Keith Howland started playing the guitar at the age of seven, and he played in a number of bands during his school years. He attended high 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. He also continued playing as much as possible, including a 1993 summer tour with Rick Springfield.
In 1995, Chicago was looking for a new lead guitarist to replace the departing Dawayne Bailey. Howland was a long-time fan of the band and Terry Kath (their original guitarist), and he showed up uninvited to the auditions. Thanks to a chance meeting with Jason Scheff (the band's bassist), Howland got a last-minute audition and was offered a job the same day.
Howland has also pursued projects outside the band, including outside work that he has done with Chicago's drummer Tris Imboden. Their collaborative effort is known as The Howland/Imboden Project, and two CDs have been released. The sound can be described as all-instrumental, jazz/rock/fusion. One CD is a studio effort (The Howland/Imboden Project), and the other is a live recording (Live At The Baked Potato).
In November 2007 Keith released a CD titled KeCraig. This CD started as a jam session in November 2007 with his brother Craig.
His latest project is a collaboration with former Chicago keyboardist, guitarist, and vocalist Bill Champlin on Champlin's 2008 solo album "No Place Left to Fall".