I'd suggest goin by car, but if u go by plane, u'll have to hire a car or go by bus to Iraq, there's no other way and you cannot go there alone. Secondly, if you go to iraq from syria or jordan u need a multiple entry visa to get back in syria or jordan. I suggest going to Jordan by cab aswell from syria or even the other way round, it will save you alot of money. You need to get intouch with the embessies for more details and info.

By the way try applying two week prior to your travel. They usually take along time for Canadian, European, American, south African and Austrailian passports.

It's always the small things that make big differences.