Woakes was born in March 1989 in Birmingham, and attended Barr Beacon Language College from 2000–2007. He began playing cricket when he was seven years old. He started out with Aston Manor Cricket Club. He then played three games in the 2006 Minor Counties Trophy for Herefordshire, and for Warwickshire's under-15, under-17, Academy and Second XI teams between 2004 and 2007. He obtained 10 GCSEs including A's in Health and Social, Childcare, Hospitality and Business.

Chris married his long term girlfriend Amie on 10 February 2017. They have a daughter named Laila Louise who was born on the 2nd of July 2018.

Woakes represented Warwickshire in one match during the 2006 season, during a West Indian tour of England. Woakes picked up three wickets in the match. He has since represented Warwickshire in the Second XI Championship.

He was a regular for the Warwickshire First XI in 2008. He took 42 wickets at an average of 20.57 over the course of the County Championship season, topping Warwickshire's bowling averages.

On 6 April 2009, Woakes was given a call up to the England Cricket squad for the World Twenty20 in June. Allan Donald tipped Woakes as a future England international cricketer.