You’ll need more than two days to hit all of Chicago’s LGBTQ+ hotspots — but a weekend here is a good start. Whether you love the nonstop party vibe or a little Midwestern charm, Chicago’s inclusive neighborhoods offer something for everyone. Here’s how to spend a weekend exploring Chicago’s LGBTQ+ communities.
Saturday
Morning
Home to boutique shopping, vibrant nightlife, and one of the oldest LGBTQ+ communities in the United States, the East Lakeview neighborhood of Northalsted (aka Boystown) has an energy all its own.
Stroll along North Halsted Street — lined with fabulous shopping, trendy restaurants, lively bars, and energetic dance clubs — and grab some brunch at laidback mainstay Drew’s on Halsted. Fill up the rest of your morning with a self-guided tour of The Legacy Walk, a one-of-a-kind outdoor museum walk that celebrates LGBTQ+ history and heroes.
Afternoon
Enjoy elevated pub fare in cozy surroundings at Wilde (grab a leather booth or a spot by the fireplace). Then do a little neighborhood shopping at the spots like Foursided, where unusual gifts and chic decor stack the shelves.
Evening
Head to the theatre for performance art gone wild at the Blue Man Group (get ready to get messy if you’re sitting in the Splash Zone) or Chicago’s own improv comedy at The Playground Theater. Then keep the theatrical energy going with dinner at Kit Kat Lounge & Supper Club, served with a tableside diva drag show and an impressive martini list.
If you’re a night owl, there’s a dance floor calling your name. Check out Roscoe’s Tavern, a long-standing gay bar and club with regular DJs, dueling pianos, and amateur drag shows. Sidetrack is a popular, multi-level spot with frozen drinks, a packed dance floor, and a rooftop deck, and The Closet is a tiny, casual spot that’s been a neighborhood staple since 1978. Looking for more nightlife? Check out more gay bars in Chicago.
Sunday
Morning
Travel north along the lake through Uptown, Edgewater, Andersonville, and Rogers Park — all recognized as super-diverse and inclusive neighborhoods with independent shops, charming restaurants, and a dynamic nightlife and theatre scene that Chicago locals love.
In Andersonville, head to Clark Street, where you’ll find tons of local boutiques and vintage stores. Bookstore Women and Children First boasts an expansive collection of titles by female writers and features tons of cool events throughout the month. Hunt for vintage fashion and home decor at the Brown Elephant Resale Shop — all proceeds benefit LGBTQ healthcare for the uninsured.
Afternoon
For lunch, go to cozy daytime cafe Tweet in Uptown. While you wait for your table, grab a drink next door at sister venue and iconic LGBTQ bar Big Chicks. The walls are lined with the owner’s collection of original photos and paintings, making the place feel like a homey art gallery.
Continue your way north to Rogers Park for a trip into the leather lifestyle at Leather Archives & Museum. This adults-only hidden gem celebrates fetish subculture across sexual orientations through art, artifacts, and archives.
Evening
End the day back in lively Uptown, where you can take your pick from dinner and live jazz at the historic Green Mill, a Prohibition-era haunt frequented by the likes of Al Capone (you can sit in his favorite booth), or an amazing drag performance at The Baton Show Lounge, a Chicago institution for more than five decades. Or check the schedule at the Pride Arts Center, a haven for queer theatre, movies, comedy, cabaret, and more.
