Chicago Roundup

09/29/2026

For four decades, the Chicago Roundup has been a home for our community. As we prepare for our 40th Anniversary, we are building a history project to honor the generations of recovery that built this event, and we need your photos to bring it to life!

If you have photos from past Roundups, please email them to [email protected].

All submitted photos will be displayed exclusively on-site during the Roundup weekend for members of our recovery community. Nothing will be posted publicly online or shared outside event spaces to ensure everyone's anonymity is protected.

Dig through your physical albums and camera rolls, and send your favorite memories to Melissa today!

09/22/2026

Scholarship applications for the 40th Anniversary Chicago Roundup are now open!

The first priority review deadline is October 5th, with final applications closing October 26th.

Apply for full or partial assistance at chicagoroundup.org/scholarship

09/18/2026

The Chicago Roundup is grateful for the support of No Matter What Recovery.

No Matter What Recovery is a dual diagnosis treatment provider and a lifeline to wellness for individuals seeking affirming, trauma-informed care across every stage of recovery.

Their team is deeply committed to providing LGBTQ+ affirming treatment while unraveling the complexities of chemsex and sexualized drug use, exploring the impact of family systems, and honoring the transgender experience in recovery. They serve both LGBTQ+ clients and true allies who value culturally competent, clinically-grounded care.

No Matter What Recovery offers outpatient care in the heart of Chicago’s Boystown, near the intersection of Halsted and Belmont.

nomatterwhatrecovery.com/locations/chicago

09/15/2026

Is your sponsor telling you to get a service commitment? Help out by volunteering for the Chicago Roundup at

Volunteer signup sheet

09/07/2026

Help spread the word!

Make these announcements in your meetings:

Meeting Anouncements This page is updated regularly with current Chicago Roundup news to share during the announcements portion of your recovery meetings.Thank you for taking a moment to share this information with your meetings — it helps keep our community connected and informed!Please bookmark ...

09/06/2026

Post-Serenity 🚨FLASH SALE🚨 for the Chicago Roundup:

Take $50 off event registration now through the end of Sunday with promo code SERENITYFLASHSALE!

Lock in the lowest rate offered for the event!

(Includes Mrs. Kasha Davis performance.)

By Chicago Roundup

09/06/2026

Just announced!

Mrs. Kasha Davis headlines November's Chicago Roundup!

Admission is included in Roundup registration,
or $40 for the public as a stand-alone ticket!

Join us Saturday night at the Chicago Roundup Conference

09/04/2026

Hey everybody, it’s Melissa@ from the Chicago Roundup letting you know we still have tickets available for the serenity pageant tomorrow at 7 PM!

The Serenity Pageant benefits the Serenity Scholarship which is so BIPOC and trans individuals can attend the Chicago Roundup, which is in November. It is a great cause and a great event.

Who doesn’t love a drag pageant?

Who will bring home the crown?

Hosted by Edna D Mascará, Fonda Coxx from New York, and Jackson Masters (who is that guy), with a performances by the House of Mascara!

We are almost sold out of VIP tickets, but we still have general admission tickets available.

If you click the little thing in the upper left-hand corner, you can change your ticket type. And you can still get general admission.

So come on out — we’ll see you tomorrow night at the Greenhouse Theater Center to benefit the Chicago Roundup and the Serenity Scholarship Fund!

chicagoroundup.org/serenity

08/31/2026

Hello my Chicago friends! I am so excited to be hosting the Mx. Serenity Pageant happening Saturday, September 5 in Chicago. get your tickets at chicagoroundup.org/serenity. I’ll be hosting with Edna D Mascara and Jackson Masters. I can’t wait to see you there!

08/27/2026

The stage is set! Meet your 2026 Serenity Pageant contestants:

✨ The Holland Tunnel
✨ Goldie Showers
✨ Fran
✨ Melani
✨ W***e of Babylon

Join hosts Edna D. Mascara & Fonda Coxx alongside Jackson Masters as these 5 performers vie for the crown of Mr., Mx., or Miss Serenity!

All genders. All glam. One crown. A storied tradition of LGBTQIA2+ sober joy.

Date: Saturday, September 5th
Time: 7:00 PM
Location: Greenhouse Theater Center (2257 N Lincoln Ave)
Tickets & Info: chicagoroundup.org/serenity

100% of proceeds directly support the Serenity Scholarship Fund & The Chicago Roundup. Don't wait—grab your tickets before they sell out!