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$160+ Cheap flights from Westchester County to Oregon

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — PDX
Jan 15 — Jan 221
Thu 1/15
Thu 1/22
1 adult, Economy
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Cheap flight deals from Westchester County to Oregon

Cheapest flights from Westchester County to Oregon
Explore the most affordable flight options available from Westchester County to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 16, 2025.

This American Airlines deal was found by Cheapflights users on 12/16. 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.
Sat 12/201:35 pmHPN - PDX
2 stops13h 00mAmerican Airlines
Mon 12/225:33 amPDX - HPN
2 stops11h 54mAmerican Airlines
Deal found 12/16$891
This Alaska Airlines deal was found by Cheapflights users on 12/16. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/205:56 pmHPN - PDX
2 stops18h 48mAlaska Airlines
Mon 12/2211:00 pmPDX - HPN
1 stop9h 29mAlaska Airlines
Deal found 12/16$920
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:16 pmHPN - PDX
2 stops9h 43mDelta
Sat 1/36:15 amPDX - HPN
1 stop7h 21mDelta
Deal found 12/15$983
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/306:27 amHPN - PDX
1 stop10h 45mAmerican Airlines
Sat 1/310:21 pmPDX - HPN
1 stop8h 08mAmerican Airlines
Deal found 12/15$997
This Delta deal was found by Cheapflights users on 12/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/155:17 pmHPN - PDX
1 stop7h 58mDelta
Thu 12/186:15 amPDX - HPN
1 stop7h 22mDelta
Deal found 12/15$4,243

Find flight deals from Westchester County to Oregon

Keep the following information in mind while searching for Westchester County to Oregon flight deals. Data was last updated December 16, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$313
(Delta)

One-way from

$160
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$594
Provider with most accurate pricing for New York (NYC)-Portland flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Portland flights.
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From Westchester County to Oregon
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One-way flight from Westchester County to Oregon
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County to Oregon 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 December 16, 2025.
Use the filters below to find and compare flights from Westchester County to Oregon that are best for you.

Fly from

Westchester County

Fly to

Oregon

Route

Depart

Return

Price

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Wed 1/14

3:10 pm-8:12 pm

1 stop8h 02m

Portland

Wed 1/21

9:45 pm-9:48 am

1 stop9h 03m

$327

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Tue 1/6

10:00 am-8:27 pm

2 stops13h 27m

Portland

Sun 1/11

10:15 pm-10:30 am

1 stop9h 15m

$337

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Fri 1/9

5:12 pm-12:17 am

2 stops10h 05m

Portland

Mon 1/12

6:00 am-4:32 pm

1 stop7h 32m

$342

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Fri 5/29

3:15 pm-11:41 pm

2 stops11h 26m

Portland

Tue 6/2

10:55 pm-11:44 am

1 stop9h 49m

$363

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Wed 5/27

3:15 pm-11:41 pm

2 stops11h 26m

Portland

Tue 6/2

10:55 pm-11:44 am

1 stop9h 49m

$363

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Fri 5/8

3:15 pm-11:41 pm

2 stops11h 26m

Portland

Tue 5/12

9:45 pm-9:52 am

1 stop9h 07m

$372

White PlainsBoise

HPN - BOI

HPNBOI

White Plains Westchester County

Wed 4/22

4:19 pm-10:38 pm

1 stop8h 19m

Boise Air Term. Gowen Fld

Sun 4/26

11:30 pm-9:52 am

1 stop8h 22m

$394

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Thu 5/28

3:15 pm-11:41 pm

2 stops11h 26m

Portland

Wed 6/3

6:15 am-4:40 pm

1 stop7h 25m

$403

White PlainsPortland

HPN - PDX

HPNPDX

White Plains Westchester County

Thu 5/28

6:00 am-1:14 pm

1 stop10h 14m

Portland

Tue 6/2

10:55 pm-11:44 am

1 stop9h 49m

$419

White PlainsRedmond

HPN - RDM

HPNRDM

White Plains Westchester County

Sat 2/7

12:00 pm-9:15 pm

2 stops12h 15m

Bend/Redmond

Wed 2/11

5:52 am-11:00 pm

2 stops14h 08m

$463

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 25 results
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Best time to book a flight from Westchester County to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Westchester County 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 Westchester County to Oregon

What is the cheapest month to book a flight from Westchester County to Oregon?

Currently, November is the cheapest month in which you can book a flight from Westchester County to Oregon (average of $261). Flying from Westchester County to Oregon in January is currently the most expensive (average of $476). 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 Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated December 16, 2025.
See what other customers who have flown with Delta and American Airlines from Westchester County to Oregon have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,008 reviews

Food

7.3

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
7.9
Good
8,008 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
11,049 reviews
Delta
7.9
Good
8,008 reviews

Food

7.3

Comfort

7.9

Boarding

8.1

Overall

7.9

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Oregon. 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 Westchester County to Oregon?

    Airlines like Delta, American Airlines, and Alaska Airlines fly from Westchester County to Oregon in about 8h 02m. The time it takes to get you to your destination can typically vary by up to 5h 25m. The distance between Westchester County and Oregon is about 2437 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Westchester County to Oregon one-way?

    One-way options have recently been found by users for as low as $138 on Delta. Other airlines that offer cheap prices include Alaska Airlines from $218 and American Airlines from $278 one-way.

  • Can I find deals for flights from Westchester County to Oregon that include hotel bookings?

    Yes. In addition to deals on Westchester County to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Oregon?

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

  • Can I find deals for business class flights from Westchester County to Oregon?

    Yes. Cheapflights offers flight deals from Westchester County to Oregon 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 Westchester County to Oregon?

    Currently, November is the cheapest month in which you can book a flight from Westchester County to Oregon (average of $261). Flying from Westchester County to Oregon in January is currently the most expensive (average of $476). 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

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Alternative routes for Westchester County to Oregon

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Westchester County to Oregon

Discover the top 2 airlines that operate flights from Westchester County to Oregon. 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 December 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$252Average$447FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$312Average$464FlexibilityNo cancel feeOn-time71%

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