Scott’s Cheap Flights is listing deals from a ton of cities in the US and Canada to Hawaii. While not all of the prices are hot, the breadth of the sale means there are many cities that don’t often see sales with good prices to Hawaii. Furthermore, departures from Canada can be a great deal, with round trip flights from Montreal and Toronto ringing in around $456.
The sales are good to Maui (OGG), Kona (KOA), and Honolulu (HNL). Many of the flights listed below may be even cheaper if you book through OTAs at meta-search site Momondo. For ease of compilation and modification of dates and cities, results from Google Flights are shown. If you find a set of dates with a price you like, put the same cities and dates in at Momondo.com and you may be able to save a few bucks (though YMMV with regard to reliability of the OTAs there).
Some examples follow (click the images to go to Google Flights), but subscribe to Scott’s Cheap Flights for more info.
Toronto to Honolulu from $456 (similar price to Kona or Maui)
There are some solid prices to the Hawaiian islands available. There are decent prices from many more cities — it’s worth putting in your preferred cities at dates at Google Flights to see what’s available. Many of these prices are available between now and May 2018, but YMMV based on city pairs. For those who have signed up for an Alaska Airlines Visa Signature card with a free companion fare, deals on Alaska may be particularly attractive. You may be able to open jaw with a return from a different island — I certainly recommend trying to see at least two islands if you have the time. If you find any other notable deals, feel free to add them in the comments.