Chesney's musical talent and ability as a singer became apparent at an early age. A native of Cleveland, Tennessee, a small town near Southern Adventist University, he began study in piano with Marvin Robertson at SAU at age ten and later, voice lessons. This was the beginning of a close mentor-student relationship that continues today.

He attended Little Creek Academy, a self-supporting school with an extensive music program in Knoxville, Tennessee, where he studied voice with Clara and Sara Ann Goodge and conducting with Leland Straw.

After graduating from LCA in 1977, Chesney entered Southern Missionary College, now Southern Adventist University. Although he initially enrolled as an English major, he changed to music. Influential teachers during his time at SMC were Robertson, Don Runyon, Orlo Gilbert, and Judy Glass. He completed a B.Mus.Ed. in 1983.

That fall, Chesney started teaching at Mount Pisgah Academy, where he directed the choir, gave voice lessons, and taught Bible classes for the next six years.

In 1989, he enrolled at the Eastman School of Music, studying voice with Seth McCoy and conducting with Don Neun. After completing an M.Mus. at ESM in 1990, he continued study at Michigan State University, where he studied voice with Claritha Buggs and conducting with Charles Smith. While there, he accepted the minister of music position at Forest Lake. He completed a DMA at MSU in 1998.

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