Chi-Town Won’t Let Gay Travelers Down

From the Legacy Walk to the Leather Archives, the Windy City boasts plenty of LGBTQ attractions.

By Joanna O’Leary

The reason why the lyrics to “My Kind of Town, Chicago Is” resonate almost universally is that the Windy City’s staggering number of cultural, culinary, historical, and sports venues make it appealing to many different types of people.

This includes Chicago’s LGBTQ community—or rather communities, as the city is regularly ranked in national reviews as one of the most diverse and gay-friendly in the country.

Thus, in addition to hitting all the must-see sights (Millennium Park, Wrigley Field, the Art Institute), it also worth seeking out spaces of significance developed by Chicago’s LGBTQ residents and allies, but enjoyed by all.

At least two days of your itinerary should be devoted to faffing about in Boystown, one of the country’s most robust LGBTQ neighborhoods. Get educated while getting in your 10,000 steps by following the route of the Legacy Walk, the world’s only outdoor museum trail dedicated to highlighting LGBTQ historical achievements. Comprising one long loop around North Halsted, the Walk features plaques and monuments outlining significant events such as the Stonewall Rebellion, and pays homage to past and present gay icons and community leaders such as James Baldwin, Frida Kahlo, Harvey Milk, and Audre Lorde. For additional details on the design and development of the Legacy Walk, schedule a formal tour.

For a reprieve from the heat or the chill (depending on when you visit), head inside the Center on Halsted, which—in pursuance of its mission to “advance community and secure the health and well-being of the LGBTQ people of Chicagoland”—offers wellness programs, support groups, medical assistance, and other social services. Stroll through the art gallery, join a pickup game of basketball or, if you have kids, enjoy a story hour. The Center is also home to the Hoover-Leppen Theater, which hosts LGBTQ-themed productions and Sunday religious services.

Fuel up for your nightlife fun at Rollapolooza, a hip sushi spot that specializes in creative maki, temaki, and urmaki. Italy meets Japan in their hearty Crunchy Melt (shrimp tempura, cucumber, and cream cheese topped with unagi, melted mozzarella, and eel sauce) while the Summer Roll with whitefish, tuna, asparagus, avocado, and diced fruit is a refreshing combination of piscine protein, vegetables, and citrus that is perfect for the sweaty season.

There is no dearth of quality bars, lounges, and clubs in Boystown, but one necessary evening stop is Sidetrack. Founded in 1982, Sidetrack has tripled in size over the years to accommodate the crowds game to try their frozen drinks and inventive shots while taking in comedy shows, sing-a-longs, pet-friendly gatherings, and LGBTQ storytelling.

Cure any resulting hangover after your evening out with brunch and some hair of the dog at Ann Sather, a 70-year-old BYOB Swedish restaurant. While it’s acceptable to satiate with standard morning fare such as their eggs benedict platters and breakfast wraps, you’re missing out if you don’t order the light-as-lace Swedish pancakes served with tart lingonberries, the succulent Swedish meatballs, or the flaky potato pancakes with applesauce and sour cream. All entrees come with your choice of two sides, and only fools pass on the oversized, delectably doughy cinnamon rolls.

While Boystown is the cat’s pajamas, don’t confine yourself to this neighborhood because big, beautiful Chicago holds many other gay-friendly attractions. Even if distressed animal skins don’t turn you on, The Leather Archives is very entertaining and informative with its well-researched exhibits displaying various milestones in the development of leather culture.

Or, you can skip the leather in favor of lace and feathers by reserving seats at the classy and sassy Kit Kat Lounge and Supper Club. One of Chicago’s most popular drag theaters, the club hosts multiple shows each night that involve tableside performances by talented resident divas. In addition to over 40 creative martinis such as the Hawaiian Punchout (vodka island passion liqueur, sour mix), the Kit Kat offers a solid array of celebrity-named entrées. Standouts include the Oscar Wilde, (a tender filet mignon crowned with a lump crab cake and dressed in béarnaise sauce) and the Mae West (fried chicken atop a cayenne maple glazed waffle with mashed potatoes, collard greens, and piquant banana horseradish puree). For a more casual but equally enthusiastic watering hole, head to Big Chicks, which has been serving its boisterous clientele cocktails and above-average bar grub (try the potato skins) for over 30 years. Enjoy the rotating collection of wonderful local art, take advantage of the excellent daily food and drink specials, and join in partying with the regulars on any of their theme nights (Bears, DJs, Trivia, etc.).

This article appears in the August 2017 issue of OutSmart Magazine.


Joanna O’Leary

Joanna O’Leary is a regular contributor to OutSmart Magazine and a freelance food and travel writer based in Houston. Her exploits are chronicled on
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