When you think of Chicago, what comes to mind first? Perhaps the skyline, the food, or the sports teams. The beautiful lake, or Navy Pier. Or maybe it’s the bustling literary scene. From the stunning array of independent bookstores to places like The Newberry Library and American Writers Museum, Chicago has bookworms covered. As if that’s not enough, there’s a regular bevy of author talks and literary events, like the Printers Row Lit Fest.
I’ve spent a lot of happy time in Chicago over the years, including a stint during my college days. I haven’t visited in person since shortly before the pandemic began, but I’ve returned in my imagination many times in recent years, thanks in no small part to many of the wonderful Chicago books mentioned in this literary tourism list.
Whether these great Chicago reads call to mind memories of your own time in Chicago or you hope to travel there someday, I hope this list will make you even more excited about your next trip or provide an accessible and affordable means of escape via armchair travel.
To send you off on your literary adventure, I’m sharing twenty-three titles that I’ve read and loved or that are on my To Be Read list. (The number twenty-three is intentional; it’s Michael Jordan’s iconic jersey number.) There are plenty more books set in Chicago—and its suburbs—there’s no way to include them all here. That’s where you come in: we’d love to hear your recommendations in the comments section!
23 books set in Chicago
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Dark Matter
This fast-moving, cinematic thriller begins when the protagonist is kidnapped on his way home from meeting a friend, and is asked a strange question by his strangely familiar captor: "Are you happy with your life?" What The Martian did for space exploration, Dark Matter does for physics, and it works. Imagine the zaniness of Ready Player One, minus the video games or nostalgia trip. Crouch has said the Chicago neighborhood in his book was inspired by Roscoe Village and Logan Square. More info →
Marrying the Ketchups
A family drama centered on a close-knit Chicago family and the Irish American bar and restaurant that's been in their family for generations. It seems every Sullivan family member is at a crisis point, and the reader witnesses them working through their life-shifting career and relationship issues against the backdrop of the bar and restaurant, and the Cubs' unexpected World Series-winning season. If you enjoyed We Are the Brennans or The Most Fun We Ever Had, give this one a close look. More info →
Windfall
Alice doesn't believe in luck, at least not the good kind. But when she buys her friend Teddy a lottery ticket for his 18th birthday, she picks the good ones: 31 (Teddy's birthday). 9 (the number of years they've been friends). And for the Powerball number: 13 (the date both her parents died, 13 months apart, making her an orphan). That unlucky number wins him 140 million dollars. Teddy promises her the money won't change anything, but of course it does. A novel of love, family, fate, and Chicago, and one that you could read in the course of one happy afternoon. More info →
Hello Beautiful
The author describes her homage to Little Women as "the story of one young man, four sisters, the secrets that threaten to shatter their family, and a love powerful enough to heal it.” I fell completely in love with the Padavano family, and enjoyed seeing how the characters grew and evolved over the decades and generations. The Chicago setting was also a lot of fun. (I did so much googling for places and locations!) Readers, there are A LOT of difficult things in these pages: it might break your heart, but know that ultimately, it's a redemption story. More info →
The House on Mango Street
This modern classic is a coming-of-age almost-memoir of a young Latina girl, Esperanza Cordero, who is inventing the woman she will grow up to be. The story unfolds as a series of vignettes—some joyful, some heartbreaking—that draw the reader deep into her Hispanic Chicago neighborhood. Esperanza's observations feel at once highly specific and incredibly universal, as she reflects on growing up on Mango Street, and how she eventually wants to leave. More info →
The Devil in the White City: A Saga of Magic and Murder at the Fair that Changed America
The true story of architect Daniel H. Burnham who designed the 1893 Chicago World's Fair and serial killer H.H. Holmes. One of these things is not like the other! While Burnham navigated the recent death of his partner while planning the fair, Holmes lured his victims by pretending to be a doctor and used the fair as a cover. It’s a fascinating history of the city, the fair’s success, and the notable figures who attended. More info →
Becoming
