Cheap flights from Calgary to Boston from $169

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 $248. 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 $302.

The cheapest day to depart from Calgary to Boston is on a Sunday when prices can be found for as low as $281. 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 $246. 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 $349 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 $406 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 3 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.

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

WestJet, Air Canada and Delta 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 39% 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: 60% 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: 6h 47m.

Toronto (YYZ) has the shortest average layover time for this route: 1h 31m.

The number of flights available between Calgary and Boston is 4 per day as of August 2026. The most frequent departure time is 10:00AM, with 80% of daily flights leaving at noon.

34 flights are operational weekly from Calgary to Boston as of August 2026. The most popular departure day for this route is Fri, with 24% of flights per week taking off on this day.