Helliwell, 19, has been with Barnsley since he was 10 years old, joining The Tykes in April 2012. He made his first-team debut in November 2018, coming off the bench in a 2-1 win against Bradford City in the Checkatrade Trophy
He was named Barnsley’s 2017/18 Academy Player of the Year and has been a regular for their Under-23s team.
On his move, he said: “I’m really looking forward to the experience and challenge of playing competitive football at a good level.
"It’s important for my development that I have exposure first team football and I feel that Stalybridge offers me the perfect platform to go and play.
“I hope I can impress while on loan and see if I can push on more when I return to Barnsley.”