Boystown neighborhood guide

Where to eat, shop and other things to do in Chicago’s Boystown neighborhood.

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I’ve experienced many a fun night in Boystown. When I go, it’s with a group of friends to let loose, knowing the evening will be full of positive vibes.

It’s easy to navigate with plenty of transportation. It’s walkable so we can bar hop without the hassle of going far, usually just next door. And it’s a safe, hate-free district. (Well, there might be some judgment about your outfit, but mostly it’s just compliments.) As a straight woman, I know it won’t be about me, and there’s extra freedom in that feeling to just “be me.”

That feeling “to be myself” is exponentially amplified for my LGBTQ friends, many of whom have yearned for a place where they feel so welcome that not one ounce of their being has to be hidden away. It’s a place where they can put their guard down, a “home away from home,” where they feel validated.

History of Boystown

The core of this micro neighborhood in East Lakeview is Halsted, Broadway, Belmont and Irving Park. Gay Chicagoans started to move to the area in the the 1960s and 70s.  In those early years, it was called “New Town” and then in the 1980s the name “Boystown” took hold.  The city designated it an official gay village in 1997- the first ever such designation in the U.S.- and then the rainbow pylons went up in 1998.

Now those iconic rainbow pylons and flags mark an entertainment, shopping and dining district unlike any other in the the city of Chicago, if not the world.

While there are many other friendly gay enclaves in our city, Boystown has the highest concentration of LGBTQ-owned businesses.  Of the 200 that make up the Northalsted Business Alliance, the majority are LGBTQ-owned.

The Pride Parade is one of Boystown’s biggest events each year. | Rick Majewski/For the Sun-Times.

The Pride Parade is one of Boystown’s biggest events each year. | Rick Majewski/For the Sun-Times.

“What’s unique about the neighborhood is that LGBTQ people have a stake in the neighborhood. Both financially and culturally, it’s a safe space to live, work and play,” said Chad Honeycutt, Executive Director of the Northalsted Business Alliance.

“We are geographically in a place where we are a hub for all of the Midwest,” said Honeycutt. “We act as a beacon for young LGBTQ people to come visit and explore. So for me it’s an all encompassing space.”

The Northalsted Alliance is a non-profit that supplements marketing efforts to help the businesses in Boystown succeed, along with throwing several epic events and celebrations. Another significant feature that Honeycutt is truly excited about is Boystown’s hopeful, soon-to-be designation as the first officially-designated gay historic district in the country. (It’s unclear whether the historic landmark status will apply to the Legacy Walk – more on that below- or the entire neighborhood.)

Being designated an historical district is a far cry from how the neighborhood was viewed when Mark Liberson first started coming to Boystown, which was often referred to as the “gay ghetto.”

“The history was (the gay community) would go into areas that were less developed, where there was more crime, and we would start to develop them and make them our own area,” said Liberson.

Liberson is behind the management group LKH, which owns popular bars Hydrate, Elixir and Replay Beer & Bourbon. He recalled how the gay community had been relegated to different parts of the city, but property ownership made all the difference in establishing the Boystown we know today.

“The difference is that rather than being pushed out of this area,” said Liberson, “Here, people bought in. We own this building for example (and so do others). We’re not going anywhere.”

With all of the entertainment and restaurant amenities in this vibrant neighborhood, real estate prices have gone up. Add to that the accessible public transportation, walkability, shopping and good neighborhood police presence for safety results in a hot housing market for renters and buyers. Plus, there’s a great school- Chicago Public School’s Fine and Performing Arts magnet school Nettelhorst (from preschool to eighth grade)- highly coveted by young families!

A statue at The Nettelhorst School in Boystown. | Colin Boyle/Sun-Times

A statue at The Nettelhorst School in Boystown. | Colin Boyle/Sun-Times

“The genesis of our community is about acceptance and equality. We’ve always been a really welcoming and accepting community. We want people to be a part of our lives. We want families to enjoy the strip as much as somebody coming in to have a few drinks or enjoy a festival,” said Honeycutt. “We always try and preserve our cultural identity and also be incredibly welcoming.”

Liberson sees the changes in the neighborhood as a part of life’s continual evolution and as mostly positive, with more racial diversity and more patronage of businesses by straight men and women.

