100 Must-Read Books in and about Chicago

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Ashley Holstrom

Staff Writer

Ashley Holstrom helps make books at Sourcebooks. She lives near Chicago with her cat named after Hemingway and her bookshelves organized by color. Newsletter: Crooked Reads. Twitter: @alholstrom.

Ah, Chicago. The Windy City. The Second City. The Best City in the United States of America. The City with the Best Skyline, Certainly Better Than New York or Whatever. The City with the Best Pizza. The City of Hot Dogs, No Ketchup.

We’ve got 100 books in and about Chicago. We have fiction, nonfiction, and — bonus! — plays and poetry. Mystery, coming-of-age, adventure, history, sociology, race, class. We have it all. Oh, and a book about the 1985 Bears and another about Michael Jordan, because duh. Ever hear of a swell guy named Barack Obama? He’s from Chicago.


47th street black bayo ojikutu 47th Street Black by Bayo Ojikutu

An Abundance of Katherines by John Green

The Adventures of Augie March by Saul Bellow

American Gods by Neil Gaiman

Beautiful Bastard by Christina Lauren

Binding Arbitration by Elizabeth Marx

Black Iris by Leah Raeder

Bodies in Motion: Stories by Mary Anne Mohanraj

Building Stories by Chris Ware

Caramelo by Sandra Cisneros

chasing vermeer blue balliett

Chasing Vermeer by Blue Balliett

Chicago by Alaa Al Aswany

Chicago Noir: The Classics by Joe Meno

Chicago Stories: 40 Dramatic Fictions by Michael Czyzniejewski

Coffee Will Make You Black by April Sinclair

The Daughters by Adrienne Celt

Divergent by Veronica Roth

Divine Days by Leon Forrest

The Evolution of Bruno Littlemore by Benjamin Hale

A Fan’s Notes by Frederick Exley

For Fallon Soraya Naomi

For Fallon by Soraya Naomi

Free Burning by Bayo Ojikutu

The Fugue by Gint Aras

Generosity: An Enhancement by Richard Powers

The Good Girl by Mary Kubica

Good Kings Bad Kings by Susan Nussbaum

Hairstyles of the Damned by Joe Meno

The House on Mango Street by Sandra Cisneros

The Hundred-Year House by Rebecca Makkai

I Sailed with Magellan by Stuart Dybek

Indemnity Only Sara Paretsky

Indemnity Only by Sara Paretsky

The Jungle by Upton Sinclair

Kinda Sorta American Dream: Collected Stories by Steve Karas

The Lazarus Project by Aleksandar Hemon

Living With The Devil by Lori Hart, Cindy Hart

Malicious Masquerade by Alan Cupp

The Middlesteins by Jami Attenberg

Native Son by Richard Wright

Neanderthal Seeks Human by Penny Reid

O, Democracy! by Kathleen Rooney

The Old Neighborhood Bill Hillmann

The Old Neighborhood by Bill Hillmann

The Paris Wife by Paula McLain

Perfect Symmetry by Simone Elkeles

A Proper Pursuit by Lynn Austin

The Reason for Time by Mary Burns

Secrets of Sloane House by Shelley Gray

The Silent Wife by A.S.A. Harrison

Sister Carrie by Theodore Dreiser

So Big by Edna Ferber

Something Like Summer by Jay Bell

Sophomoric Philosophy Victor David Giron

Sophomoric Philosophy by Victor David Giron

Storm Front by Jim Butcher

Then We Came to the End by Joshua Ferris

The Time Traveler’s Wife by Audrey Niffenegger

Vibrizzio by Nicki Elson

White Collar Girl by Renee Rosen

Yummy: The Last Days of a Southside Shorty by G. Neri


American Project: The Rise and Fall of a Modern Ghetto by Sudhir Venkatesh

Black on the Block: The Politics of Race and Class in the City by Mary Pattillo

Blood Runs Green: The Murder That Transfixed Gilded Age Chicago by Gillian O’Brien


Bossypants by Tina Fey

Chicago: City on the Make by Nelson Algren

Chicago Flashbulbs: A Quarter Century of News, Politics, Sports, and Show Business by Cory Franklin

Chicago Haunts: Ghostly Lore of the Windy City by Ursula Bielski

City Life: Coming of Age in Chicago by John G. Linehan

City of Scoundrels: The 12 Days of Disaster That Gave Birth to Modern Chicago by Gary Krist

Cook County ICU: 30 Years of Unforgettable Patients and Odd Cases by Cory Franklin

Crook County: Racism and Injustice in America’s Largest Criminal Court by Nicole Gonzalez Van Cleve

The Defender: How the Legendary Black Newspaper Changed America by Ethan Michaeli

The Devil in the White City: Murder, Magic, and Madness at the Fair that Changed America by Erik Larson

Dreams from My Father by Barack Obama

Dreams from My Father: A Story of Race and Inheritance by Barack Obama

Family Properties: Race, Real Estate, and the Exploitation of Black Urban America by Beryl Satter

Gang Leader for a Day: A Rogue Sociologist Takes to the Streets by Sudhir Venkatesh

Gangland Chicago: Criminality and Lawlessness in the Windy City by Richard C Lindberg

The Girls of Murder City: Fame, Lust, and the Beautiful Killers who Inspired Chicago by Douglas Perry

Gold Coast Madam: The Secret Life of Rose Laws by Rose Laws

High Rise Stories: Voices from Chicago Public Housing by Audrey Petty

Just Add Water: Making the City of Chicago by Renee Kreczmer

Lost Chicago by John Paulett

Meaty: Essays by Samantha Irby

Michael Jordan by Roland Lazenby

Michael Jordan: The Life by Roland Lazenby

Monsters: The 1985 Chicago Bears and the Wild Heart of Football by Rich Cohen

My Kind of Sound: The Secret History of Chicago Music by Steve Krakow

Negroland by Margo Jefferson

Off the Books: The Underground Economy of the Urban Poor by Sudhir Venkatesh

Relish: My Life in the Kitchen by Lucy Knisley

Sin in the Second City: Madams, Ministers, Playboys, and the Battle for America’s Soul by Karen Abbott

Slaughterhouse: Chicago’s Union Stock Yard and the World It Made by Dominic A. Pacyga

The South Side: A Portrait of Chicago and American Segregation by Natalie Y. Moore

South Side Girls: Growing Up in the Great Migration by Marcia Chatelain

The Story of Jane by Laura Kaplan

The Story of Jane: The Legendary Underground Feminist Abortion Service by Laura Kaplan

Strike for America: Chicago Teachers Against Austerity by Micah Uetricht

Sweetness: The Enigmatic Life of Walter Payton by Jeff Pearlman

There are No Children Here: The Story of Two Boys Growing Up in the Other America by Alex Kotlowitz

Who Do You Serve, Who Do You Protect? Police Violence and Resistance in the United States by Maya Schenwar

The Working Man’s Reward: Chicago’s Early Suburbs and the Roots of American Sprawl by Elaine Lewinnek

Yes Please by Amy Poehler


Chicago Poems by Carl Sandburg

Maud Martha by Gwendolyn Brooks

A Raisin in the Sun by Lorraine Hansberry