I'm sorry but your situation doesn't make much sense.
Yes, Italian citizenship is based on the principle of Jus Sanguinis, which means no birthright citizenship. However, foreigners born in Italy who have lived in Italy for 3 years can apply for Italian citizenship. This doesn't come automatically. You need to apply for it.
If you have been living in Italy for your whole life as you claim, you should apply for Italian citizenship. I doubt Italy, being an EU member state with due process, will arbitrarily deny your citizenship application if you're eligible, and if for some reason they do I'm sure you will have recourse of some sort.
You have a residence permit until 2019, which means you're not "irregular."
Your odds in Canada, especially if you're eligible for Italian citizenship, is practically nill.
I suggest you contact an Italian immigration/citizenship lawyer to check your options.