“Looking back to when I was in college, and when I first came to this community, I think it’s better now than it was then. It’s safer, it’s more interesting, there’s more to do. And the people are just as great as they were then. And actually they’re more comfortable. They’re able to be out in the open,” said Liberson.


Liberson recalled most bars didn’t have windows in their storefronts. “Why? Because you didn’t want people to know you were gay. You felt in danger. It was a totally different world. Now we’re comfortable being who we are, walking and holding hands, communicating freely about (our) lives. We’ve come a long way!”

Center on Halsted

While the demographics of Boystown may be changing, there is one constant anchor in the neighborhood that ensures it always remain a beacon for the LGBTQ community. Center on Halsted has roots back to 1973, when it was known as Horizons Community Service.

Center on Halsted is the largest comprehensive community center in the Midwest focusing on LGBTQ community health and wellness. Along with providing assistance with physical and mental health, there are exercise and vocational programs, plays, art exhibits, lectures and seminars. There is a technology center, gym, theater and a public roof garden. The lobby is connected to a Whole Foods, and it’s a great place to meet a friend or have a quick meeting.

Center on Halsted in the Boystown neighborhood of Chicago. | Colin Boyle/Sun-Times

Center on Halsted in the Boystown neighborhood of Chicago. | Colin Boyle/Sun-Times

For 11 years, the center has been serving the LGBTQ community of all ages, from youth to seniors, at its location at Halsted and Waveland.

The Center provides comprehensive services for HIV/AIDS and other sexually transmitted diseases. They administer “walk-in” hours for rapid HIV testing to on-going support and education through fully trained staff. The services are free and confidential and they ensure the most current and medically accurate information.

The center administers specific programming aimed at LGBTQ women with programs for women, by women. In addition, there are resources and programs for victims of hate violence and those who need legal help.

Born in Puerto Rico but a lifelong Chicagoan, Modesto Tico Valle remembers when the gay community was centered in the Gold Coast and then moved to Old Town. Escalating rent costs drove the community to its current location.

Valle, the CEO of the Center, said more than 1,400 people come through the lobby doors every day. His mission is to ensure that displaced residents, homeless youth and members of the community who are on the fringes have a place to turn.

“Our next priority is to head south and to serve our young people in the Woodlawn community more,” said Valle. “We are asking: How do we mentor? How do we lift up our communities of color, our brothers and sisters who have been forgotten and left on the fringe and empower them.”

A multi-generational community

Another vulnerable component of the LGTBQ community are seniors. Each week, more than 150 seniors, over age 55, participate in senior programs, workshops, take classes, share a meal or make new friends at the Center on Halsted.

Multi-generational supporters of same-sex marriage gather in Boystown after the Illinois General Assembly passed a marriage equality bill in November 2013. | Getty Images

Multi-generational supporters of same-sex marriage gather in Boystown after the Illinois General Assembly passed a marriage equality bill in November 2013. | Getty Images

There is affordable senior housing next door. The Town Hall Apartments was opened in 2014, in partnership with Heartland Alliance. It’s Chicago’s first LGBTQ friendly senior housing. There are 79 units of studios and one bedrooms at full capacity.  The need is so great, there is an extensive waitlist.

Pat Cummings, 65, is a resident of Town Hall Apartments. The former photojournalist now runs a pet care business.

“If you walk through the hallways, you would understand how important it is because people don’t have to be hidden about who they are deep down, what they are, they can be proud of it, they have support here,” said Cummings.

“I don’t think anyone that’s in this building right now would be able to live in Boystown; it’s much too expensive to live here and several had to sell their condos because it got too expensive. I’ve heard some of their stories, when their partner passes, they had to sell. They had to leave the home they felt comfortable in since the late 70s and 80s.”

Cummings has seen a lot of changes in Boystown, having first arrived in 1982. She remembers hanging out in the lesbian bars during that time: Ladybug, Swan Song and Augie CK’s. She described how the movers and shakers on the political scene would meet in cafes and plan demonstrations or disseminate information. During the AIDS epidemic she knew 300 people that lost their lives to the disease, including her brother.

