Boystown has its own rhythm that kicks in as soon as you hit Halsted. The street stays active day and night, with something always pulling people in. You don’t have to look hard to find places that feel like a good time. Let’s take a look at a few of the things you can do while in BoysTown Chicago.

Legacy Walk –

The Legacy Walk runs along North Halsted from Belmont to Grace, with rainbow pylons marking the way. Each one features a bronze plaque honoring an LGBTQ+ figure who made a real impact—think scientists, artists, leaders, and activists.
It feels like a mix between a public art display and a walk-through history lesson. The plaques are easy to read, and if you’re curious, QR codes let you dive into more info on your phone. You can go at your own pace and take in as much or as little as you want.
It fits naturally into the neighborhood. Whether you’re out for a walk or showing a friend around, it’s worth stopping to read a few. There’s a lot of history here, and it’s presented in a way that’s both respectful and accessible.

Dance at Sidetrack –

Sidetrack is one of the most well-known bars in Boystown, and it’s always packed for a reason. The music, the crowd, the energy—it all works. You can dance, chill, or bounce between rooms depending on your mood.

The place is big. Multiple levels, different bars, and each room has its own thing going on. Some play pop hits, some play Latin, and there’s always at least one space showing music videos on huge screens. The rooftop is open during the warmer months and gets busy fast.

Every night has a different theme. Mondays are all about show tunes and singing along. Thursdays lean into Latin pop and usually include drag performances. Fridays and Saturdays are full-on dance nights with wall-to-wall people and loud music.

There’s no cover charge, which keeps the vibe laid back. Bartenders are fast, even when it’s slammed. Whether you come with friends or just show up solo, it’s easy to feel part of the crowd. People are friendly, and the space is set up in a way that makes it easy to move around and talk to people.

Sidetrack doesn’t take itself too seriously, and that’s part of why it works. You can come in for one drink or stay all night and still feel like you’re exactly where you’re supposed to be.

Eat at Las Mañanitas

Las Mañanitas sits right on North Halsted and has been a neighborhood favorite for years. It’s laid-back, easy to get into, and always delivers solid Mexican food in a setting that doesn’t feel rushed.

The menu covers all the classics—enchiladas, tacos, burritos, and fajitas. The queso fundido with chorizo comes out bubbling hot and gets ordered a lot for a reason. Portions are generous without going overboard, and everything is well-seasoned.

People come here as much for the margaritas as they do the food. They’re strong, fresh, and come in a bunch of flavors. The regular house margarita is solid, but the mango and strawberry ones are popular too.
The patio is where most people want to sit when the weather’s good. It’s open, shaded, and has enough space for groups without feeling packed. Inside, the vibe is relaxed and casual, with upbeat music playing just loud enough to feel lively without drowning out conversation.

Service is friendly and efficient. Staff keeps things moving, and even during busy hours, it doesn’t take long to get drinks or food. It’s the kind of place people stop into after work or meet up before going out later in the night.
Whether you’re showing friends around or just want a dependable spot to eat without the wait or attitude, this place holds up.

Shop at The Men’s Room

The Men’s Room on Halsted is part clothing store, part grooming spot, and fully tied into the neighborhood’s style and culture. The space is clean and modern, with a layout that makes it easy to move around and actually enjoy looking through stuff.

They carry a mix of streetwear, basics, and more niche items like leather gear and harnesses. Popular brands are always stocked, and the styles range from casual to bold. You can pick up underwear, tanks, tees, or something more standout if you’re feeling it.

In addition to clothing, they have a full section for grooming. Beard oils, skincare products, colognes, and hair care all line the shelves. It’s easy to grab what you need without having to stop at multiple stores.

There’s a barbershop in the back that does haircuts, trims, and coloring. The staff is skilled and laid-back, and they know how to work with a wide range of hair types and styles. A lot of regulars book ahead, but walk-ins are common during the week.

The store is located at 3420 N Halsted St and is open every day, with longer hours on weekends. Whether you’re updating your closet, getting cleaned up for a night out, or just browsing, it’s a solid spot to check out.

Take Selfies at the Rainbow Crosswalks and Murals

The rainbow crosswalks along North Halsted are one of the most recognizable parts of Boystown. There are 14 of them in total, stretching from Melrose to Bradley. Most are painted in the classic Pride colors, with one designed in the colors of the transgender flag.

They’re bright, easy to spot, and always draw people in for photos. During weekends and especially around Pride, you’ll see plenty of folks stopping to take selfies or group shots right in the middle of the crosswalks.
A few steps away at Halsted and Melrose, there’s a mural on the Howard Brown Health Center building. It’s bold, colorful, and was painted by artists connected to the local LGBTQ+ community. It’s become one of the more popular photo backdrops in the area.

Keep walking north on Halsted and you’ll run into another mural featuring the Bear Champ character. It’s fun, it stands out, and it adds something lighthearted to the street without trying too hard.

Have a Drink at Replay

Replay is at 3439 N Halsted, and it’s one of those bars that’s fun without being over the top. The space is filled with old-school arcade games, and you can actually play them for free. It’s easy to lose track of time between the pinball machines, skee-ball, and the fighting games in the back.

They offer a solid selection of craft beers that rotates often. There’s also a big bourbon and whiskey collection, plus a cocktail menu that changes with the season. The bartenders are friendly and know the menu well, so it’s easy to find something you’ll like.

The bar runs themed nights and pop-up events almost every week. Drag shows, costume parties, trivia, and video game nights keep things from feeling repetitive. The crowd is mixed and relaxed, with a lot of regulars.
The patio out back opens up in the spring and stays packed through summer and early fall. There’s plenty of space to sit, and the music isn’t too loud, so you can actually talk. Drinks, games, and a steady crowd keep people coming back.

Conclusion

Halsted doesn’t slow down, and that’s part of what makes it worth coming back to. The mix of bars, public art, food spots, and community landmarks gives the area a personality you don’t find everywhere. It’s easy to spend an afternoon here and end up staying out way longer than planned.