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$353+ Cheap flights from Key West (EYW) 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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Key West to Oregon

Best flights from Key West to Oregon
Discover carefully curated flight deals from Key West to Oregon that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/21. 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 5/144:02 pmEYW - PDX
1 stop10h 00mAmerican Airlines
Sat 5/2311:52 pmPDX - EYW
2 stops12h 30mAmerican Airlines
Deal found 12/21$422
This United Airlines deal was found by Cheapflights users on 12/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/172:05 pmEYW - PDX
1 stop10h 44mUnited Airlines
Tue 1/2011:05 pmPDX - EYW
1 stop10h 58mUnited Airlines
Deal found 12/20$429
This Delta deal was found by Cheapflights users on 12/21. 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.
Thu 5/142:35 pmEYW - PDX
2 stops12h 18mDelta
Sat 5/235:10 pmPDX - EYW
2 stops14h 48mDelta
Deal found 12/21$486

Find flight deals from Key West to Oregon

Keep the following information in mind while searching for Key West to Oregon flight deals. Data was last updated December 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$329
(American Airlines)
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Portland flights.
Search Deals
From Key West to Oregon
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West 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 23, 2025.
Use the filters below to find and compare flights from Key West to Oregon that are best for you.

Fly from

Key West

Fly to

Oregon

Route

Depart

Return

Price

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 5/14

4:02 pm-11:02 pm

1 stop10h 00m

Portland

Sat 5/23

11:52 pm-3:22 pm

2 stops12h 30m

$422

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sat 1/17

2:05 pm-9:49 pm

1 stop10h 44m

Portland

Tue 1/20

11:05 pm-1:03 pm

1 stop10h 58m

$429

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 5/14

2:35 pm-11:53 pm

2 stops12h 18m

Portland

Sat 5/23

5:10 pm-10:58 am

2 stops14h 48m

$486

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sat 5/23

4:05 pm-10:08 pm

1 stop9h 03m

$353

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 12/31

4:03 pm-12:59 am

1 stop11h 56m

$371

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sat 5/23

2:00 pm-11:07 pm

2 stops12h 07m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Best time to book a flight from Key West to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon from Key West 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 Key West to Oregon

What is the cheapest time of day to fly from EYW to OR?

Find hourly flight availability from Key West to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

One of the essential ways to save on airfare from Key West to Oregon is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 44% on airfare.

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 23, 2025.
Read reviews from past customers who have flown American Airlines from Key West to Oregon. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,054 reviews
American Airlines
7.2
Good
11,054 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

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

  • What airport do you fly from for flights from Key West to Oregon?

    Key West (EYW) is the airport you will fly out of if you book a flight from Key West to Oregon. It is only a 2.6 mi journey to Key West (EYW) from Key West’s city center.

  • How long is the flight from Key West to Oregon?

    For as low as $422, American Airlines can have you in Oregon from Key West in 10h. The distance between Key West and Oregon is about 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • Can I find deals for flights from Key West to Oregon that include hotel bookings?

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

  • How can I find direct flights from Key West to Oregon?

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

  • Can I find deals for business class flights from Key West to Oregon?

    Yes. Cheapflights offers flight deals from Key West 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.

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Top airline flying from Key West to Oregon

Discover the top airline that operate flights from Key West 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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