Michelle Obama’s memoir broke literary records and it’s easy to see why. The former First Lady recounts growing up on the South Side of Chicago, meeting her husband Barack, and exactly what it’s like to watch your husband run for and then win the presidency. She shares lighthearted stories, like the details on her Carpool Karaoke appearance, yet doesn’t shy away from the hard parts of her story, such as miscarriage and the racism she’s encountered over the years. Throughout she reflects on how her experiences have shaped her and the woman she’s still becoming. A moving, inspiring, engaging read, and one that's meaningful and FUN to hear in Michelle Obama's own voice. More info →
A Raisin in the Sun
Playwright Lorraine Hansberry's award-winning drama centers on the Youngers, a Black working class family living on the South Side. After the death of the patriarch, the family wants to buy a house with the life insurance money but soon runs into discriminatory housing practices. A Raisin in the Sun is both of its time and prescient for us today. More info →
Neanderthal Seeks Human
This smart contemporary romance series follows a group of seven friends in Chicago, whose relationships blossomed thanks to Knit Night. They rally around each other no matter what's going on and their relationships continue to be a priority even as they each fall in love. In this installment, Janie, a walking fact machine, runs into Quinn, a walking dreamboat, on her very worst day. What follows is a fun and funny romance between an unlikely couple. (Closed door.) More info →
Negroland: A Memoir
The daughter of a Chicago doctor and socialite, Margo Jefferson offers an account of her experience growing up in an upper class family during the 1950s and 60s. Her privileged upbringing in Negroland (the small region where wealthy elite Black Americans lived) gave her a different lens for American culture as a part of an upper crust society that still nonetheless measured itself against white people and distanced itself from lower class Black people. She examines these contradictions as she takes readers through the Civil Rights movement and birth of feminism up to today. More info →
The Most Fun We Ever Had
I read this 500-pager in three days. This is the story of a couple married for forty years and their four grown daughters set in the suburb of Oak Park. In the opening pages, one daughter reveals a huge family secret, and the novel tracks what happens in the next year of every family member's life. Lombardo's authorial voice is gold. More info →
Monsters: The 1985 Chicago Bears and the Wild Heart of Football
Chicago boasts not one but eight professional sports teams (Bears, Blackhawks, Bulls, Cubs, Fire, Red Stars, Sky, and White Sox) and they’re proud of it. The Bears won the Super Bowl in 1985, the culmination of an exciting season that fans still talk about to this day—and not just because it unfortunately remains the team’s only championship win. Rich Cohen interviews players and coaches alike to dive deep into the magic of that winning and what they all really thought about it, including the infamous "Super Bowl Shuffle" video. More info →
The Great Believers
Makkai's prize-winning novel asks what it means to be family to one another, as the characters navigate heavy grief and loss within their tight knit communities. In 1985, Yale Tishman loves his job working in the fundraising department of a Chicago art gallery. But as his career takes off, the 1980s AIDS crisis wreaks havoc on his world, devastating his chosen family. Between chapters about Yale's life, we learn his friend Fiona's story, as she travels to Paris 30 years later in search of her estranged daughter. I loved this for its piercing depiction of the gay community in 1980s Chicago, its poignant ode to found family, and the multiplicity of fine art references that had me googling up a storm. More info →
Even Though I Knew the End
I've heard great things about this one. Helen, a warlord detective, sold her soul to save her brother’s life ten years ago and it’s almost time for her to pay up. She has the chance to win back her soul if she catches a notorious serial killer, the White City Vampire. She only has three days to do it or she’ll lose her life, as well as a future with her partner Edith, forever. A sapphic noir filled with magic, mystery, and romance. More info →
I Am Not Your Perfect Mexican Daughter
Julia could never live up to her sister Olga’s shadow and that remains true after Olga dies in a tragic accident. Instead of grieving together as a family, her mom never stops pointing out the ways Julia falls short. But it turns out Olga might not have been as perfect as everyone thought. With the help of her boyfriend and best friend, Julia starts to investigate her sister’s life to figure out if there was more to her story and the cost of being someone’s ideal. More info →
Dreams from My Father
Written well before Barack Obama contemplated a presidential run, his first memoir spans his upbringing in Kansas, Hawaii, and Indonesia to his time as a community organizer in Chicago. He explores his racial identity as he makes sense of his absentee father’s death and travels to Kenya to meet his extended family. A great storyteller, this first memoir provides a glimpse of the president he’ll become and all he’s accomplished since. More info →
