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When’s a good time to book a flight from Portland to Boston?

What’s the cheapest day of the week to fly from Portland to Boston?

What is the cheapest month to fly from Portland to Boston?

‡This information is based on historical data from the last 365 days.

Finding Affordable Flights from Portland to Boston
  • Plan Ahead - One of the keys to securing cheap flights from Portland to Boston is to plan your trip well in advance. Airlines often offer lower prices for those who book tickets months ahead. Keep an eye on special promotions and sales events, which can yield significant savings.
  • Flexibility is Key - Being flexible with your travel dates can also lead to substantial cost savings. Consider flying during off-peak seasons or on weekdays when prices tend to be lower.
  • Set Price Alerts - To keep tabs on flight prices, consider setting up fare alerts. These alerts will notify you when fares from Portland to Boston drop, giving you the opportunity to grab cheap deals.
  • Consider Nearby Airports - If Boston has multiple airports, check the prices at each one. Sometimes, flying into a nearby airport and then taking a short train or bus ride to your destination can be a much cheaper option.
  • Bundle and Save - Booking your flight and accommodation together as a package can often result in significant savings. CheapOair offers these bundled deals, so make sure to explore this option.

When is the Cheapest Time to Book Flights from Portland to Boston?

Got flexible travel dates? Use our flight data from the past year to discover ideal times to fly from Portland to Boston. Find out which months and days typically offer lower fares and score our best savings.

CheapOair provides the predicted prices for one-way trips or round-trips with a duration of 7 days for domestic and 14 days for international trips based on historical data and available flight information. Graphs are estimates only. Prices are subject to change and can't be guaranteed until ticketed.
Estimated price for
Round-trip

‡Graphs are estimates only. Based on historical data and available flight information. Prices are subject to change and cannot be guaranteed until ticketed.

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Portland to Boston Flight Route Information

Travel Distance:2,532 Miles
Airlines Flying This Route: JetBlue Airways, Alaska Airlines, Qatar Airways
Weekly Flights:9
Avg. Flight Duration:5.19 Hours

Insights About Flying from Portland to Boston

Q. Which is the high season to travel from Portland to Boston?

A. The month of August is considered the high season for flying from PDX to BOS. Traveling during the high season can affect ticket prices and availability, making this data crucial for trip planning.

Q. How many direct flights are available from PDX to BOS?

A. There are a total of 38 direct flights from Portland to Boston. For travelers seeking convenience and shorter travel times, this data is important when choosing flight options.

Q. Which is the low season to travel from Portland to Boston?

A. April is considered the low season for traveling from Portland to Boston, Massachusetts. Travelers looking for cost-effective options and fewer crowds may consider traveling during this period.

Q. How many daily flights are there between Portland to Boston?

A. There are as many as 1 daily flights available for travelers between PDX to BOS. This data offers flexibility in choosing departure times that best suit your schedule.

Q. Which is the busiest day for passengers flying between Portland to Boston?

A. Monday are the busiest days for passengers flying between Portland to Boston. Knowing the peak travel day can help you plan your trip to avoid overcrowded flights or airports.

Q. At what time does the last flight depart to Boston?

A. The last flight to Boston typically departs between 10:00PM - 11:00PM. Travelers who prefer late-night departures will find this information valuable for planning their journey.

Q. What percentage of travelers spent an average of 5 days in Boston, Massachusetts?

A. Approximately 38.78% of travelers spent an average of 5 days exploring Boston. This information can assist in planning the duration of your stay in Boston

Q. What percentage of PDX to BOS flyers traveled with kids under 14?

A. About 5% of passengers on flights from Portland to Boston were accompanied by children under the age of 14. This information is useful if you're planning a family trip and want to know how common it is to travel with young children on this route.

Q. What percentage of Portland to Boston travelers were over 60 years old?

A. A notable 20% of travelers were aged 60 or older. This statistic provides insights for senior travelers or those seeking a mature travel demographic.

Q. What percentage of PDX to BOS travelers were millennials?

A. Millennials make up a significant portion of travelers on this route, accounting for 39% of all passengers. If you're a millennial looking to connect with like-minded travelers, this statistic might interest you.

Q. What percentage of Portland to Boston travelers were female?

A. Almost half of the passengers, approximately 59% were female. Knowing the gender distribution can be useful for solo female travelers or those interested in gender-related travel insights.

Q. What percent of Portland to Boston travellers booked first or business class?

A. 13% of travelers booked first or business class on this route.

Q. At what time the earliest flight departs from Portland?

A. The earliest flight departs at 7:00AM - 8:00AM.

Q. On which days one can have the most flight options in Boston?

A. Monday offer the most flight options in Boston.

§ All flight facts are based on last 3 months' data except the highest and lowest booking months that are based on last 3 months' data.

Cheap Flights from Portland to Boston

Looking for flights from Portland to Boston? Look no more, for you�re at the right place. Book cheap flights from Portland to Boston on CheapOair and enjoy great discounts. Whether its leisure or a business trip, we offer the most competitive rates on flight tickets to destinations around the world. Grab PDX to BOS flight deals on CheapOair and save big!

Airports in Portland

The city of Portland is served by Portland International Airport. The airport is located about 19 kilometers northeast of downtown Portland. Portland International Airport offers flights to several destinations such as Mexico City, Amsterdam, New York, Los Angeles, and more. Public transit service to the airport is operated by TriMet, with its MAX Red Line light rail service. Other ground transportation options to and from the airport include car rental, and taxi services.

Explore Boston

The capital city of the Commonwealth of Massachusetts, Boston is also the most populous city in the New England region of the northeastern United States. One of the oldest cities in the United States, Boston is home to a plethora of historic places making it an excellent city to visit for history buffs. One can enjoy a walk through well-off history on the Freedom Trail. Besides the historic attractions, key tourist attractions in the city comprise top seafood restaurants, historic neighborhoods, world-class museums, and picturesque waterfront.

Things to do in Boston

New England Aquarium

New England Aquarium treats history buffs with around 20,000 fish and aquatic animals representing more than 550 species. In the center, there is an artificial Caribbean coral reef featuring a large diversity of tropical fish and underwater life such as turtles, sharks, and moral eels.

Boston Museum of Fine Arts

One of the leading art museums in the US, Boston Museum of Fine Arts is home to a collection of Impressionist paintings, Asian and Persian fine arts, ancient Egyptian treasures, and interesting works from ancient Greece and the Middle East. It is an apt place to visit for art lovers.

Isabella Stewart Gardner Museum

A great place to visit for art and history lovers, Isabella Stewart Gardner Museum is home to assortments including paintings, furniture, sculpture, decorative arts, tapestries, manuscripts, and books displaying the personal taste and expertise of Isabella Stewart Gardner, the creator of the museum. The building is also home to a long green space where there is a beautiful rose garden.

Best Time to Fly to Boston

Boston experiences humid mainland climate with warm summers and winters with chilly rain and snow. The best time to visit the city is from June to October, the Fall season.

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