Sapphic Serenade: Dorothy's Karaoke Night hosted by E.
Don't miss the best queer karaoke night in town hosted by Dorothy's own bartender, E, featuring MONDAY MUSICALS POWER HOUR!
Queer Fiber Artist Night at Dorothy
Bring your fiber work to Dorothy and join in a community of artists gathering at their favorite lesbian bar!
Buffy the Vampire Slayer: Once More, with Feeling Sing-a-Long!
Join us while we stream the musical episode of Buffy as a community sing-a-long event this January.
Emo Night: All the Classics, All the Hits
Don't miss our first Emo Night of 2026 where we play all the classics and hits you love while raising money for the Chicago Food Depository.
The Bi Wives Club: A Comedy Showcase
The Bi Wives Club is back on February 1st with a stacked lineup of Chicago comedy stars! Not bi? No problem. Nobody's wife? Even better.
Chicago Party Clowns Present: My Funny Valentine
This Valentine’s season, the Chicago Party Clowns invite you to a glittery, giggle-packed night honoring all kinds of love.
DJ Feature: Hillery Banks at Dorothy
Hillery Banks brings eclectic, high-energy sound to Dorothy on February 6th! Come on out for her debut and dance the night away.
Dorothy's Silent Book Club!
Silent Book Club is a global community of readers and introverts, gathering together to read in quiet camaraderie. Read with us at Dorothy!
IRL: Heated Rivalry Singles Mixer!
Glendalough Distilleries presents the hottest singles mixer in town! Guests choose Shane or Ilya and do their best to match. Let's play. :)
Playback in Love: Based on Your True Love Stories
Playback Theatre brings an interactive form of improvisational theatre centered around stories from the audience.
Venusian Visions: a monthly pop up tarot event at Dorothy
Venus pops up with us offering tarot readings blending mediumship and spell work at Dorothy from 6-10pm.
Erotic Storytelling with Smutty Black Gxrl
After a smash debut event with us this October, Smutty Black Gxrl is back with another night of sensuality, sexuality & erotic performance.
DJ Feature: Ca$h Era at Dorothy
Catch our 2026 Resident DJ Ca$h EraChicago popping up on the 2nd Friday of every month right here at Dorothy!
SHE LOVES ME / NOT - Dorothy's Valentines Night
Don Julio presents the party of night right here at Dorothy - a celebration of lovers, haters and everyone in between.
Off the Page: a Night of Queer Comix Readings
Join us for Off the Page's return as five cartoonists come together to share their work off the page and into live reading performances!
Queer Movie Monday: BESSIE
Join us for a screening of the 2015 HBO film BESSIE starring Queen Latifah as Bessie Smith in the first of our Queer Movie Mondays!
Queering Chaos Conversations: Queering Dreaming & Dreams
In the final of the panelist driven conversations led by Dr. Nicole Rawls, queer folks gather to connect & share in these chaotic times.
Tromblau&Friends Presents: Because We Love You
Don't miss this post-Valentine's week event with some of Chicago's top tier jazz talent coming together to share love songs with you.
Pisces Night ft. Astrology Readings by Toby Everhart
Calling all Pisces and those who love them! Come celebrate your season with a custom cocktail & astrology reading options by Toby.
Sapphic Serenade: Friday Night Feelings
Our queer karaoke night is getting a bonus weekend feature! The third Friday of every month will blast off with queer karaoke hosted by E!
DJ Feature: TMD at Dorothy
TMD brings old school rave energy to Dorothy on February 21st! Come on out for her debut and dance the night away.
Eldest Daughter 4 Eldest Daughter: Music Night & Mixer
Come meet and mingle with fellow eldest daughters and those who identify with that ambitious, care-centered, big love ethos we all crave.
Buffy the Vampire Slayer: Once More, with Feeling Sing-a-Long!
Join us while we stream the musical episode of Buffy as a community sing-a-long event this January.