Cheap flights from Portland to Massachusetts from $128

In general, January is the cheapest month to fly from Portland to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $327. If you aren’t able to travel to Massachusetts during the month of January, then flying in May is also cheap. Prices for this month can be found on momondo for an average of $352.

According to our data, Friday is the cheapest day to fly to Massachusetts from Portland. The lowest ticket price found for a Friday departure recently was $427. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Portland because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $542.

Our data shows that the cheapest Portland to Massachusetts flights are usually those with departure times at noon. Our users have found flights to Massachusetts at noon for as low as $369. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $530 on average. Flights to Massachusetts from Portland in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

You are more likely to see cheaper flights to Massachusetts from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $405 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Portland for as low as $310 on momondo.

There are 4 cabin classes available to choose from on Portland to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

United Airlines, Southwest, and Delta are the most popular carriers operating from Portland to Massachusetts

Alaska Airlines, JetBlue and Delta are the top three most popular airlines that fly to Massachusetts from Portland according to our data. Alaska Airlines is the first choice among our users, with 47% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 7 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

As of August 2026, there are 3 flights per day flying from Portland to Massachusetts. The most common time of day flights depart is 11:00PM, with 59% of flights taking off in the evening.

The number of flights available between Portland and Massachusetts is 27 per week as of August 2026. The most frequent departure day is Fri, with 30% of weekly flights leaving on this day.