I have one whiner (Rexy 3 1/2 mo) and one non-whiner (Rowdy 14 mo).
I would suggest, if possible, to get him a console car seat (if your car has a console) that way, he can be right beside you, up by your face in the car. Rowdy is not a whiner, but he wants to be right next to me with his head on my arm or shoulder, at times.
Having Jack right beside you in the car may help the whining. Also, if he can't see out of the car to see where he is, he may be scared and that may contribute to the whining so a booster car seat may solve the problem.
Something else that may help is to give him is favorite chew toy in the car so that he is occupied. I have a car full of the favorite chew toys.
He may be slightly car sick and that may be why he whines in the car.
Whining in the house is to get his way and I'm a softee so I have no advice about that.