Cummings has a wealth of knowledge and history to share. One of her favorite stories is that the Town Hall Apartments was formerly Town Hall Police Station. Built in 1907, the police station was a symbol of police discrimination in the 1970s and 80s when police raids were commonplace on gay establishments. Many of Cummings’ neighbors were booked and placed in Town Hall’s jail during that time of over-policing and discrimination.

Cummings said the center ensures she has money leftover to enjoy her life and helps keep her connected.

“(It’s) my way of keeping in contact with the younger generation,” said Cummings. “I don’t think they understand what we actually did and what we went through in order to create what they have… It’s important to keep us here because we are the shoulders that they stand on. And we stand on shoulders who came before us. This way we understand and point out, how things were, where they were, what their own history is.”

The rainbow pylons and Legacy Walk

The Legacy Project’s mission is to highlight LGBTQ people who have contributed to world culture and advancements.

Boystown is home to the only outdoor LGBTQ museum. The city has proposals to designate it a historical landmark. In 2012, the Legacy Project commenced installing placards of LGBTQ history makers on Halsted Street’s already existing rainbow pylons. New ones are added every year.

It spans a half-mile of Halsted Avenue, from Briar to Grace, on both sides of the street. The bronze placards display a photo and biography of the featured honoree. The goal of the walk is to encourage and inspire anyone who visits Boystown, particularly young people who may be bullied because of their sexual orientation or gender identity. The project has guided tours for high school field trips, professional association outings and the general public.

“It means so much to let younger people know, that are coming behind me, (about) their history. To see all those people that look just like you, and they have contributed so much to our collective history, it makes you feel proud,” said Renauda Riddle, treasurer of the Legacy Project.

The historical moniker “Boystown” may have turned off and seemed unwelcoming to women in the past, but Riddle said “a lot of bars are making sure they are welcoming every part of our community and that everyone feels welcome. They are doing a better job than in the past. And there’s a lot of progress.”

Chad Honeycutt is excited about the possibilities of the historical designation and to have the past inform the future. The Executive Director of the Halsted Business Alliance said, “For me, I’m incredibly lucky to have a board of directors that have been on the street for more than 30 years. If I forget something, I have a reminder.”

And there is a concerted effort from community members to reach every community represented in the abbreviation’s initials of LGBTQ. “We want the programming from our businesses that make sense for every single person from our entire rainbow to come to this street and know there’s a place for them and that something that interests them is happening,” said Honeycutt.

Where to hang out in Boystown

Sidetrack is the iconic place for Chicago Boystown. Boystown is built on the foundation of gay bars. Sidetrack opened in 1982 when no support organizations or community centers existed in the LGBTQ community.

“For many people the gay bars were designated community centers,” said Sidetrack’s Brad Balof.

Balof has worked at Sidetrack for 17 years and is now manager. There are multiple bars and a rooftop deck where you can order Sidetrack’s famous alcohol-spiked slushies. Videos screens are everywhere.

Sidetrack Bar was one of the first LGBTQ bars on Halsted Street. | Sun-TImes Archives

Sidetrack Bar was one of the first LGBTQ bars on Halsted Street. | Sun-TImes Archives

Active community business owners, activist and philanthropists, Jose “Pepe” Peña and Art Johnston, founded Sidetrack. Balof said it was small back then, just one storefront, with people “sitting on cases of beer boxes because there wasn’t enough space in the coolers in the back.”

Co-founder Pepe Peña decided it would be a great idea to play music videos on the screens at the bar. From music to comedy and movies, Sidetrack still continues to play videos and patrons flock in to watch and sing along to them.

“It’s something that’s really changed over time, because now we can pick up our cell phones,” said Balof, “But there’s something to be able to watch it in a large group, sing along, there’s a very communal feel about that you can’t get on your phone.”

In addition to show tunes, Sidetrack does a monthly story telling event, similar to the “Moth,” where eight story tellers share a ten-minute story.

Sidetrack hosts numerous LGBTQ community group events. | Sun-Times Archives

Sidetrack hosts numerous LGBTQ community group events. | Sun-Times Archives

There’s a wide array of daily events with show tunes as an anchor. Each format is different, so be sure to check Facebook and the bar’s other social media pages.

