He attended elementary school in Richmond, Virginia, and graduated from James Madison University in 1986 with a degree in communications.

In 1987, Keith moved to Los Angeles and took a job with Andy Brauer Studio Rentals, which helped him to make invaluable contacts in the music industry.

Howland appeared uninvited at the auditions, and attained a chance meeting with the band's bassist, Jason Scheff.

[1] On November 15, 2021, Howland suffered a broken arm in an accident and took a leave of absence from the band.

[2] On December 1, 2021, Howland announced his resignation from Chicago after more than 26 years, citing lengthy recovery time before being able to resume playing guitar, and the desire to begin the next phase of his life.