Born in Milton Keynes, Chilwell started his career at Leicester City, first joining the Foxes at the age of 12 before developing his game through the different age groups.
Chilwell won the Foxes' Academy Player of the Year award for the 2014/15 season and his first-team debut would follow only a few months later, in October against Hull City.
One month on, the attacking full-back was loaned to Championship club Huddersfield Town in a bid to gain first-team experience.