A History of Hugh Hefner in Chicago

Most locals remember that, like Hugh Hefner himself, the myth and image of Playboy was born here in Chicago. But standard trivia like that is never enough for us! So let’s take a moment to talk a little more about the story behind the man and his club. You can learn a bit more by signing up for a Downtown Bucket List private tour, of course.

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.

Hugh Hefner: Most Famous Chicagoan?

First and foremost – yes! Hugh Hefner is originally from Chicago. In the 2010 documentary about him, he says, “My roots come from Chicago. My dreams came from Hollywood.” He was born and raised by conservative Midwestern Methodist parents in Montclare, a neighborhood on Chicago’s northwest border. He earned a psychology degree from the University of Illinois at Urbana Champaign in less than three years. His 152 IQ score may have helped there. After that, he came back to the city and lived and worked here for many years before moving to LA in the ’70s.

First Foray in PublishingHugh Hefner in Chicago That Toodln' Town

Hefner’s first dabble in–what we’ll call–adult publishing was released shortly after returning to Chicago from school.  That Toddlin’ Town: A Rowdy Burlesque of Chicago Manners and Morals was released in 1951. Though the title says quite a lot, it does not say it all. This little book (that you can read online) is a compilation of comics that play off of Chicago scenes and people with some of the sophistication, sexiness, and silliness that we associate with Hefner’s other endeavors.

A few years later, during a sort of winter of his discontent, Hefner sold most of his belongings and started work on what would become the first issue of Playboy. From there, he launched a worldwide enterprise involving not just publications but also all kinds of entertainment and activism in censorship.

Chicago Sex History Playboy Hugh Hefner in Chicago

Playboy Conquers the World

Success and prosperity ensue. Hefner buys himself a mansion in the Gold Coast, where he can enjoy whatever he pleases. And if you doubt that for a even a second, just consider the famous plate above the doorbell that read, “Si Non Oscillas, Noli Tintinnare” in Latin. In English it means, “If you don’t swing, don’t ring.”

Then on leap day in 1960, Hefner opened the first of the Playboy Clubs at 116 E. Walton St.. Here “keyholders” could come to eat and to drink while enjoying big name entertainment and service from ladies dressed as Playboy Bunnies.

Hugh Hefner in Chicago Playboy sign Palmolive Building

After a few years, they move to the Palmolive Building at 919 N. Michigan Avenue, where they topped the building with nine-foot-tall letters declaring their presence.

The Playboy Legacy in Chicago

Nowadays, Hugh Hefner is so often associated with his plethora of lovers and escapades that we tend to overlook the role he played in politics and philanthropy. This man was constantly defending his First Amendment Right to the freedom of speech. Hefner battled segregation by hiring African American women as Bunnies. He also advocated tolerance of sexual preferences, including homosexuality, with the stories he published in his magazine and his lifestyle. He considered this a part of his sexual revolution to challenge the more Puritanical media of the times. Hefner even has a subspecies of Marsh rabbit named after him for his support against their endangerment.

Though Hugh Hefner left Chicago for L.A. in the ’70s, he kept the Playboy offices here in Chicago until just last year. We know that Hefner was sad to see the move happen, and so were we.  Still not satisfied? Consider viewing Playboy artifacts at the Chicago History Museum. Or learn more on a Downtown Bucket List private tour.

— Elizabeth Tieri, Chicago Detours 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.


Share on facebook
Share on twitter
Share on pinterest
Share on linkedin

be a



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

Book a chicago event

Let’s Connect!