Windy Chicago was the oldest queen in the area. She was a permanent fixture on a barstool at Mary's for many years. After performing for multiple decades, she went into retirement. She came out of a decade of retirement to perform at the GCAM show in 1999. She was wiry and thin, with an iconically tall hairdo and makeup.
In 2004, Walt Zipprian and Mark Johnson created a 20 minute long documentary about Wendy Chicago that premiered at a local theater in Houston. Wendy Chicago attended and performed, and GCAM mounted a drag exhibit.