The 40 Books Every Chicagoan Must Read

A Chicago bibliography for the discerning reader

By Michael Nolledo

The 40 Books Every Chicagoan Must Read
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27 January 2016

Reading, n.: The act of reading; perusal; recitation.

Anyone still doing that?

A question that needs not an answer, but rather a firm push in the write direction. 

Thusly, we present the 40 Books Every Chicagoan Must Read, an unranked, genre-neutral, incomplete-but-when-is-anything-ever-really-complete celebration of the most enchanting voices that have made literal our fair city’s history.

Why these forty? Aside from those who could not be absent — Algren, Terkel, Sandburg, Sinclair, Brooks — our choices are wholly democratic.

These are by no means the best books written in, about or in spite of Chicago.

We just love them. And have learned from them. And hence desired to write about them. 

Before you dig in — a few words, about the written word, from a famous Oak Parker named Ernest Hemingway:

“All good books are alike in that they are truer than if they had really happened and after you are finished reading one you will feel that all that happened to you and afterwards it all belongs to you: the good and the bad, the ecstasy, the remorse and sorrow, the people and the places and how the weather was. If you can get so that you can give that to people, then you are a writer.”

The books below? True to Chicago. Happy reading.



01 Division Street by Studs Terkel 
A patchwork collection of self-portraits pertaining to Chicago life, culled from 70 interviews conducted and edited by the city’s greatest listener. Terkel teaching Chicagoans about Chicagoans.

02 Chicago: City on the Make by Nelson Algren 
The ignoble ode to Chicago that develops like a photographic negative of the city. Basically, an urban creed that should be issued to all incoming residents immediately upon arrival.

03 You Were Never In Chicago by Neil Steinberg 
A contemporary newspaper man’s celebration of Chicago. The longtime Sun-Times columnist is a skilled observer, and his little personal quips on city life resonate.

04 The Third Coast: When Chicago Built the American Dream by Thomas Dyja 
The anti-”Second City” book from a Northwest Side native that covers a pantheon of Chicagoans and their contributions to the world. Additional listening: Dyja on the Freakonomics radio podcast.

05 The Man With the Golden Arm by Nelson Algren
Algren's Chicago is home for the strange, downtrodden and ruined. Skip the film for the book, you pay a much better price for admission.

06 The Studs Longinan Triology by James T. Farrell
Fun fact: Studs Terkel was nicknamed after Studs Longinan — the tough guy protagonist in Farrell’s three-part story of a South Side Irish kid who dreams big and falls hard. Written and set between 1929 and 1935.

07 The Adventures of Augie March by Saul Bellow
“I am an American, Chicago born” begins this 1954 classic from hometown Nobel Prize-winning laureate. Augie March’s Chicago: Humboldt Park during the Great Depression.

08 I Sailed With Magellan by Stuart Dybek
A beautiful collection of stark interlocking short stories set in Little Village during the 1950s and ‘60s, where the concept of people and place are seemingly interchangeable.

09 Crossing California by Adam Langer
Crossing California as in California Avenue. A humorous lens of growing up Jewish in the very Jewish enclave of West Rogers Park. Lots of family in this one.

10 Trumbull Park by Frank London Brown
A fictional tale of black man who moves his family out of the South Side ghettos to Trumball Park, a white public housing project, and the racial tensions that ensue. An underrated gem.

11 There Are No Children Here by Alex Kotlowitz
A dark, biographical account of two brothers raised in the Henry Horner public housing development in the 1980s.

12 Native Son by Richard Wright
Wright’s Noir masterpiece. A gripping look into the psychology of systemic racism in America, a problem that may or may not sound familiar today. 

13 Letting Go by Philip Roth
It might be a brick to carry around (nearly 700 pages), but it’s an interesting study on domestic life and academia in the ‘50s, most of it taking place at the University of Iowa and later the University of Chicago.

14 The Titan by Theodore Dreiser
You’ve read Sister Carrie, sorta' maybe not. The Titan is another Dreiser masterpiece, loosely based on Charles Yerkes, the powerful and corrupt streetcar magnate who’s responsible for the Loop.

15 The Pit by Frank Norris
Finance as theatre, with the Chicago Board of Trade as the stage. This here’s a cautionary tale. Spoiler alert: lotta’ greed.

16 The Cliff-Dwellers by Henry Blake Fuller
An important "American city novel". Considered one of the first novels set among skyscrapers — Fuller's symbol for breakneck modernity, opportunism and prosperity, all in the age of Daniel Burnham.

17 Knock On Any Door by Willard Motley
A forgotten Chicago writer related to a lesser-known Chicago Jazz Age modernistKnock On Any Door follows a young Italian petty criminal into the underbelly of Chicago. It got the Humphrey Bogart treatment in 1949.

18 The Lazarus Project by Aleksander Hemon
A book about a man who wants to write a book about the real-life story of Russian-Jewish immigrant Lazarus Aauerbach, who was shot to dead by Chicago’s police chief in 1908. It’s meta. Also very fantastic.

