Chester was born and raised in Nelson where he began his career as a police officer. His role soon saw him relocate to Wellington, Auckland and even Patea.
In 2002 Chester graduated from Victoria University of Wellington with a Bachelor of Laws and was admitted to the bar before working as a lawyer in Hawera.
Chester was elected MP for Whanganui in 2005 and in 2014 became deputy speaker of the house.
In 2017 Chester decided he would not stand for re-election.
Chester and his wife Ella live in Hawera and have three children.