Cheap flights from Boston to Portland from $189

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 February to fly from Boston, when ticket prices are also cheap, with an average price of $367.

The cheapest day to depart on your flight to Portland is on a Wednesday when prices can be found for as low as $425. 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 $484.

The cheapest time of day to fly to Portland is in the evening when flights can be purchased for as low as $396. In the afternoon 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 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 $414 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 $358 on momondo.

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

Alaska Airlines, United Airlines, 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 42% of people opting to fly with this airline when traveling to Portland. Keep in mind that there are 6 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: 42% 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 Seattle (SEA) have the shortest average one-way travel time: 8h 18m.

Chicago (ORD) has the shortest average layover time for this route: 1h 14m.

The number of flights available between Boston and Portland is 1 per day as of October 2026. The most frequent departure time is 10:00AM, with 75% of daily flights leaving at noon.

As of October 2026, there are 13 flights per week flying from Boston to Portland. The most common day of the week flights depart is Mon, with 23% of flights taking off on this day.