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$309+ Cheap flights from Watertown, NY to Portland (ART - PDX)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
ART — PDX
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Watertown to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Watertown (ART) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$309
(American Airlines)
From Watertown to Portland
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Find flight deals from Watertown to Portland

Cheapest flights from Watertown to Portland
Explore the most affordable flight options available from Watertown to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/302:45 pmART - PDX
2 stops12h 13mAmerican Airlines
Tue 11/45:30 amPDX - ART
2 stops14h 26mAmerican Airlines
Deal found 9/16$309

Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Watertown to Portland that are best for you.

Fly from

Watertown

Fly to

Portland

Route

Depart

Return

Price

WatertownPortland

ART - PDX

ARTPDX

Watertown

Thu 10/30

2:45 pm-11:58 pm

2 stops12h 13m

Portland

Tue 11/4

5:30 am-10:56 pm

2 stops14h 26m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Best time to book a flight from Watertown to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Watertown with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Watertown to Portland

What is the cheapest month to book a flight from Watertown, New York to Portland?

Currently, November is the cheapest month in which you can book a flight from Watertown, New York to Portland (average of $277). Flying from Watertown, New York to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated September 17, 2025.
Read through reviews of airlines operating flights from Watertown to Portland, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Entertainment

6.9

Food

6.4

Comfort

7.2

Overall

7.2

Boarding

7.5

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

Related info for your journey

Find useful and relevant information for your journey from Watertown to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Watertown, New York to Portland?

    Departing from Watertown, New York to Portland will take you 12h 13m. The distance between Watertown, New York and Portland is about 2252 mi.

  • What is the cheapest airline to fly from Watertown, New York to Portland round-trip?

    Currently priced at $368, American Airlines will fly you from Watertown, New York to Portland and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip.

  • Can I find deals for flights from Watertown to Portland that include hotel bookings?

    Yes. In addition to deals on Watertown to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Watertown to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Watertown to Portland.

  • Can I find deals for business class flights from Watertown to Portland?

    Yes. Cheapflights offers flight deals from Watertown to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Watertown, New York to Portland?

    Currently, November is the cheapest month in which you can book a flight from Watertown, New York to Portland (average of $277). Flying from Watertown, New York to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Seaside
Beaverton
Clackamas
McMinnville
Lake Oswego
Hillsboro
Cannon Beach
Long Beach
Longview
Lincoln City
Tigard
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Troutdale
Gresham
Silverton

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Alternative routes for Watertown to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Watertown to Portland

Discover the top airline that operate flights from Watertown to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$368Average$538FlexibilityNo cancel feeOn-time71%

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