Read Your Way Around Chicago

Chicago is too big, enormous in both geography and spirit, to capture in its entirety. Locals understand this. If you find a book set in a nonspecific “Chicago” — a book purporting to take the whole place as its subject, or one that assumes downtown is the entire ethos — you know it was written by someone who only visits.

To write well about Chicago is usually to write about specific blocks, buildings or ethnic enclaves. This is the DNA of Chicago literature: neighborhood as subject, neighborhood as map of the heart.

Of course, what makes a neighborhood isn’t just the people and the map, but history. And Chicago is somewhat unique in its evident layers of time. In no other city of this size and grandeur would the one-story hardware store that’s only open on Wednesdays or the record store that sells 10 LPs a week survive into 2024. It’s possible here to turn a certain corner and forget that it’s not 1973, or 1952, or 1899. Chicago literature, too, tends to take the city’s past as part of its present. If you’re visiting in person or through books, you’d do well to read your way not only into every neighborhood, but into every era of the city.

What should I read to discover the Chicago of yesteryear?

Plenty of Chicago reading lists begin and end with the first half of the 20th century, and while I don’t love that, you could do worse than to start with this heady time when the city, in the wake of 1871’s Great Fire, was busy reinventing itself and self-mythologizing.

You can start your old-school deep dive with Theodore Dreiser’s “Sister Carrie,” a 1900 realist novel about a Wisconsin girl who comes to Chicago and gets mixed up with everything from acting to robbery.

Next, try Carl Sandburg’s “Chicago Poems,” the collection that contains “Chicago” — the one about the “Hog Butcher for the World … Stormy, husky, brawling, / City of the Big Shoulders.” Sandburg first published the poem in 1914, in Chicago’s own Poetry magazine, founded two years earlier by Harriet Monroe.

You might move on to Richard Wright’s 1945 memoir “Black Boy,” which starts with Wright’s upbringing in the South but winds up on the South Side of Chicago among 1930s Marxists and writers.

Then there’s Nelson Algren’s 1949 novel “The Man with the Golden Arm,” about a World War II veteran’s struggles in the old Polish Downtown, which was the first recipient of the National Book Award for fiction. (Although, really, my favorite thing about Algren is that his torrid affair with Simone de Beauvoir led to de Beauvoir, then 39, experiencing her first orgasm. Chicago can leave you breathless like that.)

What about the Chicago my uncle grew up in?

Let’s say you make the wise and bold move to forge ahead into the second half of the 20th century, the time when modern Chicago — with all its problems, but all its creative power — took shape.

Start with the writers of the Chicago Black Renaissance that began in the 1930s but blossomed in the mid-1950s. Any of Gwendolyn Brooks’s poetry will do you well, but “Annie Allen,” which won the Pulitzer Prize in 1950, focuses on a young woman’s coming-of-age in Bronzeville, and the novella “Maud Martha,” Brooks’s only fiction, continues its themes. Lorraine Hansberry’s 1959 play “A Raisin in the Sun,” set on the South Side, was just the beginning of what that writer might have accomplished had she lived longer.

The mysterious midcentury figure Bette Howland was all but forgotten until her selected stories appeared — after her death — in the 2019 collection “Calm Sea and Prosperous Voyage.” A divorced single mother and the sometime lover of Saul Bellow, Howland wrote about Chicago and heartbreak, and she’s one of the best writers you probably haven’t read. (You could also, of course, read Bellow’s “The Adventures of Augie March,” a fictionalized account of the author’s childhood on Chicago’s Jewish West Side.)

“Studs Terkel’s Chicago,” a Pulitzer-winning oral historian’s ode to the city, came out in 1986, and you’re obliged to read it aloud with a cigar in your mouth.

We can’t let you leave without reading Sandra Cisneros’s 1983 novel “The House on Mango Street” and Stuart Dybek’s 1990 short story collection “The Coast of Chicago,” about — respectively — a neighborhood much like Cisneros’s own Humboldt Park, and Dybek’s native Polish South Side.

What’s going on today?

Just about everything. Here’s a city big enough to hold multiple presses, universities, book festivals and dozens of independent bookstores — but unburdened by New York’s Big Publishing climate or L.A.’s “I’m also a director” vibes. In short, it’s literary heaven.

Many authors still follow that Chicago tradition of neighborhood as subject. Toya Wolfe’s “Last Summer on State Street” is a brilliant debut novel about girls in the Robert Taylor public housing project. Claire Lombardo’s “The Most Fun We Ever Had,” another spectacular debut, tackles family life in Oak Park. Kathleen Rooney’s “O, Democracy!” takes on Chicago and national politics in 2008. Alex Kotlowitz has continued the project of sociological journalism begun in 1991’s “There Are No Children Here,” his landmark story of two brothers growing up in a West Side housing project, with books such as “An American Summer,” which grapples with gun violence. Aleksandar Hemon’s “The Lazarus Project” examines, in fiction, the real murder of an immigrant teenager by a Chicago police officer in 1908.