Dear Mr. Knightley
Reay's debut puts a fresh spin on Jean Webster's 1899 classic Daddy-Long-Legs. Samantha Moore spent her childhood struggling in the foster care system, relying on her favorite literary characters to survive. She even expresses herself using their words when she can't find her own. Samantha's big break comes when a "Mr. Knightley" offers her a full scholarship at the prestigious journalism school at Northwestern University. The only requirement is that Sam write her benefactor regularly to tell him about her progress. Through their correspondence, Sam begins to find her voice ... but then things get complicated. More info →
Love at First
With winning characters, a multigenerational found family, and a fun Chicago setting, this romance will make a whole lot of readers happy. Will and Nora live two floors apart from each other, where late night balcony chats bring them closer together—and their clashing plans for the building spark a surprising rivalry. I expected an absorbing plot and engaging characters from this Romeo and Juliet-inspired second-chance love story; I did not expect it to get me right in the feels. (Open door.) More info →
Alone with You in the Ether
Another one I've heard great things about but haven't yet read myself. There’s no reason Regn and Aldo’s paths would ever cross. Regan is a bipolar counterfeit artist undergoing country-mandated therapy; Aldo is a mathematics doctoral student who manages his destructive thoughts by calculating time travel. But when they meet at the Art Institute, they’re drawn into a sprawling conversation about the nature of time and space and they find so much more in the process. An honest portrait of what it means to live and love when you have a mental illness. More info →
MWF Seeking BFF: My Yearlong Search for a New Best Friend
After moving to Chicago and getting married, Rachel Bertsche realizes she’s in need of local friends and decides to go on 52 friend-dates over the course of one year. While this is a memoir, the author also includes information and research about friendship. This would make an excellent book club pick: conversation starters abound. More info →
Saving Ruby King
An exploration of generational trauma and the power of friendship. After Ruby’s mother is murdered, the police decline to investigate, chalking it up to the “usual” violence of the Black South Side neighborhood. She needs her best friend Layla more than ever if she’s going to survive living with her violent father. But then Layla’s pastor father tells her to stay away from Ruby for reasons she can’t understand. Layla is determined to be there for Ruby regardless but her determination will uncover long buried family secrets that will test everything she knows. More info →
Native Son
This gritty novel wrecked me when I first read it in high school: Wright's story is raw, violent, emotionally wrenching, and utterly unforgettable. Through the eyes of Bigger Thomas, a twenty-year-old Black man living in Chicago in the 1930s, we see the extreme racial inequalities his family experiences—and how they first harden, and then desensitize Bigger. This was Wright's first novel, and on its publication in 1940, it became one of the fastest-selling novels in America's history, and remains incredibly timely today. More info →
Last Summer on State Street
This coming of age debut set in the housing projects of 1990s Chicago unfolds over the course of one summer. We meet three young girls, all about age 11, who've formed a comfortable trio and spend their summer days double-dutching on the hot concrete under the watchful eyes of their neighbors, who have all been alerted they'll soon be displaced and moved (if they're lucky) to a different apartment block. When a new girl joins their friend group the circle, instead of growing larger, is broken, and things will never be the same for any of the four, who are largely left on their own to deal with the escalating threats around them. Beautifully told and utterly heartbreaking. Content warnings apply. More info →
Which books set in Chicago have you read and loved? Please tell us all about them in the comments section!
P.S. 17 recommended reads for those traveling to Hawai’i, 12 recommended reads for those traveling to Maine (or who want to), and more literary tourism.
47 comments
I’ve called Chicago home for the last 20 years and many of these are new to me. Thanks!
Jennifer Fields’ Atomic Love. That was a BOTM selection I really enjoyed.
I love Jennifer E. Smith. Have only ever read her adult book The Unsinkable Greta James. I need to try her young adult books.
I read The Most Fun We Ever Had. And Hello Beautiful, which I liked, but felt was a bit overhyped. Too much made of the Little Women reference.
