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Chicago History Books for Your Holiday Gift List

By Alex Bean on November 29, 2017


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.

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

Chicago History books 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 as guide 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

Chicago history books 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.

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.

This book would be excellent to pair with a gift card for a walking tour with us. We offer our “1893 World’s Fair Tour with Bars” several times a week and it stays mostly indoors so it’s great any time of year!

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, which is where we start our Changes and Spaces in Pilsen Food Tour. It just opened up in the Fine Arts Building, which we visit during our World’s Fair Tour, 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 [email protected] or on Twitter!

– Alex Bean, Content Manager and Tour Guide


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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