Hoping to fly Southwest Airlines to Hawaii this year? Here’s an update. The airline’s CEO, Gary Kelly, says their plans to fly to Hawaii are on track, but right now they’re not sure whether flights will begin end of this year or early next. The timing depends on FAA approval for operating long flights over water. What Kelly is confident in, is that they will at least start selling tickets to Hawaii this year with plans to start its Hawaii service with flights from California.