Have always wanted to read The Devil In The White City.
I would also add the Time Traveler’s Wife to this list! Love, love, Chicago!
I was going to say that too! One of my all-time favourite reads, and really made me want to visit Chicago (which I still haven’t done).
Agreed! Time Traveler’s Wife was the first one I thought of!
Such a good addition!
I love literary tourism, especially when I’m traveling to the city or state! I’m heading to Hilton Head this summer for the first time, and I’ve got “The Secret Life of Bees” and “The Southern Book Club’s Guide to Slaying Vampires” on my TBR for then.
Would take other recommendations!
I recommend Like a Complete Unknown by Anara Guard
For years I traveled to Chicago every June with my husband for the NeoCon furniture show. I always picked a book set there and then visited the sites. The Time Traveler’s Wife was rich in local setting. I also read Loving Frank and rode the train for the FL Wright tour. (I recommend even more TC Boule’s The Women.) On a Wright binge, I also suggest the YA novel The Wright Three.
You mentioned Devil in the White City. Not only is the Museum of Science and Industry, the only permanent building from the World’s Fair, a good place to visit, but Graceland Cemetery, the “architects’ cemetery” is an easy train ride, where the Palmers and Pinkerton are also buried.
Thanks for the hot tip!
I live in Chicago and was going to suggest Great Believers and Hello Beautiful but they’re already on the list :]
Some different sorts: Divergent series – post apocalyptic Chicago and Blue Balliet’s middle grade Chasing Vermeer series set mostly in Hyde Park.
Love Blue Balliet’s The Wright Three. My Girl Scout troop visited Chicago and we went to the Wright house, the bookstore, and the bakery in the book.
I grew up in Illinois and get back to Chicago as much as possible. I recommend Chicago by Brian Doyle and The Third Coast by Thomas Dyja. I love Exile in Bookville on Michigan. Unique selections and wonderful staff.
Jocelyn Green’s Windy City trilogy starts with Veiled in Smoke. Good historical fiction.
I have lived in Chicago and/or Oak Park my whole life. I have read most of these, and they are great suggestions. The Most Fun We’ve Ever Had is set on the block where I grew up!
Whoa!
Great recommendations! Also worth considering: Clark and Division by Naomi Hirahara, Then We Came to the End by Joshua Ferris, The Dean’s December by Saul Bellow, Crossing California by Adam Langer, Sara Paretsky’s mystery series, and Boss by Mike Royko.
I second Clark and Division – I loved it and wondered why it didn’t make the list – sigh, so many books, so little time. 🙂
Thirding “Clark and Division” and I was hoping somebody would mention Sara Paretsky’s crime novels! They give you such a good sense of the city. I have spent quite a bit of time in Chicago since my brother lives there (in Logan Square).
I’m an enthusiastic fourth vote for Clark and Division! Great novel. I just visited Chicago for the first time, and I loved it. Thanks for the great book list!
Living outside of Chicago, I LOVE this! Thank you, Anne, and I hope you can come and visit soon. Ditto Time Traveler’s Wife, one of my favorites!
Chicago resident here! Three Girls from Bronzeville by Dawn Turner is a fascinating memoir set in Chicago. For middle grade, I also enjoyed The First Rule of Punk by Celia Perez, and I love Chasing Vermeer and the other books by Blue Balliet – Powell’s Books (which features in the book) is a great used bookstore to check out!
My favorite Chicago book is Sin in the Second City by Karen Abbott!
Another book worth considering is ‘Maxwell Street: Survival in a Bazaar’ by Ira Berkow.
Renee Rosen has written historical fiction set in Chicago!
Yes…Windy City Blues (story about Chess Records and Chicago Blues Artists) is a great read and What the Lady Wants (story of Marshall Field).
One of my favorite books is set in Chicago: The Spoonbenders by Darryl Gregory. The story takes you from the 1960s to the ’90s and centers on the Amazing Telemachus Family. They’re well on their way to super-stardom when an on-stage mishap dooms their career. The family sort of splinters — until a series of unusual circumstances bring them back together. It’s sweet and funny and mashes up a little bit of sci-fi with the vibe of a 1930s screwball comedy. It’s frothy and has a lasting impact. Highly recommended.
