In order john wake up in the morning headed to the plane, he must need to fly up to the plane into it. so how can he do that?

this doesn't make any since but I will finish your made up story.

Explanation:

How he did that was he was sleep walking and BOOM! when he got onto the plane he was awake and super confused and so he walked of off the plane back into dream land. :)

Thomas might have been using both meanings in the poem so that he can show how kind he is.