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Key West

$303+ Cheap flights from Oregon to Key West (EYW)

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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Oregon to Key West

Keep the following information in mind while searching for Oregon to Key West flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$303
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$797
Provider with most accurate pricing for Portland-Key West flight deals.
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Provider most trusted by Cheapflights users for Portland-Key West flights.
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From Oregon to Key West
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One-way flight from Oregon to Key West
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Highest demand for flights based on searches. 8% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($29 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Oregon to Key West

Cheapest flights from Oregon to Key West
Explore the most affordable flight options available from Oregon to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This Delta deal was found by Cheapflights users on 10/30. 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.
Fri 11/285:30 amPDX - EYW
2 stops11h 23mDelta
Mon 12/87:40 amEYW - PDX
2 stops16h 12mDelta
Deal found 10/30$589
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Fri 11/2810:45 pmPDX - EYW
1 stop9h 37mAmerican Airlines
Mon 12/84:10 pmEYW - PDX
1 stop10h 42mAmerican Airlines
Deal found 10/30$623
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/197:00 amBOI - EYW
2 stops12h 48mAmerican Airlines
Wed 11/267:53 pmEYW - BOI
2 stops16h 44mAmerican Airlines
Deal found 10/27$675
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Wed 12/243:52 pmPDX - EYW
2 stops17h 42mUnited Airlines
Mon 12/294:29 pmEYW - PDX
1 stop30h 14mUnited Airlines
Deal found 10/29$710
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/2410:39 pmPDX - EYW
1 stop9h 27mAmerican Airlines
Mon 12/2911:47 amEYW - PDX
1 stop16h 12mAmerican Airlines
Deal found 10/29$757
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Wed 11/192:11 pmBOI - EYW
2 stops21h 53mUnited Airlines
Wed 11/263:00 pmEYW - BOI
3 stops24h 31mUnited Airlines
Deal found 10/27$910
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/2911:55 pmPDX - EYW
1 stop9h 39mUnited Airlines
Fri 1/24:08 pmEYW - PDX
1 stop9h 32mUnited Airlines
Deal found 10/30$1,054
This United Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/2911:55 pmPDX - EYW
1 stop9h 39mUnited Airlines
Sat 1/34:29 pmEYW - PDX
2 stops20h 32mUnited Airlines
Deal found 10/30$1,086
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sun 11/231:33 pmBOI - EYW
1 stop21h 14mAmerican Airlines
Fri 11/287:00 amEYW - BOI
1 stop17h 07mAmerican Airlines
Deal found 10/30$1,100
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Sun 12/2811:21 pmPDX - EYW
1 stop11h 26mAmerican Airlines
Sun 1/412:55 pmEYW - PDX
1 stop11h 24mAmerican Airlines
Deal found 10/30$1,115
This American Airlines deal was found by Cheapflights users on 10/30. 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.
Mon 12/2910:49 pmPDX - EYW
1 stop9h 17mAmerican Airlines
Fri 1/24:40 pmEYW - PDX
2 stops11h 14mAmerican Airlines
Deal found 10/30$1,120

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oregon to Key West 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 October 30, 2025.
Use the filters below to find and compare flights from Oregon to Key West that are best for you.

Fly from

Oregon

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 1/22

11:01 pm-10:57 am

1 stop8h 56m

Key West

Mon 1/26

4:37 pm-11:46 pm

1 stop10h 09m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 1/21

12:40 am-1:48 pm

2 stops10h 08m

Key West

Mon 1/26

7:10 am-4:30 pm

2 stops12h 20m

$402

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 1/7

6:00 am-11:56 pm

2 stops14h 56m

Key West

Sat 1/10

1:22 pm-8:17 pm

1 stop9h 55m

$412

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 4/2

9:13 am-11:59 pm

2 stops11h 46m

Key West

Thu 4/30

3:55 pm-8:54 pm

1 stop7h 59m

$506

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 11/28

5:30 am-7:53 pm

2 stops11h 23m

Key West

Mon 12/8

7:40 am-8:52 pm

2 stops16h 12m

$589

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Wed 11/19

7:00 am-9:48 pm

2 stops12h 48m

Key West

Wed 11/26

7:53 pm-10:37 am

2 stops16h 44m

$675

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Wed 11/19

2:11 pm-2:04 pm

2 stops21h 53m

Key West

Wed 11/26

3:00 pm-1:31 pm

3 stops24h 31m

$910

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sun 11/23

1:33 pm-12:47 pm

1 stop21h 14m

Key West

Fri 11/28

7:00 am-10:07 pm

1 stop17h 07m

$1,100

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 1/25

11:01 pm-1:03 pm

1 stop11h 02m

$303

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 1/25

7:00 am-4:22 pm

3 stops30h 22m

$474

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Best time to book a flight from Oregon to Key West

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

What is the cheapest month to book a flight from Oregon to Key West?

Currently, June is the cheapest month in which you can book a flight from Oregon to Key West (average of $242). Flying from Oregon to Key West in October is currently the most expensive (average of $603). 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.

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

Find hourly flight availability from Oregon to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 23% on flights from Oregon to Key West by exploring options for tickets at noon.

How much does it cost to fly round-trip from Oregon to Key West?

Related info for your journey

Find useful and relevant information for your journey from Oregon to Key West. 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 into for flights to Key West from Oregon?

    Located just 2.6 mi from the city center, Key West (EYW) is the airport most travelers will use when flying to Key West from Oregon.

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

    American Airlines, Delta, and United Airlines can get you from Oregon to Key West in just under 8h 56m. Your travel time can differ by up to 12h 57m. Airlines will cover a distance of 2685 mi. This flight may include one or multiple stops.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon to Key West 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 Oregon to Key West?

    Currently, June is the cheapest month in which you can book a flight from Oregon to Key West (average of $242). Flying from Oregon to Key West in October is currently the most expensive (average of $603). 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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Top 3 airlines flying from Oregon to Key West

Discover the top 3 airlines that operate flights from Oregon to Key West. 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$610FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$601FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$728FlexibilityNo cancel feeOn-time69%

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