The most recommended books about Chicago

This book deals not only with period politics, 1920s Chicago, but also with the challenges faced by women of color during the period.

The main character, Honoree Calcour, was a nightclub dancer who ran afoul not only of politicians but also of the mafia. She’s being interviewed by a young filmmaker who wants to know about her life … but Honoree is over 100 years old and says she doesn’t remember much. She remembers more than she initially lets on, but that’s probably not surprising.

We have complicated characters who aren’t always likable and face uphill battles in numerous areas of their lives. All of them came to life on the page; I felt as though I knew every one of them.

Two Monogamous is the introduction to my first romantic suspense series the (Two Monogamous series).

It questions monogamy when Jarrah unknowingly falls in love with twin brothers, Dario and Dustin. One of the twins offers her romance, mental stimulation, and security, while the other offers her sensuality, adventure, and spontaneity. The two of them work together to be the perfect man for her.

This novel opened my mind to polyamory and made me question whether twins could share each other’s emotions, thus falling in love with the same person. I wrote this series to tackle issues that make relationships difficult. However, I demonstrate how creating a community can make relationships easier.

Check out the Two Monogamous series to explore poly relationships through a group of relatable characters.

This book was my childhood favorite, by far. The Girl Who Owned a City is an exploration of life after adults: when every adult suddenly dies, the world is left to their kids… and not everyone will survive. Determined to keep her younger brother alive and the memory of their parents close, Lisa somehow creates a community that becomes a safe haven for miles around. As a main character, Lisa absolutely steals the show; her resourcefulness and grit are unmatched, and stuck with me for years after reading this book. There’s also a graphic novel version, for anyone who prefers that format! 

This jive-tongued jazz cat really knows how to use language! His use of slang is evidenced by the ten-page glossary at the end of the book. Raw and gritty, Mezzrow’s memoir describes how he learned to play jazz and blues in a juvenile reformatory, where he developed his love for the Black “race” and its culture. He often riffs on race. In 1920s Chicago he rubbed elbows with Black and White jazz luminaries, plus gangsters, prostitutes, and drug dealers. During a side trip to Paris, France, he spread the gospel of jazz to Europe. In the 30s he lived in New York City’s Harlem, inhabiting a milieu similar to that in Chicago, peddling marijuana to jazz greats and others. His extraordinary writing inspired Jack Kerouac and the Beat writers.

This is the first book I ever read by a Latina author. I was nineteen years old and a student at a small private liberal arts college in Connecticut. My professor assigned it to my American Literature class. I thought she’d made a mistake because some of the words in the book were in Spanish. I didn’t know you could do that—write in English but have some words in Spanish peppered throughout the dialogue and text. I was stunned.

I remember reading about Esperanza and her experiences in her Mexican neighborhood in Chicago, meeting characters on Mango Street, and falling in love with both the story and Cisneros’ playful, vulnerable, poetic writing style. After reading this book, I knew I also wanted to be a writer.

As someone fascinated by life's "what ifs" and the paths we choose not to take, this book hit all the right notes for me.

Through Jason Dessen's eyes, I experienced every moment of his longing for the simple things we take for granted—family dinners, quiet evenings, familiar embraces.

While the story cleverly explores alternate realms through quantum mechanics, what really kept me turning pages was the very human question at the heart of the story: what would we sacrifice to protect the life we've chosen, even if another version of that life might seem more impressive on paper?

I devoured this book through two intercontinental flights—no small feat for someone who normally can't focus on anything but the plane’s slightest jiggle.

If screwball detective fiction intrigues you, you must read Craig Rice. Why not start with Eight Faces of Three, the mystery introducing the wacky, rye-soaked team of Jake Justus, Helene Brand, and John Joseph Malone?

Justus is a good-looking press agent and the book’s moral center; Brand is a gorgeous heiress and non-stop partier; and Malone is a stumpy lawyer-slash-PI with good instincts and better luck. Imagine Philip Marlowe meets the Marx Brothers.

In Eight Faces of Three, a young woman awakes to find her aunt murdered, all the house’s clocks set to 3 am, and herself the prime suspect.

Craig Rice was the first mystery writer to grace the cover of Time magazine. Her private life was strewn with ex-husbands and empty booze bottles, and she died way too young at 49.

However, her literary legacy—one critic dubbed her the “Dorothy Parker of detective fiction”—will keep her… show more.

In the aftermath of the Supreme Court’s ruling in Dobbs, I think it is imperative to remember what life was like before Roe v. Wade and what women did to survive and to live their lives on their own terms. Kaplan’s book tells the story of the Jane Collective in the words of the women who made Jane work, which makes for powerful reading. And, I think it is important to ask ourselves what about today’s post-Roe era is “like before” and what is very different. For example, pre-Roe, most state restrictions on abortion contained exceptions for rape and incest. Post-Roe, nearly all state abortion bans contain no exceptions for rape or incest. The Story of Jane also chronicles, in some ways, a freer time in which one’s every query and movement was not tracked by one’s phone. 

This book offers nuts and bolts systems and practices for thinking in new ways, organizing more effectively, and producing more abundantly. The author’s insights on establishing goals, setting priorities, and meeting deadlines are spot on. Though written a few decades ago, its lessons are timeless because they focus on reaching an endgame that provides a sense of satisfactory achievement. The author’s sense of humor and his ability to avoid tedious theory give the book momentum and energy.

Hollie’s debut novel is a combination of romantic suspense and paranormal with an interesting concept. The female protagonist is a memory surgeon in Chicago. She removes and keeps painful memories from her patients, which weighs on her psyche. Dean, a police officer, asks her to look at the memories of someone in a coma in an attempt to catch a serial killer. As the two become more and more entangled, their search for clues and growing romance, may make Kiera the next victim.

The paranormal aspect is intriguing, and the concept was completely unfamiliar to me. The book is not for the faint of heart because her depictions can be graphic, but if you like urban grit and sexy romance, this may be the book for you.