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Key West

$168+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
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 septiembre 15, 2025.

Round-trip from

$379
(American Airlines)

One-way from

$168
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$414
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. 12% potential increase in price ($85 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($33 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 15, 2025.

This Delta deal was found by Cheapflights users on 9/15. 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.
mar. 9/306:00 amPDX - EYW
1 stop8h 15mDelta
sáb. 10/411:50 amEYW - PDX
1 stop10h 08mDelta
Deal found 9/15$465
This American Airlines deal was found by Cheapflights users on 9/14. 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.
lun. 10/209:52 pmPDX - EYW
2 stops10h 00mAmerican Airlines
jue. 11/64:18 pmEYW - PDX
1 stop10h 13mAmerican Airlines
Deal found 9/14$480
This Delta deal was found by Cheapflights users on 9/14. 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.
lun. 10/1310:10 pmPDX - EYW
1 stop10h 17mDelta
lun. 10/201:57 pmEYW - PDX
1 stop11h 11mDelta
Deal found 9/14$511
This American Airlines deal was found by Cheapflights users on 9/13. 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.
jue. 10/1611:59 pmPDX - EYW
2 stops14h 17mAmerican Airlines
mar. 10/212:32 pmEYW - PDX
1 stop10h 17mAmerican Airlines
Deal found 9/13$526
This American Airlines deal was found by Cheapflights users on 9/14. 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.
vie. 11/215:30 amPDX - EYW
1 stop7h 59mAmerican Airlines
mar. 11/254:10 pmEYW - PDX
1 stop10h 21mAmerican Airlines
Deal found 9/14$552
This Delta deal was found by Cheapflights users on 9/13. 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.
lun. 9/2910:05 pmPDX - EYW
1 stop9h 50mDelta
lun. 10/61:57 pmEYW - PDX
1 stop11h 11mDelta
Deal found 9/13$557
This American Airlines deal was found by Cheapflights users on 9/14. 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.
jue. 9/185:22 pmBOI - EYW
2 stops15h 51mAmerican Airlines
sáb. 9/2011:25 amEYW - BOI
2 stops12h 23mAmerican Airlines
Deal found 9/14$569
This Delta deal was found by Cheapflights users on 9/13. 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.
sáb. 9/275:45 amBOI - EYW
2 stops12h 22mDelta
dom. 9/287:00 amEYW - BOI
1 stop7h 30mDelta
Deal found 9/13$749
This American Airlines deal was found by Cheapflights users on 9/13. 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.
sáb. 9/277:00 amBOI - EYW
2 stops9h 59mAmerican Airlines
dom. 9/287:31 pmEYW - BOI
2 stops19h 17mAmerican Airlines
Deal found 9/13$922

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 septiembre 15, 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

mar. 9/30

6:00 am-5:15 pm

1 stop8h 15m

Key West

sáb. 10/4

11:50 am-6:58 pm

1 stop10h 08m

$465

PortlandKey West

PDX - EYW

PDXEYW

Portland

lun. 10/20

5:34 am-4:13 pm

1 stop7h 39m

Key West

jue. 11/6

4:18 pm-11:31 pm

1 stop10h 13m

$475

PortlandKey West

PDX - EYW

PDXEYW

Portland

lun. 10/13

10:10 pm-11:27 am

1 stop10h 17m

Key West

lun. 10/20

1:57 pm-10:08 pm

1 stop11h 11m

$511

PortlandKey West

PDX - EYW

PDXEYW

Portland

jue. 10/16

11:59 pm-5:16 pm

2 stops14h 17m

Key West

mar. 10/21

2:32 pm-9:49 pm

1 stop10h 17m

$526

PortlandKey West

PDX - EYW

PDXEYW

Portland

lun. 9/29

10:05 pm-10:55 am

1 stop9h 50m

Key West

lun. 10/6

1:57 pm-10:08 pm

1 stop11h 11m

$557

PortlandKey West

PDX - EYW

PDXEYW

Portland

vie. 11/21

5:30 am-4:29 pm

1 stop7h 59m

Key West

mar. 11/25

4:10 pm-12:50 am

2 stops11h 40m

$557

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

jue. 9/18

5:22 pm-11:13 am

2 stops15h 51m

Key West

sáb. 9/20

11:25 am-9:48 pm

2 stops12h 23m

$569

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

sáb. 9/27

5:45 am-8:07 pm

2 stops12h 22m

Key West

dom. 9/28

7:00 am-12:30 pm

1 stop7h 30m

$749

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

sáb. 9/27

7:00 am-6:59 pm

2 stops9h 59m

Key West

dom. 9/28

7:31 pm-12:48 pm

2 stops19h 17m

$922

PortlandKey West

PDX - EYW

PDXEYW

Portland

sáb. 10/25

12:43 pm-8:15 am

2 stops40h 32m

$168

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon to Key West in March is currently the most expensive (average of $491). 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 septiembre 15, 2025.

When flying from Oregon to Key West, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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?

    Delta and American Airlines can get you from Oregon to Key West in just under 7h 39m. Your travel time can differ by up to 36m. 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, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon to Key West in March is currently the most expensive (average of $491). 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 Oregon to Key West

See prices for flight routes from nearby airports that may be better suited for you.
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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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$591FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$347Average$740FlexibilityNo cancel feeOn-time69%

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