Chicago Gay Neighborhood History

I started thinking about how Chicago being the “City of Neighborhoods” has intersected with the city’s LGBT history. Chicago’s Boystown neighborhood made history in 1997 when Mayor Richard M. Daley designated it the city’s official gay neighborhood. It was the first such designation in American history. Chicago gay neighborhood history stretches back over a century though.

Indeed, Chicago has played a huge role in LGBT history in America. Our town hosted the country’s first gay rights organization, its first Pride Parade, and much more. I love Chicago’s LGBT History and was pleased to share a presentation on the topic as a public speaker for a corporate client recently. To celebrate LGBT Pride Month, we thought we’d look back at Chicago’s gay neighborhood history before Boystown.

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The First Chicago Gay Neighborhood?

This might be stretching the definition of “gay neighborhood” a little bit. Still, the first concentrated area where gay men and women lived or worked was the Levee. Let me set the scene: Chicago was growing like crazy in the late 19th century, the population doubling approximately every ten years. The city afforded opportunity for work, possibly for riches, and also for freedom or anonymity. Rollicking vice districts soon became a staple feature of Chicago.

The most riotous was the Levee, in the South Loop. Crooked politicians, most famously “Bathhouse” Coughlin and “Hinky Dink” Kenna, ruled the Levee. With their protection, numerous brothels, like the famous Everleigh Club, set up shop there. People who wanted something that wasn’t strictly in line with mainstream morals could find it in the Levee. Alcohol, drugs and sexy good times abounded. That meant it behooved everyone in the Levee to be discreet. Thus, it became an early haven for queer people to meet each other too. 

Gay Meeting Places in the Heart of the City

Chicago athletic association hotel cruising spot Chicago gay neighborhood history
Posh meeting spots, like the Chicago Athletic Association, sometimes became popular “cruising” destinations for gay men in Chicago.

Our next entry in Chicago gay neighborhood history may surprise you: The Loop. Though The Loop wasn’t a gay neighborhood per se, it was a place gay people could meet each other. For example, certain high-end hotels and private men’s clubs developed the reputation for being “cruising” spots where men could pick up interested men. The bar at the Palmer House Hotel was one such spot. Another was the Chicago Athletic Association, an elite private men’s club that opened in 1893. It boasted 100 furnished private rooms and a full complement of athletic facilities. (We’ve arranged custom private tours which visited both of these famous hotels, by the way.)

The Loop may not qualify as a real historic Chicago gay neighborhood. Still, downtown’s swanky hotel bars and private men’s clubs were another place where gay men might congregate.

Bohemians and the Growth of Towertown

Intellectuals and bohemians of all kinds flocked to Chicago in the 1910s-20s, and many settled in the neighborhood around the Water Tower, roughly Old Town today. Back then this neighborhood was called Towertown. It was filled with artists lofts, rooming houses where single men and women could afford to live on their own, small cafes, night clubs and bars. It was the home of the famous Dill Pickle Club where anyone with an interesting opinion could take the stage, openly discussing topics like homosexuality.

In this Bohemian district people were radicals and freethinkers. They were espousing anarchy, free love, atheism (gasp!), all kinds of beliefs that were way outside the status quo, so it naturally became a place where gay, lesbian and gender nonconforming people could live openly too.

Dil Pickle Club Towertown Chicago gay neighborhood history
The Dil Pickle Club, the crazy heart of Towertown, was also a hub of Chicago’s nascent LGBT community. Image via Wikimedia.

By the ‘20s, most Chicagoans recognized Towertown as a gay neighborhood. It hosted a collection of gay bars or tearooms like the Wind Blew Inn and the Green Mask. In these places, gay men and women could feel comfortable to be themselves and to meet each other and form a community. Middle and upper class Chicagoans looking for a wild night out would drop into Towertown to visit these establishments, which often had drag queen entertainers in the evenings.

South Side LGBT History

Bronzeville on the South Side of Chicago also had a significant and visible LGBT presence in the 1920s and more strongly into the 1930s. LGBT African Americans were often prominent and widely accepted members of their community. Just like in Towertown they often found work as entertainers and in the nightlife district. Drag balls were huge community events, especially the annual Halloween drag ball. Drag queens like the Sepia Gloria Swanson entertained nightly in clubs up and down “The Stroll,” supporting themselves throughout the hard years of the Great Depression. Male impersonators like Gladys Bentley were popular entertainers in Bronzeville too. Very little of The Stroll is left today.

Chicago’s Gay Neighborhood History on the North Side

The mid-twentieth century was a difficult chapter in Chicago gay neighborhood history. During the 1940s-50s, many gay and lesbian bars opened in the city. At the same time, the police and city politicians began increasingly harsh crackdowns on these establishments and their patrons. The Near North side became the center of newly-forming gay neighborhood, in the area around Clark, Diversey and Broadway. Another, smaller gay neighborhood developed in this time around Dearborn and Division.

Mafia figures owned most of these bars in the 1940s to ’60s. They knew who to pay off and regularly dealt with customers who needed discretion. From time to time, though, politicians or the police would feel pressured to “do something” about alleged morals issues in the city, and stage raids on the gay and lesbian bars. (It was a police raid like this on the Stonewall Inn in New York that sparked the famous Stonewall Riots.) Gay, lesbian or gender nonconforming people were also subject to harassment, arrest, discrimination in most aspects of their lives too, from housing to employment or simply walking down the street.

Despite these persistent threats, the gay community continued to grow more visible and vocal throughout the following decades. By the 1970s, the Gay Liberation Movement was in full force and the city backed down from the unfair bar raids. The gay neighborhood shifted slightly north in the coming years, with the first gay bar opening on North Halsted in 1975. The area soon picked up the nickname “Gay Town” which eventually morphed into “Boystown.”

Jane Byrne Pride Parade Boystown Chicago gay neighborhood history
Jane Byrne was Chicago’s first mayor to ride in the annual Pride Parade in Boystown. Photo via Wikimedia.

The Future of Chicago Gay Neighborhood History

When the rainbow pylons of the North Halsted Legacy Walk were installed, it was a clear indicator that the gay neighborhood of Chicago was at last here to stay. The days of being pushed around were past. That being said, no neighborhood’s future is ever certain. Some have questioned its inclusivity in recent years and pointed to how changing demographics in the district indicate that fewer and fewer gay people actually live in Chicago’s designated gay neighborhood. As the overall city has become more welcome and open to queer people, other neighborhoods may lay claim to being another Chicago gay neighborhood, while some may say there’s no need for a specific gay neighborhood at all. What is clear from surveying Chicago gay neighborhood history though is that LGBT Chicagoans have always shown resiliency in creating spaces to be themselves and find community.

– 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.

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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.

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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.
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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.

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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.
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