Kit Kat Lounge & Supper Clubis another “must see” in Boystown. Kit Kat was opened in 2000 by owners Ramesh Ariyanayakam and Edward Gisiger. Kit Kat is known for its drag shows and martinis. There are more than 200 original cocktails on the menu, of which 100 are martini flavors.

The famous Kit Kat Divas perform every night and during Sunday brunch. The gorgeous female impersonators perform in the dining room every 20 minutes throughout the evening and during Divalicious Brunch Sundays.

Where to eat in Boystown

Yoshi’s Café has been an anchor in Boystown for 36 years. Serving Japanese and French-inspired cuisine, they’ve wowed residents and visitors with eclectic cuisine and great service. Opened by husband-and-wife team Yoshi and Nobuko Katsumura, the two have often given back to charity and held events to raise money for good causes throughout the years. Yoshi passed in 2015, but his wife continues his legacy.

Wood is modern, sleek and great for a date night. Here, you’ll find small plates and happy hour, in addition to dinner. Since opening in 2013, it has continued to impress and remain a neighborhood favorite with a changing, seasonal menu and wine selection. There’s also a sidewalk patio with great ambiance. It’s perfect for people watching!

Chicago Diner has been a Chicago favorite since 1983. The vegetarian restaurant has done so well that husband-and-wife team, Chef Jo A. Kaucher and Mickey Hornick opened a second location in Logan Square and published a cookbook.

The Chicago Diner in Boystown . | Colin Boyle/Sun-Times

The Chicago Diner in Boystown . | Colin Boyle/Sun-Times

Nookies Tree is one of four locations in Chicago. A family-run business with humble roots, the founders were Greek immigrants. The Boystown location has been open since 1985. It’s BYOB and open from 7am to 3:30pm.

Lark restaurant has salads, burgers, totchos and Neapolitan pizzas. The menu is varied so everyone in your group should find something they are craving! They have a fun girls night out package where a meal includes tickets to see a drag show at Hydrate.

Other dining options in Boystown:

On Broadway, there’s:

Bars, shopping and more

Boystown is known as an entertainment district above all else! Besides Sidetrack, local favorites for dancing include Roscoe’s Tavern and Hydrate. These venues do a fantastic job of bringing in national talent to headline on their stages or D.J.

For a well-crafted cocktail, go to Elixir.

For a sports bar, head to The North End.

If you want a little less action action, head over to The Closet or to Wang’s on Broadway.

Art on display in The Leigh Gallery in Boystown . | Colin Boyle/Sun-Times

Art on display in The Leigh Gallery in Boystown . | Colin Boyle/Sun-Times

For shopping, don’t miss the Men’s Room. You can find hilarious t-shirts, quality underwear and just the right leather accoutrements that can be customized for you!

There’s also CRAM Fashion with high-end men’s fashion including Superga, RVCA, Herschel and Hudson. You’ll find everything from shoes and underwear to travel accessories and custom t-shirt lines.

If it’s art with a local focus you’re looking for, The Leigh Gallery won’t disappoint.

For gifts and stationary, I like Noteworthy Notes and He Who Eats Mud. For a gift for someone who has a sweet tooth, there’s Windy City Sweets. And Unabridged Bookstore has been a veteran bookseller in the neighborhood specializing in LGBTQ titles.

Parades and festivals

Market Days is the largest street festival in the Midwest and runs from Addison to Belmont on Halsted. Held in August, it includes four dance stages and 200 vendors. People fly in from all over the country to attend. Be prepared to see a lot of shirtless men and have a good time.

Pride Fest is held before Chicago’s Pride Parade in mid-June. There are four music stages, national headliners and more than 100,000 people attend the two-day festival. This festival is all about community engagement and raising money for LGBTQ organizations like AIDS Foundation of Chicago and Center on Halsted.

The Pride Parade began in Washington Park in 1970.  Newspaper coverage of the event says that just 150 people attended.  The annual pride celebration moved to the Boystown area in the 1980s and now attracts upwards of one million spectators. Many of Chicago’s largest businesses, civic organizations, schools, religious organizations, politicians and media companies as well as local bars all participate in the parade each year.

There’s also the Northalsted Halloween Parade, a tradition for 30 years. It’s basically a giant costume contest to see who has the most “creative funky cool costume.”

