Dorothy (2500 W Chicago Ave, Chicago), commonly referred to around Chicago as Dorothy Downstairs, is a sapphic safehouse fuelled by a sultry speakeasy aesthetic, exquisite cocktails and uniquely crafted entertainment geared toward the lesbian community and “every friend of Dorothy.” Located in the West Town neighbourhood, this lounge of lesbos, which opened on Valentine’s Day 2020, is a must-see for visitors seeking out Chicago’s hot and sexy queer spots.
Co-owner and creative director Whitney LaMora talked to Pink Ticket Travel about her experience as a bar owner and events producer dedicated to keeping lesbian bars not just alive but thriving and evolving.
Tell me about the origin story of Dorothy bar.
In 2017 I was working a corporate nine-to-five job, but I wanted to open my own events venue. I began renting spaces and producing events throughout the city, but I found that juggling experience to be less than ideal.
I ended up applying at Splitrail [which is, sadly, permanently closed], a Chicago restaurant owned and operated by, spoiler, my now wife, chef Zoe Schor. So I met my future wife during my job interview there, and she ended up hiring me. I started to share with her my visions of opening up a new space. We became closer through her eagerness to share business advice and her support in helping me to actualize the space that is now Dorothy.
It was still early days when Zoe started speaking to me about the empty bar on the lower level of Splitrail’s building. She took me downstairs to see the space, which was covered completely in rubble. The venue was stripped to nothing but dust, wires, a piano and a massive bar.
Zoe wanted to take over the barren space, so I began helping her and her former business partner, Michelle, brainstorm ideas and put together Pinterest boards. In February of 2020, Zoe and Michelle successfully opened the bar. At that time, it was just a neighbourhood cocktail lounge. It was owned by queer women, and we wanted to implement queer nights, but the space hadn’t transformed into a lesbian bar just yet.
The bar was only open for a month before COVID-19 hit, and then we went dark for two years. I had no job for nearly 16 months. When we finally reopened, I came to the team as part of the management.
Meanwhile, in 2020, the Lesbian Bar Project was formed. This incredible group of filmmakers partnered with Jägermeister and came out with this incredible project, bringing awareness to the diminishing number of lesbian bars across the nation. Zoe and I were really inspired by that movement. At the same time, I was running a gallery upstairs, and we were starting to host events again. One of our events, Fruit Salad, which is our monthly queer open mic night, was gaining popularity like crazy and in a way that we absolutely didn’t anticipate.
So Zoe and I decided that we wanted to reopen Dorothy Downstairs as a lesbian bar. The name Dorothy was always a nod to the queer community, in reference to being a friend of Dorothy, which was a code word back in the day, used to identify people and spaces as queer-friendly.
We had a queer community forming already, and everything that happened between 2020 and 2021 really empowered business owners to label themselves and have confidence in being queer first and women-owned. People really wanted to know what your business core values were, and they were seeking out businesses that said, “Hey, we’re women-owned, we’re queer, we’re lesbian, this is where you can find your place.” So we were deeply inspired by the Lesbian Bar Project and Fruit Salad when we ultimately decided to open Dorothy as a lesbian bar.
A lot of queer people are looking for activities and spaces beyond the typical disco bar or nightclub. Does Dorothy offer something different to Chicago’s WLW community?
Dorothy isn’t a typical lesbian bar. I’ve been working professionally in events for almost a decade now, and events are really the core of any bar. We never envisioned Dorothy as a space with plastic cups and neon signs. Not that there’s anything wrong with that aesthetic—because who doesn’t love to party in those spaces? But the space we were working with was already a really unique environment, and it called for a very different type of event.
I often see queer bars with a lot of repeating content. Every Monday is trivia night, every Tuesday is Karaoke night—and that’s awesome and will draw people in multiple days a week. But because I have this background in events, and this already-built community of unique people looking to do unique things, I set out to make not only the most unique lesbian bar in Chicago but also the most unique programming in a gay bar that’s maybe ever been.
That means we don’t have a ton of repeat programming, and you won’t see the same thing over and over again at Dorothy. We have a couple of monthly shows, one of them being Fruit Salad. A lot of success with that event comes from the open mic aspect and the opportunity for people to come up and perform at Dorothy when they might not have ever gotten to do that before. We have a monthly burlesque show that’s also a big hit, and we’ve recently started doing monthly karaoke.
