Best Chicago Books for Smart Holiday Gifts

The best Chicago books always make great holiday gifts. Happily, the Detours staff are voracious readers of Chicago books on history, architecture and culture, so we have recommendations for the best new Chicago books on those very topics. These selections, which delve into the city’s past and present, are just the thing for those who want to learn more after experiencing Chicago on one of our Virtual Events.

We research stories from Chicago history, architecture and culture like this while developing our live virtual tours, in-person private tours, and custom content for corporate events. You can join us to experience Chicago’s stories in-person or online. We can also create custom tours and original content about this Chicago topic and countless others.We research history and architecture like this while developing our live virtual events. Join us for fun events, like our regular general admission virtual events or an exclusive event for your private group.

Southern Exposure by Lee Bey

Southern Exposure Lee Bey Best Chicago Books
Southern Exposure by Lee Bey is a love letter to the architecture of the South Side.

I’ll start my recommendations by saying that it’s tough to surprise me when it comes to Chicago history and architecture. I often feel like I’ve learned all the big bits. So bear that in mind when I say that Lee Bey’s new book Southern Exposure: The Overlooked Architecture of the South Side included both new historical insights and photos of some gorgeous architecture I’d never seen before. Some of it, I guarantee, will come up the next time I lead one of our South Side bus tours.

Bey, the former architecture critic for the Sun-Times, is a South Side native. He sets out to document the enormously eclectic styles and sizes of the Sacred Ground‘s turf. My personal favorite is the fetching futurism of Pride Cleaners on 79th Street. Its image is now etched into my brain and I don’t know if I ever would have seen it without reading Southern Exposure.

A Shopper’s Paradise by Emily Remus

A shopper's paradise book
A Shopper’s Paradise by Emily Remus delves into the social revolution of female shopping in the Gilded Age.

Emily Remus, a University of Notre Dame History Professor, delves into a topic we explored on our Loop Interior Architecture Walking Tour with A Shopper’s Paradise. The book’s subtitle, “How the Ladies of Chicago Claimed Power and Pleasure in the New Downtown,” is the angle both her book and our tour take. The grand emporiums of State Street were not at all welcoming to female shoppers in their early days. Yet shopping in a department store would come to be seen as so feminine that Marshall Field’s constructed a separate building for the Men’s Departments in 1914. That social revolution, which still reverberates down to the present, is what Remus explores in her new book. It’s the sort of story that rarely winds up in textbooks, but has an enormous influence on our everyday thoughts and customs.

Midwest Architecture Journeys from Belt Publishing

best Chicago books Midwest Architecture Journeys
Belt Publishing’s Midwest Architecture Journeys traverses the heartland in search of its spectacular and everyday buildings.

Our friends at Belt Publishing have no quit in them. Mere months after publishing their excellent Chicago Neighborhood Guidebook, they’re back with Midwest Architecture Journeys. Edited by Chicago’s own Zach Mortice, the handsomely appointed hardcover goes off the beaten path. The book’s many writers find the glorious in the mundane and the unexpected in the everyday. They go well beyond Chicago, of course, but our city’s famed architecture serves as the focal point. I was particularly taken with the journeys which deepened my appreciation for the iconic grain silos, Sullivan’s breathtaking jewel-box banks, an examination of ruin porn, and the tallest thing in the Midwest–a transmission antenna.

1919 by Eve L. Ewing

1919 Eve Ewing Best Chicago books
1919 by Eve L. Ewing is a devastating reflection of the worst race riots in Chicago’s history.

Eve L. Ewing has been the rising star of Chicago’s literary scene for a few years now. Her two previous books, Electric Arches and Ghosts in the Schoolyard, both won year-end awards from the Chicago Review of Books. Plus, she’s a great person to follow on Twitter.

1919, a collection of poetry which reflects on the deadly violence of that year’s race riot in Chicago, should cement her reputation. Ewing uses a 1922 report, The Negro in Chicago: A Study on Race Relations and a Race Riot, as the leaping-off point. Mixing poetry, explanatory non-fiction prose, and Jun Fujita’s photos, she creates a sobering and absorbing distillation of that awful summer. It illuminates how blood spilled a century ago still cries out in the present.

Chicago by the Book from the Caxton Club

Chicago by the Book Caxton Club Best Chicago books
Chicago by the Book, created by the Caxton Club, is an encyclopedic examination of the city’s published past.

Still finding it hard to settle on a smart Chicago book despite the prior recommendations? You sound like me in Unabridged Books’ sale section. Also, Chicago by the Book: 101 Publications That Shaped the City and its Image is probably the best bet for you. Published by the Caxton Club, a Chicago-based bibliophilic society (!), the book catalogues the writings which have defined the city. It includes the stuff you expect, like The Jungle, Division Street: America, and The Devil in the White City. To my delight, the bevy of writers who wrote up these entries included myriad other forms of writing. Everything from Juliette Kinzie’s Narrative of the Massacre at Chicago to Montgomery Ward and Sears Roebuck catalogs to Poetry Magazine get their turn. It’s encyclopedic in the very best sense of the word.

Buy the Best Chicago Books at an Indie Bookstore

57th street books hyde park
57th Street Books, in Hyde Park, is one of the best Chicago bookstores. Image courtesy of the Seminary Co-Op.

As a thriving small local business we always love giving a shoutout to similar crews. Plus, indie bookstores are absolute gems and deserve all your love and support. One of the most famous indie bookstores in the whole world is down in Hyde Park. The Seminary Co-Op and its sister institution, 57th Street Books, are world famous booksellers. Founded way back in 1961, The Seminary Co-Op sells the world’s largest collection of academic tomes. 57th Street Books followed 22 years later and caters to the literary tastes of Hyde Park. Both are lovely spaces to lose yourself amidst the stacks. Though I do miss the old labyrinthine basement location of the Co-Op.

Don’t let this list of the best Chicago books be your only resource for gift buying, of course. We published our annual Holiday Gift Guide a few weeks back. You can also check out our other book recommendations.

Happy Holidays!

– 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.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


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.”
Wade K


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.”
Katie K

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.”
Shelby F

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