Cheap flights from Calgary to Boston from $171

In general, October is the cheapest month to fly from Calgary to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $263. If you aren’t able to travel during the month of October, then book flights to Boston from Calgary during September instead. Flights to Boston in September, while not as cheap as those in October, still average around $284.

The cheapest day to depart from Calgary to Boston is on a Friday when prices can be found for as low as $241. Be sure to avoid booking your departure on a Monday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Monday is $957.

According to our data, the cheapest time of day to fly to Boston is in the afternoon. momondo users have found flights departing from Calgary to Boston in the afternoon for as low as $294. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In the morning is when there is more demand to fly to Boston, so prices are often more expensive at around $378 per ticket.

Fly from Calgary to Boston Logan Intl for the best Calgary - Boston Logan Intl flight prices

You are more likely to see cheaper flights to Boston from Calgary when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $426 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Calgary for as low as $194 on momondo.

There are 2 cabin classes available to choose from on Calgary to Boston flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Calgary to Boston.

As of November 2026, prices for Calgary to Boston flights are approximately 20% cheaper when compared to flights at the same time last year.

Porter Airlines and United Airlines are the most popular carriers operating from Calgary to Boston Logan Intl

WestJet, Air Canada and Porter Airlines are the top three most popular airlines that fly to Boston from Calgary according to our data. WestJet is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 4 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Ottawa (YOW) was the most common stop: 50% of momondo users choosing 1-stop flights on this route connected there.

Flights via Ottawa (YOW) offer the lowest average round-trip price of $466.

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 7h 11m.

Toronto (YYZ) has the shortest average layover time for this route: 1h 47m.