How do character upgrades interact with Dispatcher's special ability?
Yes, this is a legal move, and it is clarified in the rules (page 5) (emphasis mine):


  When the Dispatcher moves a player’s pawn as if it were his own:
  
  • use the Dispatcher’s scars and upgrades, not those belonging to the
  character he is moving,
  
  • cards that need to be played or discarded (for Direct and Charter Flights
  or to enter a collapsing or fallen city) come from the Dispatcher’s hand.
  A card discarded for a Charter Flight must match the city the pawn is
  moving from.


The Pilot upgrade allows your character to take a Direct Flight without discarding the card. I don't see an upgrade that allows you to take a Charter Flight without discarding, however, so be sure you're using the correct action. Looking around on google, a Pilot Dispatcher is a very common combination, as it is very efficient to move players around that way.