Chicago is a genre-bending city, and many recent works carve out their own space. The four “BreakBeat Poets” anthologies published by Chicago’s own Haymarket Books include poets from all over, but deftly highlight the hip-hop/poetry/spoken word nexus that makes this the best poetry town in the country. Emil Ferris’s graphic novel “My Favorite Thing is Monsters” is part coming-of-age story, part mystery novel and part B-movie horror. (The much-awaited sequel finally arrived this spring.) “Ensemble,” an oral history of Chicago’s unique theater scene (improv meets experimental meets comedy meets highbrow meets D.I.Y.), compiled by Mark Larson, is riveting.

I’ve got two days in town. Where can I see literary Chicago?

Start your first day at the Newberry Library, the free independent research library of your Gilded Age fantasies, which is open to the public and holds everything from a First Folio to the archival records of local dance companies.

Next, head to the new-ish American Writers Museum on Michigan Avenue. While the museum is dedicated to all American writers, there’s a proud emphasis on Chicago’s homegrown authors.

A few blocks south, ride the elevator to the 10th floor of the Fine Arts Building — then wind your way through the hallways and descend floor by floor, taking in the door plaques for L. Frank Baum’s old studio, the room where Poetry magazine began and Frank Lloyd Wright’s one-time office. You’ll also hear music lessons; see a puppet studio, a violin maker’s workshop and a paperweight gallery; and smell the paint from artists’ studios. Stop on the second floor at Exile in Bookville, an indie bookstore with the coolest music selection, best collection of small press books and best views in the city. And if you happen to come on a Thursday night, you might find yourself in the live audience for NPR’s “Wait, Wait, Don’t Tell Me!” in the ground floor theater.

Day two is for the suburbs. In Oak Park, you can take a guided tour of Ernest Hemingway’s birthplace, as well as Frank Lloyd Wright’s first adult home and studio. Then make your way north to Lake Forest, where — if you’re very lucky — the storied artists’ residency Ragdale may be open to the public, with a summer dance or music performance; this is the place where, after coming for a visual art residency, Audrey Niffenegger decided to try her hand at fiction instead and came out with “The Time-Traveler’s Wife.” In the early 20th century, when it was still the private home of an architect, Carl Sandburg, Vachel Lindsay and Harriet Monroe spent time here. On your way out of town, drive by the childhood home of Ginevra King, F. Scott Fitzgerald’s model for Daisy Buchanan.

But wait, your flight was delayed! You’ve got one more hour in the city! Take your inner child, or actual child, to Oz Park, where statues of Dorothy, the Tin Man, the Scarecrow and the Cowardly Lion guard the city’s playing toddlers and remind visitors that Baum was looking out his window at a miraculous and very real city as he invented his emerald one.

Isaac Newton claimed he’d only seen so far “by standing on the shoulders of giants.” That’s how I feel as a writer in Chicago: supported and inspired by the Chicago literary tradition and its stalwart practitioners. We’re spoiled for literary giants, past and present. And this is — don’t forget it — the city of big shoulders.

Rebecca Makkai’s Chicago Reading List

• “Sister Carrie,” Theodore Dreiser

• “Chicago Poems,” Carl Sandburg

• “Black Boy,” Richard Wright

• “The Man with the Golden Arm,” Nelson Algren

• “Annie Allen” and “Maud Martha,” Gwendolyn Brooks

• “A Raisin in the Sun,” Lorraine Hansberry

• “Calm Sea and Prosperous Voyage: The Selected Stories of Bette Howland,” Bette Howland

• “The Adventures of Augie March,” Saul Bellow

• “Studs Terkel’s Chicago,” Studs Terkel

• “The House on Mango Street,” Sandra Cisneros

• “The Coast of Chicago,” Stuart Dybek

• “Last Summer on State Street,” Toya Wolfe

• “The Most Fun We Ever Had,” Claire Lombardo

• “O, Democracy!”, Kathleen Rooney

• “There Are No Children Here: The Story of Two Boys Growing Up in the Other America” and “An American Summer: Love and Death in Chicago,” Alex Kotlowitz

• “The Lazarus Project,” Aleksandar Hemon

• “The BreakBeat Poets” Vol. 1-4

• “My Favorite Thing is Monsters,” Emil Ferris

• “Ensemble: An Oral History of Chicago Theater,” Mark Larson

• “The Time-Traveler’s Wife,” Audrey Niffenegger

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