Share on Pinterest
Share with your friends


The third largest city in the United States straddles the line between a hardscrabble, work obsessed city of neighborhoods and a flashy mecca for art, architecture, theater and food. It’s a beautiful city with a skyline that dazzles all who behold it. It’s also home to a huge LGBTQ population disinterested in coastal drama and sky-high rental markets. Heading to the City of Big Shoulders? Here are 10 things you probably don’t know about this great gay metropolis.

RELATED: 3 perfect days in Chicago

Flickr CC: Ryan

  1. Those rainbow ringed bronze phalluses lining North Halsted Street? They were erected (pun intended) in 1998 to officially designate Boystown as an LGBTQ ‘hood, making Chicago the first U.S. city to formally recognize a queer space. Today those rainbow pylons pay tribute to LGBTQ icons via biographical placards which earn the city the honor of being the world’s only outdoor museum walk.
Chicago Pride Parade, Cyon Flare, LGBTQ, gay

Chicago Pride Parade | Flickr CC by Dustin P. Smith

  1. Got Pride? Chicagoans have it, too. The Chicago Pride Parade attracts nearly one million visitors annually to the Boystown neighborhood on the last Sunday in June. It’s gotten so popular that parade officials have had to extend the route while blocking off nearby Belmont Avenue to traffic. Meanwhile, street fair Pridefest happens one week before the parade, turning the last ten days of June into a nonstop celebration.
Mayor Daley

Gay and Lesbian Hall of Fame inductee Mayor Daley | Flickr CC by Chris Eaves

  1. In 1991, Chicago became the first U.S. city to create a municipally funded hall of fame honoring the LGBTQ community. Now under the auspices of the Friends of the Gay and Lesbian Hall of Fame, its inductees include former mayor Richard M. Daley, Transparent actor Alexandra Billings, Jane Addams and many others. We’d like to thank our agent…
  1. Every spring the Chicago History Museum hosts a long-running lecture series called “OUT at the CHM” which explores the city’s vast and diverse LGBTQ history. Past events have examined everything from the impact the city’s gay bars have had on shaping the city’s queer identity to the role of President Nixon as as an accidental gay rights icon (Say, what?).
  1. When queer folks huddled in Los Angeles in the early ‘50s to form the Mattachine Society, they were actually 30 years late to the gay rights game. In 1924, Chicagoan Henry Gerber formed the nation’s first homophile organization, the Society for Human Rights. Gerber/Hart, the largest queer library in the Midwest, was named in his honor.

ALSO: Enjoy a rainbow of savings by signing up for Orbitz Rewards!

Andersonville, Chicago, LGBTQ

Andersonville | Flickr CC by Charles Carper

  1. Once referred to as “Girlstown,” adorable North Side nabe Andersonville was a one-time lesbian mecca that today is considered the city’s second queer ‘hood. Historians trace its Sapphic roots to the arrival of Women and Children First, a still-thriving indie feminist bookstore whose name inspired the oft-parodied version in sketch show Portlandia.
Hollywood Beach, gay, LGBTQ, Chicago

Hollywood Beach | Photo by Jason Heidemann

  1. Chicago likes to think of itself as the Third Coast, a nickname that is well deserved. The city is home to 28 miles of coastline, including an 18-mile lakefront trail and 24 beaches. For decades, queers sunned themselves at Belmont Rocks, but now they squeeze themselves into their tiny Speedos and hit up lovely Hollywood Beach in Edgewater.
  1. Long before RuPaul told contestants to “Sashay away,” there was the Baton Lounge which opened in 1969. The longest running drag show of its kind in the country (according to its website), the club is a bona fide city fixture that these days is a bachelorette fave, but over the years has also attracted the likes of Joan Crawford, Madonna, Kirk Douglas and yes, RuPaul. It recently moved from River North to Uptown.
  1. Want to see some kinky boots? Head up to the city’s Rogers Park ‘hood and check out the Leather Archives and Museum, the first formally organized museum in the world devoted to the collection, display and preservation of materials relating to the leather fetish and kink community. What might you see there? We can’t really say in print.

Little Jim’s | Flickr CC by Elvert Barnes

  1. Have a drink (or two, or three) at the oldest queer bar in Chicago. The current title holder is Little Jim’s, a corner taproom that opened in 1975 in what is now called Boystown. Slow to gentrify, the neighborhood was once considered so unsafe that, according to legend, patrons in the early ’80s would take cabs between Little Jim’s and nearby bar Sidetrack (a mere two blocks away).

Featured image, Flickr CC: nathanmac87

Orbitz, app, iPhone, travel, deals



Tagged: Midwest

Note: Orbitz compensates authors for their writings appearing on this site.

Jason Heidemann

Jason Heidemann

Jason is a Lead Content Specialist for Expedia Group, and manages content initiatives across numerous Expedia-owned brands. His work has been featured in the Chicago Tribune, Time Out, the Huffington Post, Chicago Magazine, Passport and many others.

Leave a Reply

Your email address will not be published. Required fields are marked *