Chicago Roundup

TODAY IS THE DAY! Tonight at 7:00 PM, the ultimate q***r, sober prom do-over begins! 🪩✨

We are throwing it back to the exact decade the Chicago Roundup was born for an unforgettable night of high-energy music, deep connection, and unapologetic celebration. Professional prom pics, epic nostalgic tracks, and two shimmering prom royalty crowns are waiting for you.

Doors open at 7:00 PM at Holy Covenant United Methodist Church (925 W Diversey Pkwy). Bring your brightest, most authentic self, your chosen family, and your most fabulous '80s looks. Online ticket sales are live right now—grab yours at chicagoroundup.org/prom and we'll see you on the dance floor!

Dress the theme or come as you are; pay what you can — this event is for everyone.

Let’s make some permanent memories, darlings! We will have a professional photographer on-site this Friday night to capture classic, hilariously nostalgic, high-glam prom pictures of you and your entire crew! 📸✨

This night is a glittering, joyful bridge across generations—a chance to hit the dance floor surrounded by pure community, celebrating how far we’ve come and creating epic new memories with the family we chose along the way. You are going to want to preserve these looks forever, so dust off the shoulder pads and get ready for your close-up.

Tomorrow is the night! Online ticket sales are burning up, so make sure you lock yours in before we hit the dance floor. Grab them now at chicagoroundup.org/prom

Come as you are—or pop off with your look! 💖 No matter where you are in your journey, how you express your gender, or what your recovery looks like, there is a prominent, glittering spot for you on our dance floor this Friday night.

Whether your vibe is rolling up in a comfortable t-shirt and jeans, or serving full-blown vintage glamour with giant hair and exploding sequins, you belong here. No pressure, no dress code policing, and absolutely no editing yourself.

For those who lived through the era, this is your chance to rewrite a night that may have happened before you were out, before you found your chosen family, or before you found the joy of sobriety. For our younger generations, it’s a direct invitation to step into a legendary time capsule and experience the vibrant, electric energy of an iconic decade.

Just pure community, nostalgic hits, and unapologetic celebration. Sn**ch your tickets at chicagoroundup.org/prom

Did someone say royalty?! 👑👑 This Friday night, we aren't holding back—we are crowning TWO members of our community as Prom Royalty!

The category is '80s Prom Royalty, which means we want to see you turning look after look. Give us your biggest hair, your brightest neon, your boldest sequins, and your wildest ruffles. Whether you go full vintage glamour or put a modern, extra-flamboyant twist on the decade, dress to express your truest self.

Who will take home the crowns? Find out this Friday, June 12th at Holy Covenant United Methodist Church. Doors open at 7:00 PM. Secure your spot on the dance floor right now at chicagoroundup.org/prom

Pride season is officially here, and honey, it can be a lot! It’s beautiful and celebratory, but it can also feel substance-heavy. If you’re looking for a grounded, gorgeous space to celebrate exactly who you are, let this Friday night be your anchor. ⚓✨

Join us on Friday, June 12th at 7:00 PM for the most unforgettable, over-the-top '80s Prom Chicago has (probably) ever seen! We are turning back the clock to reclaim a classic milestone through a fiercely q***r, sober lens—giving our community the ultimate do-over to experience prom exactly as our brightest, most flamboyant, authentic selves.

Come solo, bring a hot date, or assemble your entire chosen family. Let’s kick off Pride Month centered in pure community, connection, and maximum joy. Tickets and full details are waiting for you at chicagoroundup.org/prom

The Chicago Roundup is looking for contestants to take the stage for the storied Serenity Pageant on Saturday, September 5th at the Greenhouse Theater Center. This legendary tradition celebrates the brilliant intersection of drag artistry and sober joy, and we want you to step into the spotlight.

The competition is open to performers across the entire spectrum of gender and recovery fellowships. Whether you have a breathtaking talent to showcase, an unforgettable evening attire look to debut, or a story of resilience to share, this is your moment to shine and celebrate the vibrant creative expression found in our community. Contestants will compete to determine who will be crowned the next Mr., Mx., or Miss Serenity.

If you or someone you know has a performance in their heart and a desire to honor our collective journey of recovery, we want to hear from you. Reach out to our pageant coordinators today to learn more or to enter the running:

Andy F: [email protected]
Melissa Y: [email protected]

Dust off the shoulder pads, tease the hair to the heavens, and get ready to rule the school!

On Friday, June 12th at 7:00 PM, we are throwing it back to the exact decade the Chicago Roundup was born for an unforgettable '80s Prom. This Pride Month, we are turning back the clock to reclaim a classic milestone through a fiercely q***r, sober lens—giving our community the ultimate do-over to experience prom exactly as our brightest, most authentic selves.

For those who lived through the era, it’s a chance to rewrite a night that may have happened before you were out, before you found your chosen family, or before you found the joy of sobriety. And for younger generations, it’s an invitation to step into a legendary time capsule and experience the vibrant energy of an era you’ve only heard stories about. This night is a glittering, joyful bridge across generations—a chance to hit the dance floor surrounded by pure community, celebrating how far we’ve come and creating epic new memories with the family we chose along the way.

Grab a date, assemble the chosen family, or come solo and find your crowd on the dance floor. Expect a night of high-energy music, nostalgic hits, and unapologetic celebration. The look is '80s Prom Royalty, so big hair, neon, sequins, and ruffles are highly encouraged.

Tickets and full details are available at chicagoroundup.org/prom

All paths lead to the 40th Anniversary Chicago Roundup.

Whether you are traveling across the country or just across the state, getting to our November homecoming is easy.

By Air: Chicago is one of the most accessible cities in the world. O’Hare (ORD) and Midway (MDW) both offer direct flights from almost every major city. Once you land, the "L" trains provide a direct, low-cost connection straight into the heart of downtown.

By Rail: For those who prefer the scenic route, Amtrak arrives at Union Station, just a short ride from the voco and Holiday Inn. It’s a great way to start the "We Keep Coming Back" weekend by connecting with others on the journey.

Plan your travel early to secure the best rates and maximize your time with the fellowship.

🔗 Travel details & registration: chicagoroundup.org/travel

Make your stay part of the fellowship.

One of the best ways to experience the "We Keep Coming Back" Roundup is by staying exactly where the action happens. By booking within our hotel block, you stay connected to the community from the first morning workshop to the late-night hospitality lounge.

Our premier host venue, voco Chicago Downtown, offers a sophisticated sanctuary right on the Chicago River. Enjoy refined amenities, the 14th-floor foyer for receptions, and the elegant Sauganash Ballroom for our main events.

For a more budget-friendly option, our sister hotel—the Holiday Inn Chicago Downtown - the Mart—is located in the same building. You get the same convenient access to every session and social hour without ever having to leave the complex.

Special Roundup room rates are available through October 14.

🔗 Book your room: chicagoroundup.org/hotels