Cheap flights from Portland to Boston from $138

In general, August is the cheapest month to fly from Portland to Boston. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $317. If you aren’t able to travel during the month of August, then book flights to Boston from Portland during January instead. Flights to Boston in January, while not as cheap as those in August, still average around $326.

The cheapest day to depart from Portland to Boston is on a Wednesday when prices can be found for as low as $398. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Boston on Sunday is $529.

According to our data, the cheapest time of day to fly to Boston is at noon. momondo users have found flights departing from Portland to Boston at noon for as low as $375. 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 $515 per ticket.

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

You are more likely to see cheaper flights to Boston from Portland when booking weeks ahead of your departure date. In general, you can expect to find flights to Boston for around $395 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Boston from Portland for as low as $298 on momondo.

There are 4 cabin classes available to choose from on Portland 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 Portland to Boston.

As of May 2026, prices for Portland to Boston flights are approximately 1% cheaper when compared to flights at the same time last year.

Southwest, United Airlines, and Delta are the most popular carriers operating from Portland to Boston Logan Intl

Alaska Airlines, JetBlue and Delta are the top three most popular airlines that fly to Boston from Portland according to our data. Alaska Airlines is the first choice among our users, with 45% of people opting to fly with this airline when traveling to Boston. Keep in mind that there are 7 different airlines that fly to Boston on a routine basis, so you have a few additional options to choose from.

Chicago (ORD) was the most common stop: 70% of momondo users choosing 1-stop flights on this route connected there.

Flights via Seattle (SEA) offer the lowest average round-trip price of $243.

Flights connecting via Chicago (MDW) have the shortest average one-way travel time: 7h 25m.

Seattle (SEA) has the shortest average layover time for this route: 0h 51m.

As of May 2026, 2 flights take off from Portland and land in Boston each day. The most common flight departure time for this route is 2:00PM, with 36% of daily flights taking off in the afternoon.

As of May 2026, 14 flights take off from Portland and land in Boston each week. The most common flight departure day for this route is Mon, with 21% of weekly flights taking off on this day.