Chicago Transgender Videos

Browse our selection of Chicago transgender videos. Entertainment, educational and newsmakers in the Chicago trans scene. Click any of the videos to play right here on the Chicago-Transgender.com website.

Five of Chicago’s Fiercest Drag Queens

The best drag queens that Chicago has to offer. Every entertainer has their own style, energy, and fanbase that make them Chitown’s favorites to follow.


Out In Chicago: Trans Activism

Documentary: Listen to what these contemporary trans Chicagoans have to say about civic responsibility and the rights most people take for granted.


Love and Hip Hop of Chicago

Transgender Diva Sidney Starr’s Audition Video for Love3 and Hip Hop of Chicago


Schoolboy to Showgirl: The Alexandra Billings Story

A 30 second promo for a WTTW documentary in the Out & Proud in Chicago series, SCHOOLBOY TO SHOWGIRL: THE ALEXANDRA BILLINGS STORY.


The Vixen SAIC Drag Show

The vixen performing at School of Art institute Chicago.


Chicago’s Transgender Community – a tale of two communities

A news report by Dave Keating of WTTW PBS.


Trans Teen Cheerleader Prepares to Face the World

A Chicago trans high school cheerleader discovers he’s not gay but trans, and with the help and support of her family, teachers and teammates, begins her transition all the while cheering her team onto victory.


Trans teen in Chicago: from surviving to thriving

Bathroom battles are quickly evolving into a key issue in the American culture wars while families and their transgender children try to obtain safe access to restrooms at school.


Episcopal Priest in Chicago: Let’s Make Everyone Welcome – Including Transgender People

Emily Guffey Williams is an associate rector at All Saints and has been serving there for two years, following her time in Seminary.


Chicago Pride Parade 2017

Chicago Pride: Lesbian, gay, bisexual and transgender. ALL WELCOME…Gay Pride Parade in Chicago