Not sure about crossing the border, but traveling by plane in Canada with a drone in a hand bagage is no problem at all.
Just declare it when they ask for electronic device and they are almost septical that a drone can fit in a small bag !
One thing ...Transport Canada laws:
Not allowed to fly:
-Higher that 90 meters / 300 feets.
-Max distance 500 meters / 1,600 feets and be able to see it.
-No night flight. Not in clouds.
-Within 75 meters / 250 feets of building, vehicles, people, animal.
-Within 9 kilometers / 5.5 miles from airport heliport.
-And must have your name, adress, phone number.
Comming soon: A rope attached to it ...... just jokeing !!! (I hope !)
Find are $3000.00 each offence and can be criminal charge if puting life at risk !
I know .....it suck !