Chad Winkler joined the Pittsburgh Symphony Orchestra as fourth/utility trumpet in November 2008 and has been featured as soloist with the Pittsburgh Symphony. Prior to winning the PSO position, Winkler held positions with the Wheeling Symphony, the West Virginia Symphony, and the Erie Philharmonic. He has appeared as guest principal trumpet with the orchestras of Indianapolis, Cincinnati, Detroit, and Rochester, and has performed with the Chicago Symphony Orchestra, as well as the orchestras of San Francisco, Houston, Minnesota, Honolulu, Louisville, and Jacksonville. He has served as acting principal trumpet with the orchestras of the Pittsburgh Ballet and Pittsburgh Opera, and is principal trumpet of the Lakeside Symphony Orchestra in Lakeside, Ohio.

Winkler has led masterclasses at the University of Michigan, Carnegie Mellon University, Duquesne University, Butler University, West Virginia University, and the Conservatory of Music in Puerto Rico, and has taught at the Masterworks Festival in Spartanburg, SC and the Eastman Trumpet Institute in Rochester, NY. At his home studio, the Pittsburgh South Hills Trumpet Studio, he teaches middle and high school students, some of whom have earned first-chair PMEA All-State placements and gone on to study music at Northwestern University, the Eastman School of Music, the Cleveland Institute of Music, Carnegie Mellon University, and the University of Michigan. In 2025, Winkler founded the Pittsburgh Trumpet Camp, a summer intensive that brings middle and high school trumpet players from across the region together for masterclasses, ensemble playing, and audition preparation, capped by a mass trumpet ensemble finale concert.

Winkler won the National Trumpet Competition in 1995, 1998, and 2000. In 2013, he was invited to perform as guest soloist at the National Trumpet Competition.

In 2020-21, Winkler began a SoundCloud project of recording standard trumpet repertoire, where he plays both the trumpet solo and piano accompaniment.

Originally from Morgantown, West Virginia, Winkler earned his Bachelor of Music degree from West Virginia University, where he studied with his father, Dr. John Winkler. Winkler earned his Master of Music degree from Duquesne University, where he studied with George Vosburgh, retired Pittsburgh Symphony principal trumpet.

Chad and his wife Elissa, who is Director of Music in Worship at Beverly Heights Church, live in Mt. Lebanon, Pennsylvania, with their son, Hudson, and daughter, Selah.