Chicago's Halsted Street: A Guide to the Best Gay Bars in Boystown

Looking for a vibrant night out in Chicago? Halsted Street, the heart of Boystown, offers an electrifying array of gay bars, each with its own unique flavor and a story to tell. Whether you're after a high-energy dance floor, a cozy neighborhood hangout, or a dazzling drag show, Boystown has something for everyone.

So, ditch the map and follow us as we explore some of the best gay bars this iconic Chicago neighborhood has to offer.

Sidetrack: The Grandaddy of Boystown Fun

No tour of Boystown is complete without a stop at Sidetrack. Open since the '80s, this sprawling complex of bars has become a landmark.

Seriously, with multiple levels and rooms, it can hold over 1,000 party-goers! What makes Sidetrack so special? Think huge video screens blasting music videos (both classic and current), an endless supply of boozy slushies, and a diverse crowd of regulars. Grab a drink, challenge someone to a game of darts, and get ready to mingle.

Sidetrack isn't just a bar; it's an experience.

Tweet: Brunch by Day, Bar by Night (and Trivia Too!)

Looking for a place that's both lively and laid-back? Head over to Tweet. This neighborhood institution welcomes everyone, but it's especially known as a lesbian bar.

But wait, there's more! Come for the trivia nights, the legendary free Sunday night buffet, and the themed dance parties. And if you're feeling a little rough the next morning? No problem! Tweet has a sister restaurant attached, serving up a delicious brunch.

Seriously, what's not to love?

Spin: Where the Night Takes a Turn

Spin has been a Boystown staple for over a decade, and it's easy to see why. This multi-faceted bar offers something for every mood. Want to show off your skills? Hit the pool tables.

Feeling anti-social? Zone out in front of the big screen TVs. Need to mingle? Head to the retro lounge. And if you're ready to dance, the dance floor is waiting. Each room at Spin is uniquely decorated, creating a distinct atmosphere. The main room, with its blood-red walls and eerie lighting, is particularly memorable.

Don't miss the techno dance floor located downstairs. And the staff? They're friendly, efficient, and genuinely seem to enjoy their jobs. Plus, Spin hosts private parties - got an event to celebrate? They have you covered. Just a heads up, the bathrooms might leave something to be desired; but hey, focus on the fun, right?

Second Story Bar: Downtown Vibes in Boystown

Craving an old-school vibe with a touch of cabaret?

Second Story is your place. While the source mentioned it as a "gay bar near downtown Chicago", it is very much in the heart of Boystown. This spot offers a variety of entertainment, including dueling pianos, themed dance nights, and karaoke hosted by the one and only Honey West.

Grab a drink and get ready to sing your heart out!

La Cueva: Dancing, Drag, and a Whole Lotta Fun

For a night of non-stop dancing, head to La Cueva. This bar is known for its regular karaoke and drag events, and it boasts a spacious outdoor beer garden.

Jam out to classic tunes on the jukebox, admire the works of local artists, and enjoy the bar's "no cover, no attitude" policy. La Cueva is the perfect place to let loose and have some fun.

Beyond the Bars: Embracing the Spirit of Boystown

Boystown isn't just about the bars; it's a community.

The owners of many of these establishments are local activists who have fought for anti-discrimination legislation and other important causes. When you visit Boystown, you're not just having a night out; you're supporting a vibrant and inclusive community. So, raise a glass to Boystown, and get ready for an unforgettable experience!

Ready to explore Chicago's gay bar scene? From legendary institutions to hidden gems, Boystown has it all.

Whether you're a local or a visitor, these bars offer a welcoming and exciting atmosphere. So, what are you waiting for? Get out there and discover your new favorite spot!