Best Chicago History Podcasts

I am a pretty serious podcast enthusiast, consuming hours of podcasts each week during my daily commute on the trusty ‘L.’ As a lover of all things Chicago, nothing delights me more than learning more about my city through a fascinating Chicago history podcast. I’ve rounded up recommendations of some of my favorite episodes on Chicago history podcasts for your listening pleasure.

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“Harold” – This American Life

This American Life Chicago history podcasts
No surprise that This American Life, produced at WBEZ, has a great Chicago history podcast episode. Image via Wikimedia.

Often credited as the instigators of the current podcast zeitgeist, This American Life got its start on Chicago Public Radio in 1995. It’s unsurprising then, that their take on American life has a distinctly Chicago flavor. Numerous episodes capture Chicago’s spirit, from the quirky to the heartbreaking, but the best Chicago history podcast episode is “Harold.” If you weren’t there, it can be impossible to really understand the excitement surrounding Harold Washington’s election in 1987, or the bitter rancor that plagued his first term as mayor. This episode paints a portrait of the man Washington was and the city he wanted to bring together.

Chicago history podcasts Katharine McCormick
Katharine McCormick, heir to one of the great Chicago fortunes, played a huge role in the Feminist movement. Photo via the Library of Congress.

Katharine Dexter McCormick: The Money Behind the Pill” – Stuff You Missed in History Class

On Stuff You Missed in History Class, hosts Tracy Wilson and Holly Frey dig deep to find stories and people who have been left out of the history books. This is a mission we at Chicago Detours can get behind. They’ve got a few juicy episodes on Chicago topics, but check out their story on badass woman of Chicago history Katharine McCormick. Heir of the Chicago McCormicks, Katharine made her mark on history in a big way by financing the development of oral contraceptives.

Cabrini-Green Dreams and Nightmares” – A Lot You Got To Holler

This Chicago history podcast focuses on architecture and urban design, particularly as it intersects with pop culture. What is not to love there? In Episode 2, hosts Ben Schulman and Zach Mortice take a look at the long impact of housing project Cabrini-Green. They examine how Cabrini-Green’s reputation rattled around Chicago and influenced cultural depictions of the inner city.

Bootstrapped and Proud” – The Distance

The Distance is a Chicago-based podcast that profile businesses that have survived for many years. Those that have, as they say, gone the distance. Many businesses they profile are Chicago neighborhood anchors. Highlighting these folks gives an incredible glimpse into the lives of Chicagoans who often don’t make headlines. One great example is the Alcala family, whose Western wear store has been a fixture in West Town for over 40 years.

Disco Demolition Night” – The Dollop

Listen, the 1970s were a weird, tense time. Let comedians Dave Anthony and Gareth Reynolds transport you back to one of the absolute strangest moments in Chicago history. Between a White Sox double header in 1979, local DJ Steve Dahl announced he would blow up a crate of disco records. What ensued instead was pandemonium. 

Su Lin Field Museum Chicago giant panda Chicago history podcasts
The story of this stuffed panda’s presence in the Field Museum makes for a great Chicago history podcast. Photo via Wikimedia.

Natural Habitat” – The Memory Palace

Nate DiMeo’s Peabody Award-nominated podcast creates fascinating, poetic audio portraits of unusual and surprising historical events and figures. In “Natural Habitat,” DiMeo shares the incredible story of Su Lin. She’s a panda who has been sitting, stuffed, for over 80 years at the Field Museum. What’s even more incredible is the story of Ruth Harkness. She’s the wealthy socialite who traveled to China in the 1930s to bring a live panda back to the US for the very first time. 

Reversal of Fortune” – 99% Invisible

Since 2010, Roman Mars has been on a mission to call our attention to how design shapes the world. Often, design works on us in unexpected ways. In this episode, Mars turns to a feature usually thought of as totally natural — the Chicago River. “It’s hard to tell when you see it,” Mars says, “but the river is going the wrong way.” From there he unfolds the fascinating (and disgusting) story of how and why Chicago pulled off the almost unbelievable feat of reversing the flow of the Chicago River.

Schlitz ad 1900 Chicago brewery Chicago river
A painting of a brewery warehouse on the already-reversed Chicago River. This image applies to two entries! It came to us via Wikimedia.

Schoenhofen Brewery” – Strange Brews

Craft beer is big business in Chicago, creates a lot of divisive opinions (IPAs are terrible, sorry), and brewing has a long history in the city. Strange Brews from WBEZ covers the wide world of beer in Chicago, like this episode with Ben Minkoff describing the opportunities and challenges of operating the brewery at the century-old Berghoff. They’ve also got some great deep dives into local beer history. I loved their crossover episode with Curious City. It delves into Schoenhofen Brewery, a Pilsen building shrouded in rumor and mystery. 

Chicago After (and Maybe Without) the Great Fire of 1871” – Curious City

Speaking of Curious City, it’s the grand dame of Chicago history podcasts. It would be remiss, and pretty shocking, to leave it off the list. Produced by WBEZ, Curious City tackles listener questions on all aspects of life in Chicago, from the urgent (“How Is Chicago Doing On Its Ambitious 2020 Climate Goals?”) to the more… mundane (“Where Does Your Poop Go?”) Pick any random episode and you’ll probably learn something new and interesting. Always a go-to if you’re searching for Chicago history podcasts I recommend the episode linked above that uses a thought experiment to make you look at the city in a different way. Plus, it features our dear friend Tim Samuelson, Chicago’s City Historian.

Special Thanks to Morgan Lott for her assistance with this article.

– Marie Rowley, Marketing Coordinator and Tour Guide


In business since 2010, Chicago Detours is a passionate team of educators, historians and storytellers. We applied a decade of experience as one of Chicago’s top-rated tour companies to become a virtual event company in 2020. We bring curious people to explore Chicago through custom tours, content production, and virtual events.


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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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