Cheap flights from Massachusetts to Portland from $106

The cheapest month to fly to Portland from Massachusetts is in May. Flight prices, which tend to average around $287, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in May, then you should wait until January to fly from Massachusetts, when ticket prices are also cheap, with an average price of $297.

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $353. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Portland is Sunday, with ticket prices averaging around $432.

The cheapest time of day to fly to Portland is in the afternoon when flights can be purchased for as low as $396. In the evening is when there is more demand to fly to Portland, so prices are often more expensive at around $480 per ticket.

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

You are more likely to see cheaper flights to Portland from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Massachusetts for as low as $305 on momondo.

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

Frontier, Alaska Airlines, and JetBlue are the most popular carriers operating from Massachusetts to Portland

Alaska Airlines, JetBlue and Hawaiian Airlines are the top three most popular airlines that fly to Portland from Massachusetts according to our data. Alaska Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 8 different airlines that fly to Portland on a routine basis, so you have a few additional options to choose from.

The number of flights available between Massachusetts and Portland is 1 per day as of March 2026. The most frequent departure time is 4:00PM, with 100% of daily flights leaving in the afternoon.

The number of flights available between Massachusetts and Portland is 10 per week as of March 2026. The most frequent departure day is Thu, with 30% of weekly flights leaving on this day.