To Boston

Cheap Flights from Portland to Boston

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Portland

RatePunk searches hundreds of travel sites at once for deals on flights to Boston

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Portland to Boston

Explore current cheapest deals departing from Portland to Boston

Round trip

Sort by: Cheapest

September 2 - September 9

Cheapest

PDX - Boston

$323

$202

Round trip

September 15 - September 30

PDX - Boston

$301

$230

Round trip

August 28 - August 31

Best

PDX - Boston

$771

$237

Round trip

August 10 - August 18

Best

Earliest

PDX - Boston

$710

$237

Round trip

August 11 - August 18

Best

PDX - Boston

$728

$237

Round trip

August 13 - August 21

Best

PDX - Boston

$715

$237

Round trip

August 19 - August 26

Best

PDX - Boston

$743

$237

Round trip

August 21 - August 28

Best

PDX - Boston

$743

$237

Round trip

August 24 - August 31

Best

PDX - Boston

$743

$237

Round trip

September 18 - September 21

PDX - Boston

$343

$237

Round trip

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Route Intelligence — 486,190 Searches this Week

Insights for flights from Portland to Boston

Most itineraries for flights from Portland to Boston connect at least once, with only 26.5% of recent fares being non-stop. For connecting itineraries, the typical number of stopovers is 2. This means that while direct flights from Portland to Boston are available, you will most often find options that include at least one connection.

When looking for cheap flights from Portland to Boston, you'll find that fares typically range from $317–$660, with a median price of $477. Right now, current fares are above the typical level. About 17% of recent fares were classified as a good price, indicating that competitive deals are available if you track prices. New deals appear almost daily, making it easier to find suitable options.

If you're wondering when is the cheapest time to fly from Portland to Boston, the data shows that January is typically the most affordable month, with a median fare of $119. Following closely, April also offers competitive prices with a median of $194. February is another cost-effective option, showing a median fare of $269.

A typical journey from Portland to Boston takes about 16h 35m, including connections. This route covers a significant distance of 4072 km, classifying it as a long-haul flight. Given the long-haul nature and the prevalence of connecting itineraries, the total travel time reflects the need for stopovers on most journeys.

How much is a round trip from Portland to Boston

Regular price: $271 - $492

Prices for flights from Portland to Boston are currently below the regular range.

The regular price range for flights from Portland to Boston is typically between $271 and $492. The current lowest deal is $202 with Southwest Airlines, for travel from Sep 2-Sep 9.

now $202

Low $271

High $492

The cheapest time to fly from Portland to Boston

The cheapest month to fly from Portland to Boston is January, with a median price of $119. The most expensive month is March, with a median price of $645. Generally, prices are lower from January to November.

January

Cheapest

Flights from $119

March

Most Expensive

Flights from $645

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Portland to Boston

JetBlue Airways

Last-minute flights going from Portland to Boston

Fri, Jul 10

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

American Airlines

$352

$238

One-way

Sun, Aug 2

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

JetBlue Airways

$702

$319

One-way

Thu, Aug 6

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

JetBlue Airways

$718

$318

One-way

Sat, Aug 8

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

JetBlue Airways

$642

$299

One-way

Sat, Aug 8

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

JetBlue Airways

$718

$328

One-way

Sun, Aug 9

⌛ Last-Minute

PDX - Boston

Portland (PDX) - Boston (BOS)

United Airlines

$708

$335

One-way

Biggest price drops on these dates for flights from Portland to Boston

3 nights

Aug 28 - Aug 31

$771 → $237

69%

2 nights

Aug 17 - Aug 19

$779 → $255

67%

5 nights

Aug 13 - Aug 18

$758 → $248

67%

3 nights

Aug 17 - Aug 20

$774 → $264

66%

Popular Airports to fly from Portland to Boston

Portland - Boston route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Portland to Boston are above the typical level, with a median price of $477.

📅 Best time to fly

January is historically the cheapest month to fly

Historically, January is the cheapest month to fly from Portland to Boston, with a median price of $119.

⏱️ Flight duration

Flights typically take 16h 35m

The median flight duration from Portland to Boston is 16 hours and 35 minutes, including layovers.

✈️ Airlines & availability

Connecting flights are dominant

Only 26.5% of deals are direct. Connecting flights typically involve 2 stopovers.

🏆 Airline highlight

Southwest Airlines offers a recent deal at $202

A recent deal from Portland to Boston was found on Southwest Airlines for $202.

🎯 Booking tip

Deals are frequent for this route

This route typically sees more than one deal per day, offering frequent opportunities to book.

Portland main airports to depart from

Portland International (PDX)

Cheapest

Portland International Airport is a convenient departure point for flights from Portland to Boston.

📍 ~10 km from Portland (reachable by car)

💸 Flights from ~$202

Boston main airports to arrive at

Logan International (BOS)

Cheapest

Logan International Airport is a primary gateway to Boston, offering convenient access for travelers from Portland.

📍 ~5 km from Boston city center (reachable by car, bus, subway, ferry)

💸 Flights from ~$202

Airports nearby Boston used as alternative

Rhode Island T. F. Green Int'l Airport (PVD)

Rhode Island T. F. Green Int'l Airport is a major regional alternative with a wide range of connections.

📍 ~46 km from Boston (approximately 1 hour drive from downtown Boston depending on traffic)

💸 Flights from ~$326

Manchester–Boston Regional (MHT)

Manchester–Boston Regional is a primary alternative for travelers north of Boston, with strong domestic network.

📍 ~73 km from Boston

💸 Flights from ~$355

Bradley International (BDL)

Bradley International is a large international airport, a reliable alternative for long-haul domestic flights.

📍 ~142 km from Boston (requiring a nearly 2-hour drive)

💸 Flights from ~$355

Portland International Jetport (PWM)

Portland International Jetport is a highly reliable regional jetport with good connectivity for northern suburbs.

📍 ~155 km from Boston

💸 Flights from ~$333

Worcester Regional (ORH)

Cheapest

Worcester Regional is geographically close to western Boston suburbs and offers a low-stress environment.

📍 ~68 km from Boston

💸 Flights from ~$213

Business & First Class Flight Deals to Boston

68% AI deal score

$2,735

From PDX

Elite

Jun 18

Boston, United States

68% AI deal score

$2,738

From PDX

Elite

Jun 18

Boston, United States

67% AI deal score

$2,681

From PDX

Elite

Jun 18

Boston, United States

67% AI deal score

$2,683

Frequently Asked Questions About Flights to Boston

Historically, the best time to purchase tickets for flights from Portland to Boston is typically between 28 and 59 days before departure. During this window, the average price for a ticket was $280. Prices tend to be higher for bookings made much further in advance, with tickets purchased 60+ days out averaging $613. Even closer to departure, within 7-13 days, the average price rises to $302.

Across the trailing quarter, a good deal for a flight from Portland to Boston is considered to be $317 or less. The median price for this route over the trailing 90 days was $477. Prices at the higher end typically reached $660. Therefore, if you find a ticket at or below $317, it is historically a favorable price.

Historically, the cheapest months to fly from Portland to Boston are January, April, and February. January typically sees a median price of $119, while April has a median price of $194. February also offers competitive pricing, with a median of $269. This contrasts with the annual median price of $477 for this route.

Related routes

Consider alternative routes from Portland

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