Chamberlain's father, ex- Pompey and England winger Mark, recently said he would like his son to join Walcott at Arsenal.
Saints, though, are hoping to hang on to the exciting winger this summer, as they return to the Championship next season.
Surman told the Daily Echo: "It's not an easy decision for him to make.
"You've got massive clubs interested in you, and sometimes it's a dream to move to one of them. But, as a young player, you need to be playing week in and week out.
"Obviously, if you move to one of those top clubs then you are at a much higher standard of football. But will you be playing week in and week out?
"It's difficult to turn down clubs of that size if they come in for you, though.
"So it looks like he has got a bit of a decision to make."