Deciding to relocate to a new city is a journey in itself, and there’s no such thing as too much research. However, you need to go further than simply learning about housing, the local economy and job opportunities. Oftentimes, the most successful way of getting the vibe of a place, and of deciding whether it’s a good fit for you, is by immersing yourself in its culture and history. Books and movies can tell a lot about a place. And, since we already covered the best movies to get to know Chicago, we decided to provide a list of books that will make you more intimately acquainted with the Windy City.

So, grab a book, settle into your favorite reading spot, and let’s embark on a literary adventure through the heart and soul of Chicago.

1. “The Coast of Chicago” by Stuart Dybek

In this collection of interconnected short stories, Dybek takes readers on a journey through iconic Chicago spots, such as Pilsen, Little Village and the shores of Lake Michigan. Dybek’s attention to detail and keen observation manage to immerse readers in the city’s unique atmosphere. Whether it’s the aroma of tamales wafting through the streets or the haunting melody of jazz drifting from a South Side club, Dybek’s stories evoke a sense of place that is quintessentially Chicagoan.

2. “Crossing California” by Adam Langer

Set in the racially and culturally diverse West Rogers Park neighborhood during the late 1970s, the novel provides a panoramic view of Chicago’s urban life. Pop culture references, music playlists and literary allusions offer a window into the cultural zeitgeist of 1970s Chicago. Langer’s descriptive prose brings Chicago to life, painting vivid portraits of its streets, neighborhoods and landmarks, whether it’s the bustling commercial strips of Devon Avenue or the quiet residential blocks of West Rogers Park.

Person reading a book

3. “The Time Traveler’s Wife” by Audrey Niffenegger

Set against the backdrop of the city’s iconic skyline and cultural scene, the novel offers a poignant and evocative portrait of Chicago that resonates long after the final page. The lives of its characters, Henry and Clare, are intricately weaved with the sights of the city. The historic architecture of the Newberry Library, where Henry works as a librarian, the picturesque landscapes of Lincoln Park and the shores of Lake Michigan are just some of Chicago’s landmarks readers will get acquainted with in this book.

4. “The House on Mango Street” by Sandra Cisneros

Set in the working-class neighborhood of Humboldt Park, the novel follows the coming-of-age experiences of Esperanza Cordero. Readers are transported to the streets of Chicago, from the bustling marketplace of Maxwell Street to the quiet residential blocks of Mango Street, where they encounter a mosaic of cultures, languages and traditions, highlighting the city’s diversity and spirit.

5. “Chicago: City on the Make” by Nelson Algren

Algren’s work is a collection of essays, poems and reflections painting a striking picture of Chicago’s working-class neighborhoods, marginalized communities and larger-than-life characters. Algren’s insightful characterization of Chicago as “a city that was to live by night after the wilderness had passed. A city that was to forge out of steel and blood-red neon its own peculiar wilderness” is still one of the most poetic and suggestive quotes about the true essence of the city.

6. “Chicago Poems” by Carl Sandburg

Sandburg’s poems portray the everyday lives of Chicagoans, from the factory workers and laborers to the immigrants and dreamers who call the city home. The volume’s iconic poem “Chicago” celebrates the city’s grit and determination, while “The Harbor” reflects on the bustling activity along Lake Michigan’s shores. This poetry volume is an essential read for anyone looking to connect with the essence of Chicago.

7. “The Jungle” by Upton Sinclair

Upton Sinclair’s famous novel “The Jungle” provides a stark and unflinching portrayal of Chicago’s industrial landscape and the harsh realities faced by its immigrant population in the early 20th century. Through the lens of protagonist Jurgis Rudkus and his family, we learn about the brutal working conditions, exploitation and social injustices prevalent in Chicago’s meatpacking industry. This novel did, in fact, help persuade Congress to establish federal responsibility for public health and welfare.

8. “The Adventures of Augie March” by Saul Bellow

Saul Bellow’s novel follows the Augie March, a spirited and resourceful young man growing up in Depression-era Chicago, and it highlights some of the iconic neighborhoods of Chicago as they were back then. From immigrant neighborhoods like Humboldt Park and Lawndale to the lively atmosphere of the downtown Loop, Bellow captures the energy and diversity of Chicago with beautiful prose and plenty of humor.

9. “Letting Go” by Philip Roth

While “Letting Go” by Philip Roth primarily unfolds in New York City, it features a lot of Chicago throwbacks through its main character. His interactions with fellow intellectuals, activists and residents make for a compelling lens through which to explore the city’s atmosphere. Readers will also encounter many references to Chicago’s neighborhoods, such as Hyde Park and the South Side, as well as its iconic landmarks like the University of Chicago.

10. “The Death of the Detective” by Mark Smith

This is another novel that, despite not being set in Chicago, manages to communicate a lot about the Windy City. Through the main character Vincent Valtrez’s backstory and memories, readers are provided glimpses of his upbringing in Chicago and the impact the city had on shaping his character and worldview. References to Chicago’s neighborhoods, such as the South Side and Little Italy, are also thrown into the mix.

Ready to move yourself (and your books) to Chicago? Here’s how the local self storage sector can help

If our list of books featuring Chicago helped you make up your mind and you’re now on your way to relocating here, here’s another tip for you. Chicago’s self storage sector can make the moving process, and your new life in the city, a lot easier and more organized.

Renting a self storage unit in Chicago allows you to safely keep your belongings while you are deep-cleaning or remodeling your new home to your heart’s desire. But self storage use goes well beyond the moving process. In order to keep your Chicago home or apartment neat and well organized, you can store those items you don’t use on daily basis, such as holiday decorations, seasonal items, extra furniture or books that you already read but don’t want to part ways with. This way, you’ll have the physical and mental space to start your new life in Chicago on the right foot.


Maria Gatea is a real estate and lifestyle editor for Yardi with a background in Journalism and Communication. After covering business and finance-related topics as a freelance writer for 15 years, she is now focusing on researching and writing about the real estate industry. You may contact Maria via email.

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