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$206+ 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
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/17. 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 12/187:00 amBOI - EYW
1 stop7h 30mAmerican Airlines
Thu 12/252:28 pmEYW - BOI
1 stop9h 36mAmerican Airlines
Deal found 12/17$529
This Delta deal was found by Cheapflights users on 12/17. 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 12/185:50 amBOI - EYW
2 stops9h 25mDelta
Thu 12/251:02 pmEYW - BOI
2 stops12h 51mDelta
Deal found 12/17$539
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/185:30 amPDX - EYW
2 stops11h 36mDelta
Sat 12/204:47 pmEYW - PDX
1 stop8h 32mDelta
Deal found 12/16$542
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.
Thu 12/1811:21 pmPDX - EYW
1 stop9h 13mAmerican Airlines
Sat 12/202:52 pmEYW - PDX
1 stop10h 07mAmerican Airlines
Deal found 12/16$596
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.
Wed 12/3110:21 pmPDX - EYW
1 stop10h 47mAmerican Airlines
Sun 1/44:03 pmEYW - PDX
1 stop11h 56mAmerican Airlines
Deal found 12/16$910
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/182:40 pmBOI - EYW
3 stops19h 54mUnited Airlines
Thu 12/251:25 pmEYW - BOI
2 stops11h 15mUnited Airlines
Deal found 12/17$2,044

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$298
(American Airlines)

One-way from

$206
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$616
Provider with most accurate pricing for Portland-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Key West flights.
Search Deals
From Oregon to Key West
Search Deals
One-way flight from Oregon to Key West
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Tue 3/3

7:00 am-4:19 pm

1 stop7h 19m

Key West

Tue 3/10

2:40 pm-10:36 pm

1 stop9h 56m

$329

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 2/11

6:00 am-9:47 pm

2 stops12h 47m

Key West

Wed 2/18

4:02 pm-11:59 pm

1 stop10h 57m

$334

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 2/6

7:38 am-11:56 pm

2 stops13h 18m

Key West

Wed 2/11

12:00 pm-8:24 pm

2 stops11h 24m

$339

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 1/2

5:33 am-4:30 pm

1 stop7h 57m

Key West

Sat 1/31

6:06 am-5:52 pm

2 stops14h 46m

$364

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 1/17

11:05 pm-1:03 pm

1 stop10h 58m

Key West

Sat 1/24

12:22 pm-6:56 pm

1 stop9h 34m

$366

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 1/17

10:15 pm-1:03 pm

2 stops11h 48m

Key West

Sat 1/24

7:15 am-7:02 pm

2 stops14h 47m

$391

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 1/24

11:05 pm-1:03 pm

1 stop10h 58m

Key West

Wed 1/28

2:25 pm-9:49 pm

1 stop10h 24m

$429

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 1/10

11:05 pm-1:03 pm

1 stop10h 58m

Key West

Wed 1/14

2:25 pm-9:49 pm

1 stop10h 24m

$429

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 2/21

6:41 am-10:54 pm

2 stops14h 13m

Key West

Tue 2/24

7:54 pm-11:01 am

2 stops17h 07m

$451

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 1/31

7:20 am-11:56 pm

2 stops14h 36m

Key West

Wed 2/4

7:45 pm-12:07 pm

2 stops18h 22m

$454

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 17 results
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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 $715). 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 December 18, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 19% on flights from Oregon to Key West by exploring options for tickets at noon.

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 can get you from Oregon to Key West in just under 7h 19m. Your travel time can differ by up to . Airlines will cover a distance of 2342 mi.

  • 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 $715). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$595FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$688FlexibilityNo cancel feeOn-time69%

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