Pirlo has been plying his trade at Milan since 2001, and the Italian international admitted that he's tempted to look for a new challenge in the Premiership.
"I don’t know if I will continue with Milan. I've been here for many years and maybe it is time to change and start a new chapter of my career," the 30-year-old said.
"It is possible that I will go to work with Carlo Ancelotti in London. He is a great manager and I'd love to play for him again."
Former Milan coach Ancelotti has been recently revealed as Chelsea's new tactician.
Pirlo, who played over 200 games for Milan, won a host of trophies with the San Siro outfit including one Serie A, one Coppa Italia and two UEFA Champions League trophies.
The former Inter Milan schemer is currently taking part with Italy in the Confederations Cup in South Africa.