I think it's important to understand exactly what your options are when looking for an all inclusive package. It may seem like there's an overwhelming variety of places to search and scour, but in reality there's really only 2 worlds of prices available to us Canadians.
Solution #1 - The Canadian Tour Operators (Sunwing, Transat Holidays, Nolitours, WestjetVacations, etc)
Solution #2 - Everything Else (packages from Expedia, Travelocity, Orbitz, Bookit, Voyages Aqua Terra, etc)
It never hurts to check both worlds, just be sure you're comparing apples to apples, in terms of what you're getting.
4-5 weeks ahead is usually a good time for decent overall prices from the CTO's, just don't expect anything decent over Christmas or around the third week of February.
Watch for the crazy sell-offs from the CTO's with under a week to go, but be open to anything, anywhere.