The Ultimate Queer Weekend Guide to Chicago

Chicago has always been a huge draw for queer travelers. It offers the best of everything with a booming nightlife scene, top-tier cultural activities, and a dash of Midwestern charm. Here’s a beginner’s guide to the Windy City, an itinerary for members of the LGBTQ+ Community that you can complete in just one weekend. It will have you coming back for more. We guarantee it!

Saturday

Morning
No trip to Chicago would be complete without a stop in the East Lakeview neighborhood of Northalsted (aka Boystown).

Walk along North Halsted Street and shop to your heart’s content at the dozens of boutique shops lining the streets. For brunch, you should consider trying the delectable Lakeview omelet at the Hutch American Bistro on North Clark Street.

To finish out the morning take a self-guided tour of The Legacy Walk, a one-of-a-kind outdoor museum walk that celebrates LGBTQ+ history and heroes.

Afternoon
After all that walking, you can quench your thirst with a beer at Wilde, a literary-themed upscale Irish pub with leather banquettes, an extensive beer list & American bar fare. Afterward, go on a neighborhood shopping spree and visit local spots like FOURSIDED, a shop that not only supports independent artisans, but it also sells handcrafted items, including frames and cards.

Evening
Check out authentically Chicagoan improv comedy at The Playground Theater. For more theatrical entertainment have dinner at Kit Kat Lounge & Supper Club. With an innovative martini and cocktail list of more than 200 offerings, Kit Kat is truly a world-class entertainment hotspot that serves upscale contemporary cuisine and Kit Kat Divas entertainment surrounded in sleek South Beach meets Hollywood-inspired décor,

If you enjoy a city with vibrant nightlife, Chicago’s more than got you covered. Check out the world-famous Roscoe’s Tavern, a long-standing gay bar and club with regular DJs, dueling pianos, and lots of drag shows. There’s nary a Drag Race queen that hasn’t sashayed her way through Roscoe’s. Sidetrack is another popular, multi-level spot with frozen drinks, a packed dance floor, and a rooftop deck. If you’re looking for tiny and casual, then The Closet will serve you well.  

Sunday

Morning
If you follow the lake north it will lead you through Uptown, Edgewater, Andersonville, and Rogers Park. Each neighborhood has its unique characteristics of course but all are recognized for their diversity and inclusiveness.

In Andersonville, head to Clark Street, where you’ll find an array of local boutiques and vintage stores. The  Women and Children First bookstore has an incredible collection of titles by female authors and hosts tons of cool literary events throughout the month such as poetry readings, book discussions, and signings. If you’re in the market for vintage fashion and home decor then head over to Brown Elephant Resale Shop — all proceeds benefit LGBTQ healthcare for the uninsured.

Afternoon
For lunch, head Uptown to the cozy daytime cafe, Tweet, for the scrumptious Crab Cake Sandwich Platter. While you wait for your table, grab a drink next door at Big Chicks, an iconic LGBTQ bar and the cafe’s sister venue.

Head to the Rogers Park neighborhood, where vacationers should consider checking out the Leather Archives & Museum. This adults-only hidden gem celebrates fetish subculture through art, artifacts, and archives. It’s the perfect stop for a kinky queer traveler.

Evening
End the day back in lively Uptown, where you can have your dinner with a side of jazz at the historic Green Mill, a Prohibition-era haunt frequented by the likes of Al Capone. You can even sit in his favorite booth. If that’s not your scene, you can check the schedule at the Pride Arts Center (PAC), a vital part of the arts environment in the Buena Park neighborhood and Chicago theater community. Pride Films and Plays organize performances at PAC, including monthly events such as play readings, film screenings, and cabaret nights.

For more travel inspiration on what to see and do on your next trip to The Windy City, visit the Choose Chicago website.