Thanks for the recommendation!
Windy City Blues by Renée Rosen, which is historical fiction about the Chicago Blues scene, Chess Records, Muddy Waters, Howlin’ Wolf, Etta James, the Civil Rights Movement, etc. The audiobook version narrated by Robin Miles is also very good.
I go every year on my birthday weekend and take a dip in Lake Michigan and then walk the entire city (it seems) from end to end.
These are great books and thanks for the indie list. I will hunt a few of these down in August.
That sounds like a glorious tradition!
I’ve never been to Chicago, but I feel like I have, thru the V.I. Warshawski novels of Sara Paretsky! Everything I know about Chicago, I learned from this girl detective!
‘There Are No Children Here’ by Alex Kotlovitz
Perhaps not for this list, as I’d prefer to have travelers see the best of the city.
I live in Chicago, and two non-fiction recommendations I have that could be considered “downers” but will really help anyone understand some of the major difficulties of this city are “The South Side” by Natalie Y. Moore and “High Risers” by Ben Austen. And I strongly encourage anyone visiting Chicago to make a few stops to underrated gems on the south and west sides. Downtown, the north side, and the suburbs tend to get the most love from tourists, but there’s so much more that gets overlooked!
Hey Shaney. I’d love to hear what the underrated gems are on the south and west sides of Chicago. Can you share some of these favorite spots of yours? I prefer the road less traveled. 😉
Born in Chicago and went to college there, I love this list. I’d love to see similar ones for Denver, Nashville and more!
Most of my favorites have been mentioned but I don’t see Years of Grace. If you enjoy Edith Wharton novels, Margaret Ayer Barnes’s 1930s Pulitzer Prize winner is similar — a bildungsroman of a young, entitled woman in Chicago during the turn of the century. I loved it!
Now off to look up the Brian Doyle one that is new to me!
The Time Traveler’s Wife, as others have said. I also have discovered the Cass Raines series by Tracy Clark, about an ex-cop turned private investigator solving murders.
I grew up in the Chicago suburbs and came of age in the 90s, so I immediately got your “23” reference. I still enjoy books set in the area.
I really enjoyed “Wild Women and the Blues” by Denny Bryce. I also recently read a women’s fiction/romance set there – “The Comeback Summer” by Ali Brady.
So glad to see Dear Mr.Knightley on this list. I loved it and afterward read Daddy-Long Legs which I had never heard of and loved that too.
Sister Carrie by Theodore Dreiser for the Classics Crowd. He may have others set in Chicago, but Sister Carrie is the one I remember.
I grew up in Chicago and return often to visit friends. My historical fiction, Daughters of the Occupation (HarperCollins, 2022) is set in 1970’s Chicago— downtown and in a fictional suburb based on Rolling Meadows.
Great list!! My son is moving to Chicago this summer, so I’m excited to start reading!!
I read A Most Beautiful Thing: The True Story of America’s First All-Black High School Rowing Team, by Arshay Cooper, last year, which is set on the south side of Chicago. While not an easy read (the editing and writing could have used some work), it’s a powerful and engaging story.
I have a shelf in Goodreads entitled “Windy City”. Three authors- multiple books-I can recommend, Jen Lancaster- memoirs, Stacey Ballis- foodie fiction and Ronald H Balson historical legal mysteries.
Having grown up in rural central Illinois with parents who were tramsplants from Wisconsin, I don’t particularly *like* Chicago, so it’s not really on my literary tourism list, but I have read a few of these and enjoyed them despite the setting. 😉 It is a beautiful city, I just resent that when people think of Illinois, they only think of Chicago. There’s a LOT more state than that.
So many books set in Chicago!
A Dream of Kings, Nick the Greek, Twilight of the Ice, Ghost of the Sun, Pericles on 31st Street, and more Harry Mark Petrakis
Delilah Recovered by Amelia Dellos
White Collar Girl by Renee Rosen
The Henrietta and Inspector Howard Series by Michelle Cox
Austin Lunch by Constance M. Constant
this book just released: The Comeback Summer by Ali Brady