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The Best Books About Chicago

Posted on September 4, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

A Little Free Library in Pilsen in 2023

A Little Free Library in Pilsen in 2023. (Trent Sprague / Chicago Tribune / Getty)

While you’re perusing new finds at the Printer’s Row Lit Fest this weekend and South Side Lit Fest next weekend, consider adding these Chicago books to your fall reading list.

On Chicago History: ‘The South Side

Journalist Natalie Moore’s book should be required reading for Chicagoans to understand the history of segregation in the city — and why it persists.

  • 🥈 “Boss” is a deep dive into Mayor Richard J. Daley and the political machine he ran for decades. Pro-tip: Mike Royko’s book is especially handy for Chicago History Fair projects.
  • 🥉 “We Are the Culture: Black Chicago’s Influence on Everything” by Arionne Nettles dives into everything from “Soul Train” to the Johnson Publishing Company to Chance the Rapper.

For Transplants: ‘The Chicago Neighborhood Guidebook

You could spend a lifetime in the city and still have so much to explore: This anthology gives you a sense of Chicago’s 200ish neighborhoods through essays, photos, and more.

In the wake of her sister’s death, Julia navigates grief, identity, and family in this popular young adult book. Erika L. Sanchez’s story has been adapted into a play and will soon be a movie.

  • 🥈 “The Great Believers” by Rebecca Makkai is another tearjerker following the devastating effects of the AIDS crisis in Chicago in the ‘80s.

For Your Inner Child: ‘Ironheart

This Marvel comic book follows Riri Williams, the South Side superhero who re-engineered Iron Man’s suit to save the day. Chicago poet Eve L. Ewing has range for days — she’s also written about the 1919 race riots, CPS, and more.

City Cast

Eve Ewing Takes on Everything From Chicago Race Riots to Marvel Comics

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A photo from “Chicago Protests: A Joyful Revolution.”

A photo from “Chicago Protests: A Joyful Revolution.” (Courtesy of Vashon Jordan Jr.)

Photographer Vashon Jordan Jr. captured 2020 protests — and other moments of joy during an otherwise tumultuous summer.

City Cast

Chicago Photographer Captures ‘Joyful Revolution’

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Journalist Dawn Turner chronicles the different paths life took her, her sister, and their best friend after growing up inseparable in the historic South Side neighborhood in the 1970s.

Chicago is known for classics like deep-dish and Italian beef, but don’t sleep on mild sauce or the jibarito. Chicago journalists Monica Eng and David Hammond share recipes and recommendations for local dishes.

City Cast

Have You Tried These ‘Hometown Bites’ From Chi?

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After you get all your books, join a book club!

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