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$389+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
ART — PDX
Mar 11 — Mar 181
Wed 3/11
Wed 3/18
1 adult, Economy
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Cheap 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 February 9, 2026.

This American Airlines deal was found by Cheapflights users on 2/9. 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.
Tue 2/246:00 am
ART
-
PDX
2 stops14h 13m
American Airlines
Sat 2/286:35 am
PDX
-
ART
2 stops13h 20m
American Airlines
Deal found 2/9$389
This Alaska Airlines deal was found by Cheapflights users on 2/8. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/314:00 pm
ART
-
PDX
2 stops11h 10m
Alaska Airlines
Tue 11/36:07 am
PDX
-
ART
2 stops13h 51m
Alaska Airlines
Deal found 2/8$429
This American Airlines deal was found by Cheapflights users on 2/7. 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.
Wed 7/84:00 pm
ART
-
PDX
1 stop10h 18m
American Airlines
Wed 7/1512:32 pm
PDX
-
ART
1 stop8h 20m
American Airlines
Deal found 2/7$432
This American Airlines deal was found by Cheapflights users on 2/5. 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 3/126:00 am
ART
-
PDX
2 stops18h 07m
American Airlines
Sun 3/1511:59 pm
PDX
-
ART
2 stops12h 20m
American Airlines
Deal found 2/5$542
This American Airlines deal was found by Cheapflights users on 2/8. 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.
Wed 4/811:25 am
ART
-
PDX
2 stops12h 38m
American Airlines
Wed 4/157:13 am
PDX
-
ART
2 stops13h 10m
American Airlines
Deal found 2/8$607
This American Airlines deal was found by Cheapflights users on 2/6. 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.
Sat 2/77:00 am
ART
-
PDX
2 stops15h 02m
American Airlines
Fri 2/206:25 am
PDX
-
ART
2 stops13h 30m
American Airlines
Deal found 2/6$832

Find 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 February 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(American Airlines)
Provider with most accurate pricing for Watertown-Portland flight deals.
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Provider most trusted by Cheapflights users for Watertown-Portland flights.
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From Watertown to Portland
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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 February 9, 2026.
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

Tue 2/24

6:00 am-5:13 pm

2 stops14h 13m

Portland

Sat 2/28

6:35 am-10:55 pm

2 stops13h 20m

$389

WatertownPortland

ART - PDX

ARTPDX

Watertown

Wed 7/8

4:00 pm-11:18 pm

1 stop10h 18m

Portland

Wed 7/15

12:32 pm-11:52 pm

1 stop8h 20m

$432

WatertownPortland

ART - PDX

ARTPDX

Watertown

Thu 3/12

6:00 am-9:07 pm

2 stops18h 07m

Portland

Sun 3/15

11:59 pm-3:19 pm

2 stops12h 20m

$542

WatertownPortland

ART - PDX

ARTPDX

Watertown

Wed 4/8

11:25 am-9:03 pm

2 stops12h 38m

Portland

Wed 4/15

7:13 am-11:23 pm

2 stops13h 10m

$607

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/9

  • Most accurate provider: When it comes to deals on Watertown, New York-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Watertown, New York-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Watertown, New York-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Watertown, New York-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Watertown, New York-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, September is the cheapest month in which you can book a flight from Watertown, New York to Portland (average of $250). Flying from Watertown, New York to Portland in June is currently the most expensive (average of $334). 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 February 9, 2026.
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
11,258 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,258 reviews
American Airlines
7.2
Good
11,258 reviews

Food

6.4

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 14h 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 $328, 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, September is the cheapest month in which you can book a flight from Watertown, New York to Portland (average of $250). Flying from Watertown, New York to Portland in June is currently the most expensive (average of $334). 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
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Gresham

Browse thousands of different options on Cheapflights for your next trip

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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 February 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$328Average$502FlexibilityNo cancel feeOn-time71%

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