Courtney Vondran has been living in the Chicago area most of her life, but had to relearn the city through a queer lens when she came out at 29 years old in 2020. Vondran — who uses both she/they pronouns — didn’t know what bars to go to, which vacation spots are welcoming, or how to find a queer community in Chicago. This inspired them to start highlighting queer-friendly hotspots in Chicago and the U.S. on Instagram and TikTok. Vondran is now a full-time content creator, with more than 100,000 followers across the two platforms.

Vondran fell in love with travel and sharing their experiences after quitting their HR job at 22 years old and starting a travel blog. They worked odd jobs to save for travel, including at a bar in Wrigleyville and the Cheesecake Factory on Michigan Avenue. Her travel blog audience grew, and then “exploded” when she came out as a lesbian to her followers. 

As an expert in how to experience the city as a queer person, she shared some tips on how to navigate LGBTQ spaces — and celebrate the holidays — in Chicago. 

What is your relationship with Chicago as a queer person?

It really feels like home. I think at first I was really trying to escape it because I was like, “This is what I know. I need to get out.” And the more I travel, the more I really fall in love with the city. And then the pandemic pushed me to explore more parks, the suburbs. And then coming out queer and really rediscovering the city as a queer person completely changed my perspective. And then again, leaving and coming back, I was like, “Wow, Chicago is like one of the most queer-friendly cities in the world.” It’s so special.

What inspired you to make a LGBTQ+ Chicago map?

The company Atly approached me about making a map. And I was like, what’s really missing in Chicago and what I really wanted as a person was a gay map of Chicago. So let’s do this partnership based on queer businesses and also the AIDs garden, and random things that I had no idea about — for example, the gay library in Chicago (the Gerber/Hart Library & Archives), or the Leather Museum. I’ve been here forever, and I’m just discovering these queer hidden gems.

It was really exciting realizing that I was queer, but was also a bit isolating as a late-in-life lesbian. I’m like, “Where are all the lesbians in Chicago?” I know the strip of Boystown, but I didn’t know that there’s a flannel night at this one particular bar in Wicker Park (Flannel Fridays take place at various bars across the city). So I created the map, because a lot of those things are important: Where are all the meetups? How do I meet queer friends? 

Photo: Courtney Vondran

Why is it important to have content like this on social media? In Chicago?

A part of it feels like passing the torch. I think that Chicago has such an incredible history of amazing advocates and amazing queer people that for decades have been paving the way for queer people and creating resources for free for us. A part of this feels like I’m continuing it within digital media. How can I strengthen the queer community within Chicago and put it on things that I know, like TikTok and Instagram? How can I uplift in my own way using my strengths?

Any advice on celebrating the holidays in Chicago as a queer person?

What I love about Chicago is that there’s literally things to do every single day. I just made a gay things to do in Chicago: HO HO HOMO EDITION guide. So there’s one thing to do almost every single day that you can be around your people and feel celebrated and feel seen. The queer community is very open and you if don’t have some place to go, you could meet someone at an event and literally probably go to Christmas at their apartment

Obviously, everybody likes to go to the pop-ups but it’s very hetero culture. For example, one of Liz (their fiancé) and I’s first date was going to a holiday pop-up. We left after 45 minutes. You get stared at. 

So, I enjoy going to (Humboldt Park queer bar) Dorothy, which has its own Christmas bar. I think a part of me wants to say gay in every way and to make Christmas as gay as possible. It feels like taking back the power in a way and just like making all of these things gay, more representation. I think that goes back to queer history of us taking back things. We’re taking back the word queer. We’re taking back all of these holidays. We’re having chosen family. 

Vondran’s Top Recommendations for the Holidays