To chase away the winter blues, there’s the Frost Fest in February. The neighborhood celebrates “almost getting through winter” with a 5,000 square foot tent and local Chicago craft beer vendors and ice carvings!

In addition to this edition of The Grid, another great source for information on what’s happening in Boystown is, a locally run website with the who/what/when/where and how of everything Boystown.

What residents have to say

Victor Salvo has been a gay activist for 35 years and is the co-founder and executive director of The Legacy Project, which runs an youth education and anti-bullying program and also manages the Legacy Walk outdoor museum. He shared with us some thoughts on Boystown:

Victor Salvo. | Provided

Victor Salvo. | Provided

“As one of the last surviving “gayborhoods” Boystown, to me, represents a last great hope to have a place to call our own – permanently. I know that a lot of straight people, baby strollers and all, now live in the area and that many LGBTQ people do not. But every community needs to have a “center” – a place to anchor itself around. Because place is very important to us.

“LGBTQ people are born into a “reverse diaspora” – scattered to the wind, part of every community, every people, every race, every nationality every culture, every economic status. But separate from people like ourselves. We come together – some traveling great distances – to find people like us. And when we do we establish places where we can be safe and express ourselves, our art, our talent, our views, our ideas. We create stores, businesses, and nightclubs – whole gayborhoods.

“Boystown is one of those places. But unlike so many others that are dissipating due to gentrification, most of the real estate here is owned by the people who manage those spaces. We did more than inject life and culture here. We made it our own. So even if people live elsewhere and no longer need a “gay ghetto” the way we once did, they will still come here to experience a level of freedom and shared cultural reality they will not get anywhere else.

“With institutions like Center on Halsted, the Legacy Walk Outdoor Museum, the LGBT Senior Residence – and now with the impending designation of the Northalsted Rainbow Pylon Streetscape as a bona fide “Historic Landmark” – Boystown will be statutorily protected as an LGBTQ nexus of business and culture in a way that places like the Castro and the Village are not. We are here to stay. And I am damn proud and grateful to be a part of it.”

Bryan Smith is a VJ (video jockey) at Sidetrack Chicago. Here are his five favorite things about Boystown:

Bryan Smith. | Provided

Bryan Smith. | Provided

  1. Sunday Funday in Boystown is a must. A great way to start the day is with Brunch at Kit Kat Lounge and the amazingly entertaining Madam X. She will wow you with her Diva impersonations and performances. Seriously, you will think you’re in the presence of Gaga, Cher, Kylie, Madonna, and every other Pop Queen. The looks come fast and polished to perfection.
  2. My favorite go-to for food is DS Tequila. DS specializes in Tex-Mex goodness, great music and a fabulous outside patio. I recommend the quesadillas, salads and the best Chicken Tenders in town (get the Ranch dipping sauce – it comes with a kick!). Definitely start with the chips and salsa (3 varieties!).
  3. My favorite after-hours dance bar on the Halsted Strip is Hydrate. It is open till 4am weekdays and 5am Saturdays. Great music, fab light show and friendly staff and management team.
  4. LGBTQ history has been virtually erased, and we are rightfully reclaiming our past. The Legacy Project is a wonderful way to learn more about the many LGBTQ contributions to society.
  5. No visit to Boystown is complete with out getting Sidetrack’d! Sing out loud 3 times a week to Show Tunes, hang out with friends on the Rooftop Deck or the Front Patio and definitely try one of the signature Frozen Cocktails.  Boystown is a place for everyone to feel welcome, accepted and to celebrate the best of Chicago nightlife.

One more thing

My visit to Boystown left me feeling in awe of the LGBTQ community and the neighborhood built against all odds. The struggle for equality has changed, but the people who make up Boystown continue to evolve, adapt, persevere and advocate for those who need it the most.

I always knew how special the neighborhood was, but I didn’t realize JUST how special. I didn’t know that it is one of the most unique, highly concentrated and comprehensive LGBTQ neighborhoods in the country and possibly the world. It was great to take pause, reflect and talk with the members of the community that helped establish Boystown and ensure that it remains a beacon to those who feel they don’t belong. Next time I head there for a fun evening out, I’ll be sure to take a moment and imagine what it’s like for an LGBTQ person seeing it for the first time.

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