Seeing as how well TOMI went down (appealing to old fans, and even introduced new people to the Monkey Island series) I think there's a good chance they will make another season. Tales seemed to be really successful from what I've heard, so continuing the series would probably be beneficial for both companies.
I wouldn't like to estimate when this will happen though. It may take a while, depending on what plans the other companies have for the near future (e.g. Telltale's next Sam and Max season) and they'd have to decide on where the storyline would go for a new Monkey Island season. But I think it's very likely there will be more Monkey Island someday!