19 1,001 Afternoons in Chicago by Ben Hecht
Before he wrote screenplays for overblown Oscar-winning melodramas (Gone With the Wind), Hecht wrote in the world of drunkards and vandals. 1,001 is a collection of short vignettes gleaned by the longtime newspaperman.

20 The House on Mango Street by Sandra Cisneros
A coming-to-age story of a Mexican-American girl named Esperanza growing up in Pilsen. Gracefully poetic, even when the subject matter is not. 

21 Boss by Mike Royko
Because no one’s comb is as thin as Royko’s. The definitive book on Daley the Elder. One comes away from this book with a deeper understanding of Chicago-style machine politics.

22 The Jungle by Upton Sinclair
The book they forced you to read in high school. The maker of vegetarians. As your correspondent’s college professor said, “a well-researched piece of journalism disguised as a novel.”

23 Rules for Radicals by Saul Alinksy
A grassroots organizing manifesto penned by a legendary Chicago community leader and activist. Could be a smidge too radical, but a highly-charged political earful that captures Chicago’s counterculture nonetheless.

24 Almighty Black P. Stone Nation by Natalie Moore and Lance Williams
An education on the notorious Black P. Stone Nation street gang born in Woodlawn in the tumultuous ‘60s. Also known as: the Blackstone Rangers


25 Complete Poems by Ernest Hemingway
A collection of poetry from a budding writer out of Oak Park. Young Hemingway did it all: parodied the greats, twisted and remixed the verses of Ezra Pound and T.S. Eliot, pondered greatly about sports and the city.

26 Chicago Poems by Carl Sandburg
Sandburg on a Chicago reading list is as inevitable as meat and potatoes. Nothing beats Chicago Poems by the lake on a beautiful summer day. Or, y'know, on your bookshelf or something.

27 Maud Martha by Gwendolyn Brooks
The Illinois Poet Laureate’s only work of fiction, set in Bronzeville. Brooks takes all “gritty” novels to task with elegant skill for prose and story that still garners contemplation on issues of race, poverty and the black identity.

28 So Big by Edna Ferber
Remember: prairie land surrounds. A story on the city versus rual debate led by a feminist heroine. Ferber's prose are really delightful. A forgotten classic, even though it was Pultizer-prize winning. 

29 Building Stories by Chris Ware
A genre-pushing graphic novel featuring 14 different works of various shapes and sizes, packaged as a box set, mostly set in a brownstone three-flat near Humboldt Park. 

30 Dining in Chicago by John Drury
A crack reporter for the Chicago Daily News, John Drury published Dining in Chicago in 1931, a highly entertaining collection of restaurant reviews and foodie meanderings on Chicago’s Depression-era dining scene. The forward by Carl Sandburg is reason alone to read it, which you can do so for free right here. Two years later, Drury would pen the official Century in Progress guide to Chicago.  

31 The Devil in the White City by Erik Larson
That one Marty and Leo are making into a movie.

32 Spinning Blues Into Gold by Nadine Cohodas
Muddy Waters. Chuck Berry. Etta James. Just a few names you’ll find in Cohodas’ telling of the improbable story of Chess Records. A must-read for any fan of modern American music, i.e. all of us.

33 A Nice Little Place on the Northside by George Will
Anyone who’s read Men At Work knows George Will’s deep-seated love for America’s pastime. The political pundit is a die-hard Cubs fan, too, and this is his ode to the ivy walls.

34 Eight Men Out by Elliot Asinof
“The most gigantic sporting swindle in the history of America!” Sports. Corruption. The 1919 World Series Black Sox. They ... gone!

35 Chicagoisms: The City As Catalyst for Architectural Speculation by Alexander Eisenschmidt
A collection of new essays and illutrations on the city's appetite for architectural greatness brought to you by the Graham Foundation. Leans slightly academic, but a fascinating read for scholars and casual architecture lovers alike. 

36 Frank Lloyd Wright: A Life by Ada Louise Huxtable
All the good, weird and brilliant trappings of FLW's life from modern architecture critic Ada Huxtable. Like, did you know: in 1914, a cook at Taliesin murdered Wright's mistress and her two children  plus five others — with a hatchet, then set fire to the home? Wild stuff. All in there.

37 Life Itself: A Memoir by Roger Ebert
The memoir that led to the movie. Sun-Times film critic. Hard-nosed journo drinking buddy. Pultizer-prize winner. The "fat one". Ebert was many things, including a damn fine writer. 

38 Yes, And by Kelly Leonard and Tom Yorton
This guidebook from The Second City inspires originality through the craft of improvisation. Inside: nuggets of improv wisdom you’d do well to implement in your daily life, told through lessons from SC workshops and behind-the-scenes anecdotes.

39 Sexual Perversity in Chicago by David Mamet
A career-making early play from the same Chicago playwright who penned Glengarry Glen Ross that explores the sexual exploits of four twenty-somethings in a post-sexual revolution, pre-AIDS era. Enough Chicago slang in here to make it feel believably local.

40 Raisin in the Sun by Lorraine Hansbury
Right now, somewhere in the city, Raisin in the Sun is being played, acted or discussed. The first play written by a black woman to be produced on Broadway, and that was back in 1959. Still poignant today.

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