Chicago History Books for Your Holiday Gift List

It’s hard for me to imagine a better holiday gift than good Chicago history books. They hold the promise of gripping narratives, undiscovered facts, and greater perspective and understanding. It’s like manna from heaven for big ol’ history and architecture nerds, like yours truly. But which Chicago history books are worth gifting? To help you decide, we run down some of our favorites.

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1. City of Scoundrels

William hale thompson city of scoundrels Chicago history books
William “Big Bill” Thompson was the controversial mayor of Chicago during its most tumultuous days. Image via Wikimedia.

I just read this book a month ago and couldn’t recommend it highly enough. This book, written by Gary Krist, delves into the “12 days of disaster that gave birth to modern Chicago.” These days, in the dog days of the summer of 1919, sent the Windy City to the brink of civic collapse. Chicago endured everything from the fiery chaos of a blimp crashing into a LaSalle Street bank to a crippling transit strike and the city’s largest race riots. It was a fortnight of pure chaos and Krist turns it into the grist of a gripping story.

Perhaps what I liked most about City of Scoundrels how it captured the zeitgeist of that time. This was still very much a city on the make in 1919. Chicago was less than a century old, brimming with people from every part of the globe, and primed to conquer the 20th Century come hell of high water.

The personification of this time, in all its promise, hubris, and eventual stumble, is Mayor William “Big Bill” Thompson. A populist demagogue, he won office by telling ethnic Chicagoans what they’d like to hear and then ran a corrupt, somewhat hapless old-school machine one ensconced in city hall. The echoes of him in contemporary politics are obvious and unmistakable. Simply, this is one of the best Chicago history books I’ve ever read.

2. Chicago Monumental and Apparitions

fountain of time Chicago Monumental
Chicago Monumental, by Larry Broutman, is filled with gorgeous photos like this one, of the Fountain of Time sculpture. Photo by Larry Broutman.

These are two coffee table books that came to our attention earlier this year. Each are strong additions to the tradition of photo-heavy Chicago history books. Chicago Monumental, by Larry Broutman, features beautiful photography of the many works of public art and civic monuments around town. The photography, as a rule, is incredibly beautiful and captures these works in fresh, dramatic lights. I’ve seen a lot of monuments and public art in Chicago. But only rarely have I seen it look like as it does in this book.

But Broutman also delves off the beaten path and brought some interesting works to my attention. Highlights include the monument to Confederate war dead and a plaster bust of Lincoln’s head. That one is already a piece of history, in fact. It was recently vandalized and then removed from the Englewood curbside it’d sat at for decades.

chicago history books apparitions
Apparitions, by T. John Hughes, isn’t specifically about Chicago. But its images are haunting and magnificent. Image via T. John Hughes.

Apparitions is the product of T. John Hughes, who was a guest on a Loop Interior Architecture Walking Tour with me earlier this year. His book is a succession of overlaid images of past to present. A ghostly photo of a demolished building is laid upon a photo that Hughes has taken of the same spot in the present day. Chicago actually only makes two appearances in the book, but the images are lovely and fascinating. Plus, the sight of a timber-framed cottage sitting at what’s now the grand entrance of the Palmer House is startling enough to make it a recommendation for our holiday gift list.

#3. Lost Chicago

old Chicago Federal Building
The old Federal Building is perhaps the most iconic of Chicago’s lost architecture. Image via Wikimedia.

Confusingly, there are two different image-heavy coffee table books that share this title by different authors. The better (and older) one is by David Garrard Lowe. It covers the whole sweep of Chicago’s architectural history with paintings, drawings, and gorgeous photography. The city’s history and the evolution of its architecture are laid out in brief essays. This title is probably already on many shelves in the area, but that only cements its status as one of the must-have Chicago history books.

Studs Terkel Division Street America
Studs Terkel, here seen opening the Bughouse Square Debates, was a master of oral social history. Image via Wikimedia.

#4. Division Street: America

I don’t think one can fully appreciate Chicago’s history without reading Studs Terkel. He’s probably better-known as a radio and TV personality, but our own Studs was also a Pulitzer Prize-winning historian who specialized in works of oral social history. Reading his books, especially Division Street: America, is like getting a chance to converse with everyone in the city.

His books are compendiums of interviews that Studs conducted with folks from across all sorts of social, racial, and economic boundaries. People telling their own daily stories in their own words can reveal the lived truth of their historical moment. (It’s a method that recently won a Nobel Prize in Literature for the Belorussian writer Svetlana Alexievich).

Division Street was the first book that Studs wrote in this style and it remains his most famous. Taking the name of the street literally, Studs traveled down Division Street on the North Side and tried to discover the divisions that animate life in our great metropolis.

#5. The Devil in the White City

It’s impossible not make a holiday gift list of the best Chicago history books without The Devil in the White CityErik Larson’s National Book Award finalist is probably this century’s most widely-read book about Chicago. And for good reason! Larson is born storyteller who fills the book with novelistic verve and spine-tingling chills. His genius here is to wed the story of the fabled 1893 World’s Columbian Exposition with the reign of horror wrought by Chicago-based serial killer H.H. Holmes.

Larson excels at weaving these very different narratives together through thematic resonance. The reader jumps from Burnham and his cohorts while they dream up blueprints for the fair’s buildings to Holmes adding torture chambers (and worse) to his “death castle” only miles away. He subtly suggests that all our plans, be they grand or grisly, spring from the same fount of human genius. It’s a message that reverberates through the intervening decades is scintillating reading.

Worth Mentioning

There’s some other Chicago-centric non-fiction books that I wanted to mention. I haven’t gotten to read some of these and other are not purely history books. But if you see any of these books, don’t hesitate to snap them up.

In Conclusion

chicago history books the dial Chicago independent bookshop
The Dial, in the historic Fine Arts Building, is a great place to grab books off this list. Image via The Dial.

While looking for these Chicago history books, we’d love for you to patronize a local, independent bookstore during your holiday shopping. There’s been a depressing number of bookstore closing around Chicago lately, so let’s reverse that tide! There’s a great list of Chicago independent bookstores here.

But we want to give a special shout out to our friends at The Dial. This brand-new indie bookshop is run by the folks from Pilsen Community Books. It just opened up in the Fine Arts Building and is divine. Tell them that Detours sent you!

Did we miss a classic book? Overlook a must-have tome from your holiday gift list? Let us know in an email to or on Twitter!

– Alex Bean, Content Manager and Tour Guide


Chicago Detours is a boutique tour company passionate about connecting people to places and each other through the power of storytelling. We bring curious people to explore, learn and interact with Chicago’s history, architecture and culture through in-person private group tourscontent production, and virtual tours.


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

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Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
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Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
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Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
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