  8. Chicago: A Biography: Details about the area's past
  9. Chicago on the Make: Power and inequality in a modern city
  10. Not For Tourists Guide to Chicago: A map-based guide

Famous Women in Chicago's History

Why Learn About Chicago?

Tourists traveling anywhere from New York to Paris to (of course) Chicago can benefit from reading about what attractions their destination has to offer. Even long-time locals might be surprised to find that a fun attraction or amazing restaurant has been sitting under their noses for years. And everyone can benefit from learning more about history. Knowing about a city's past can make residents feel more connected to their roots and let tourists appreciate the sights they're seeing on a different level.

More Interesting Things to Read About

4K Footage of Chicago From Above

More Information

The City of Chicago, often referred to as the "Windy City," is the third largest metropolitan area in the United States. After the "Great Chicago Fire" in 1871, the municipality saw the opportunity to reinvent itself, and went on to become a global center for commerce and culture. With over 50 million visitors annually, Chicago is considered to be one of the most-visited cities in the country.

It boasts tourist attractions which include "Millennium Park," "Willis Tower Skydeck," "Art Institute of Chicago," and "Navy Pier," among others. So whether you are planning a trip to the Windy City anytime soon, or just want to learn more about Illinois's most populous community, our list of the ten best books about Chicago can serve as your guide.

Starting off at #1 is "Chicago Then and Now." This book tells the story of the city's heritage by comparing Chicago's old and modern photographs. Written by Kathleen Maguire, this volume includes information that explains the municipal's history. It also contains a detailed map which lists the book's featured sites such as "Grant Park," "North Michigan Avenue," and more. This book is for anyone who is fond of the city's historical background and for the people who grew up in Chicago.

At #2 is the "111 Places in Chicago That You Must Not Miss." This book features unusual places in Chicago which are not found in traditional travel materials. It was written by Amy Bizzarri, a family travel expert for Chicago's Board of Tourism. According to her, the book serves as a guide for those who want to discover unpopular yet interesting spots in Chicago. It is also considered a "bucket list" for Chicagoan adventurers and long-term tourists.

Coming in at #3 is "Chicago: A Novel." The narrative begins with a young man who takes his first job as a journalist and rents an apartment in Chicago. Through the author's evocative writing, the readers will find themselves transported in the man's perspective as he encounters daily life in the Windy City. Written by the late Brian Doyle, this novel triggers one's imagination as he vividly describes every detail that brings Chicago to life. This book is for those who not only want to read about the city, but also experience its community in the 70s.

What we have at #4 is "Chicago Flashback: The People and Events That Shaped a City's History." Written by the editors of the "Chicago Tribune" newspaper, this book presents the city's archival photos together with its corresponding stories. The volume is broken into chapters such as sports, individuals, and events, among others.

According to the authors, this book helps people resonate what it is like to be a Chicagoan at a certain period. They stated that they had been getting much positive feedback from the people reading their "Flashback" feature in the newspaper. Hence, they decided to compile those stories and turn it into a book.

At #5 is the "DK Eyewitness Travel Guide: Chicago." This book is for those who want to maximize their stay in Chicago. With detailed itineraries and destination highlights, this volume serves as a guide in discovering the Windy City. It also includes area maps, floor plans and 3-D drawings of tourist attractions, insights into the city's history, hotel and restaurant listings, places to shop, activities to try, and more.

Coming in at #6 is "A People's History of Chicago." Written by poet Kevin Coval, this book tells the stories of the marginalized communities in Chicago. The author narrates the unknown face of the municipality's history through his collection of poems. It recounts the people who struggled, endured, and fought for justice to make the city a better place. This book is recommended for those who want to learn how patriotism molded Chicago.

At #7 on our list is "Chicago: America's Railroad Capital: The Illustrated History, 1836 to Today." Chicago is known to be the most significant transportation hub for the nation, linking east to west and north to south of the United States. This book is for anyone who is fascinated with the history of Chicago's railroads and its operational process. Written by railway historian Brian Solomon, the volume details the history and infrastructure of the city's train line. It also includes archival black-and-white photos, as well as modern-day pictures of the railway.

What we have at #8 is "Chicago: A Biography." Aside from the nickname "Windy City," Chicago has been dubbed many names such as "City of the Big Shoulders," "The Second City," and more. However, this book presents that regardless of all those labels, the real Chicago is found within the hearts of its citizens. Author Dominic Pacyga narrates the city's growth, explains its fundamentals, and analyses how Chicago came to be. This book is not only for native Chicagoans, but also for the people who plan to do business in the community.

At #9 is "Chicago on the Make: Power and Inequality in a Modern City." Written by Andrew Diamond, the book tells the story of the city's evolution from the early 20th century up to 2016. It traces the development of Chicago's government, culture, and economy. It also details the society's origins and the politics of racism. This book is for those who are searching for in-depth information about the history of Chicago's progress.

Finally, at #10 is the "Not for Tourist Guide to Chicago 2018." Aside from Chicago's must-see attractions, this map-based book features the essentials within the community. It provides information such as public transportation, supermarkets, pharmacies, restaurants, and more. The book divides the city into sixty mapped neighborhoods, and plots the services within the area.

Each book provides a different perspective of Chicago. They will equip you with details that will suit your need, style, or interest. According to one of the book's reviewers, reading about Chicago not only helps him appreciate the city's development, but also be aware of its historical character.

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