Nice fares to Hawaii from all over the US & Canada into March 2018

I just caught a post at Heels First Travel that highlighted an airfare sale first posted at Scott’s Cheap Flights with a list of great prices to Hawaii from all over the US and Canada for travel from September 2017 to March 2018 (excluding some dates around the major holidays). The standout fares to me were from Toronto and Montreal at $412-$450 (in US Dollars) round trip to HonoluluMaui, and The Big Island (Kona). In fact, these cheap fares are even available during the Van’s World Cup of Surfing (which tells me is the Super Bowl of Surfing).

Red sand beach in Maui – no surfing here

I’m going to highlight a selection with links to Google Flights, but you should really go to Scott’s Cheap Flights and check it out — he’s done a lot more legwork in listing prices for various city fares (this sale is from a lot of cities).

Black sand beach on the big island

The thing to know about these is that the absolute cheapest prices are bookable via small online travel agencies that you can find through meta-search site Momondo. I personally don’t have experience booking with these agencies. I’m not sure that I wouldn’t use them — I know that in the worst-case scenario, I can file a chargeback on my credit card if they don’t provide me with the ticket I paid for — but if you do book with them, recognize that you are dealing with a less-established entity. That probably won’t matter on a trip that goes smoothly — but when you run into a canceled/delayed flight or other irregular operations, it could become a challenge. I’m going to list prices both from Google Flights (which should be available both directly at airline websites and through most major OTAs like Expedia, Priceline, etc) and Momondo. Choose your own adventure when it comes to where to book.

Sea turtle seen while snorkeling near Two-step, on the Kona side of The Big Island

Some examples:

Toronto to Honolulu November 28-December 7th (During the Van’s World Cup of Surfing) – $428437 

Van's World Cup of Surfing Hawaii

Click the image to go to Google Flights

Click the link to go to Momondo

Montreal to Honolulu September 6-13, from $412 / $429

Click the image to go to Google Flights

Click the image to go to Momondo

Montreal to Maui for Valentine’s Day $423 / $417

Click the image to go to Google Flights

Click the image to go to Momondo

Skip the eclipse and spend a month in Maui for a month? (Just a few dollars more if you want to spend only a week. Great use of one of a free companion fare if you recently signed up for the Alaska Airlines credit card.

New York to Maui, August 21-September 19: $591 / $577

Click the image to go to Google Flights

Click the image to go to Momondo

Chicago to Maui, September 26-October 3: $564 / $548

Click the image to go to Google Flights

Click the image to go to Momondo


Bottom line

These are just a few examples — there are tons of other great prices from a variety of cities, and Scott’s Flight Deals has tons of examples. Whether you’re looking for a fall getaway, the height of surfing season, or a romantic Valentine’s Day surprise, there are plenty of deals. Don’t forget the Alaska companion fare code if you’ve signed up for an Alaska credit card.

About Nick Reyes

Nick Reyes is a (fairly) regular guy with an animalistic passion for maximizing the value of miles and money to travel the world in comfort and style. There is little in life that he loves more than finding a fantastic deal and helping you shop smarter & harder to achieve your travel dreams.

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Maui and the other islands are an awesome for hiking as well. And during those month, the whales are down in the area also, you can hear them singing while snorkeling or scuba diving. I wrote about some of the activities in a trip report at


I could be wrong… but definitely being nit picky… in case it may matter to you… I think the picture of the black sand beach is Maui’s road to Hana, rather than the big island.


Ha! I thought *the exact same thing*!