Chicago, Illinois: Can’t-miss LGBTQ+ Stops and Events

The first (and only) of its kind, the Legacy Walk on Halsted Street (also known as the Legacy Project) has been curated like a museum. It’s organized into 35 (and counting) giant Rainbow Pylons whose memorial plaques honor the legacies of important figures within the LGBTQ+ community. Located in Boystown, the only officially recognized gay village in the USA, this dynamic project aims to combat anti-gay bullying and to bring LGBTQ+ culture and history to light. Stroll through this historic neighborhood, stopping to engage with each seven-meter-high pylon, learning more about both famous and lesser-known LGBTQ+ figures such as James Baldwin, Harvey Milk and Sally Ride whose achievements helped shape the world.

Every June, Chicago throws a major party, and everyone’s invited. The centerpiece event of this two-day festival along Halsted is a 6.4-kilometer parade, held the last Sunday of the month to commemorate the anniversary of New York City’s 1969 Stonewall Riots. Street fairs, marches, concerts, drag shows, plays and dance parties help usher in the parade, which includes 200 entrants. You’ll see colorful floats, dazzling marching bands and performers, and of course, hundreds of thousands of revelers enjoying the festivities. Can’t get to Chicago in June? Try August, when another two-day festival, Northalsted Market Days, unveils more music, dancing, food and general merriment.

Though also home to a proper supper club, Kit Kat’s “Divalicious” Sunday Brunch has been celebrated far and wide for its build-your-own mimosas and Bloody Marys, among other beloved brunch items. But it’s the world-famous Kit Kat Divas, stars of a raucous, rollicking drag show, who really draw a crowd here. The dinner menu is also top-notch, featuring entrees cleverly named after legendary performers. Don’t miss specialty martinis such as the Lava Lamp, Kit Kat’s Passion or Queen of Hearts, which pair perfectly with the club’s Old Hollywood décor, classic movies projected on the wall and the outstanding divas themselves, of course.

You may hear it referred to by its official name as Osterman Beach, but by either name, Hollywood Beach is the beach to visit. Located near the Edgewater neighborhood in Lincoln Park, this clean, uncrowded beach is a hot spot for the local LGBTQ+ community, especially from May to September. Hang out at the LEED-certified beach house, soak up the relaxed vibe or pick up a yummy (and vegetarian-friendly) bite at the concession stand. There’s free Wi-Fi here too, just in case you have to work while you play. If not, unwind with a stand-up paddleboard ride, or, even better, grab a pina colada from Nacho Mama’s Beach Bar.

Chicago serves as the Midwest’s major transportation hub, with two international airports offering worldwide service. Fly in to O’Hare (ORD) or Midway (MDW); both airports offer multiple transportation options into the city, including trains, shuttles and rental cars.