My 50-ish lb dog has flown both domestic and international. I taught her about crates when she was 8wk old but I think if you are crate training him now, he will find comfort in his crate.

Westjet is AWESOME with pets!!!! Can't say enough good things. I've flown with a cat in cabin and dog in luggage. They have a very good system and are very reassuring they will take good care.

You are welcome to come visit me!! Waterloo has an airport. And a train station!