Cheap flights from Boston to Portland from $144

The cheapest month to fly to Portland from Boston is in January. Flight prices, which tend to average around $297, are often lower during this time because this is during the off-season. If you don’t want to visit Portland in January, then you should wait until May to fly from Boston, when ticket prices are also cheap, with an average price of $327.

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $384. 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 $471.

The cheapest time of day to fly to Portland is in the afternoon when flights can be purchased for as low as $414. In the evening is when there is more demand to fly to Portland, so prices are often more expensive at around $437 per ticket.

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

You are more likely to see cheaper flights to Portland from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland for around $380 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland from Boston for as low as $313 on momondo.

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

As of May 2026, prices for Boston to Portland flights are approximately 27% cheaper when compared to flights at the same time last year.

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

Alaska Airlines, JetBlue and Delta are the top three most popular airlines that fly to Portland from Boston 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 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.

Chicago (ORD) was the most common stop: 25% of momondo users choosing 1-stop flights on this route connected there.

Flights via Charlotte (CLT) offer the lowest average round-trip price of $193.

Flights connecting via Salt Lake City (SLC) have the shortest average one-way travel time: 7h 53m.

Salt Lake City (SLC) has the shortest average layover time for this route: 0h 47m.