Other than those few repeating programs, it’s important for Dorothy to keep space open for as many people as possible, to come in and bring their unique perspectives to the bar. That has been key to getting people to come in as often as we need them to come in to continue to be profitable.
Just because our space is beautiful, just because we have awesome cocktails and just because we are one of the few lesbian bars in the city, and certainly one of the few gay spaces on this side of town—that still doesn’t bring people out six nights a week. So we’re really dedicated to holding space for unique events and performances.
My wife and I are white, cis, lesbian women, so we need a lot of different voices to come in to make sure that different people are coming into our bar, which we built for the lesbian community and not just people who look like us. I try to bring in as much talent as I can, and we pay every single host, producer and artist that comes through as fairly as we can.
How do you scout such unique talent?
It’s a combination of different types of outreach. I’m very plugged in to Chicago and what’s going on here. I’ve pulled in people who have performed at our open mic and said, “Yo, come be a feature on this or that,” and I connect with them that way.
Some people will just shoot their shot by sending me an email or a DM, and I always want to be a space that is open to that. As long as it sounds like a good fit for us, I try to say yes as often as I can. Most of the time that works out great. We have had events that turned out to be terrible, but we learn from them and move on.
What inspired your speakeasy aesthetic?
We always joke that we’re a speakeasy, but we really want you to know where we are.
The vibe for Dorothy was always 1970s inspired. We describe it as a sexy, ’70s, subterranean lounge. The ’70s aesthetic—maroons and burnt oranges—started coming out in its early conception. We really wanted to focus on the concept of the ’70s conversation couches, which are these incredible, massive couches that are meant for you to just sit down and never get up from, and to have these beautiful, long conversations. That was the inspiration for our custom-built bed lounge, which you see when you first walk down the steps that lead into Dorothy.
Our local vintage shop in the neighbourhood called Vintage Quest (1105 N. California Ave., Chicago) had a Togo couch, which is a couch from the ’70s that sits right on the floor, and that turned out to be the best purchase that we could have made. It’s just like, “Sit, relax, don’t get up.”
How would you describe the mission of Dorothy to visitors and out-of-towners?
Our mission is to create a space for anyone that feels comfortable to come in and be their true, authentic selves. It is similar to the Lesbian Bar Project’s in that we strive to be a safe, queer space for people who identify as lesbian and whoever wants to claim that label. Our space extends to the entire LGBTQIA2S+ community, but it’s important to us to keep the lesbian bar alive, so that’s why we label Dorothy that way first.
We have incredible staff and security that are dedicated to keeping our space safe. We’ve had the same staff since we opened, which is unheard of in the service industry. We hire security because the unfortunate reality of being a queer bar in America, is that we could potentially be under attack.
We work really hard with our security team to make sure that from the moment folks come in, however they’re presenting themselves and whatever they’re coming in for, they feel welcome and like they’re entering a safe space where they’re not only physically protected but emotionally protected as well.
Just making a beautiful environment is also a part of our mission. That means having awesome cocktails on the menu, having beverages at every price point, having spirit-free options and never blinking an eye if someone asks for something that we don’t have. We offer a top-tier level of hospitality.
We want Dorothy to be a beautiful experience for everyone, but especially for people who need the space in a way that a lot of people, maybe straight people, don’t understand if they’ve never had to find and seek out spaces where they actually feel comfortable, and can be around other similarly presenting people.
Any advice for queer travellers?
I encourage any queer people to seek out what’s queer in the city they’re visiting. It takes queer businesses a lot of work to make sure that we’re hitting our numbers. Shopping small and supporting causes that are important to you while travelling makes a huge difference. If someone decides to have a drink in our bar versus at a chain or at one of the huge names in our city, it makes such a difference to us, and guarantees that we can continue to stick around.
Seek out the lesbian bars, talk to the bartenders, let them know that you’re there for the first time. Ask them where else to go, and especially if you’re a queer person who is nervous about travelling, talk to the people at lesbian bars and ask them where they go where they can feel safe.
Utilize these spaces and have conversations. The queer community is awesome, and we’re always looking out for each other. Be intentional with where you’re going, and if you’re reading a publication like this, you’re already doing that. Try to make that a practice, and it will make all the difference in keeping businesses like ours alive.
This interview has been edited for length and clarity.
