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Key West

$203+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Mar 8 — Mar 151
Sun 3/8
Sun 3/15
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 February 6, 2026.

This American Airlines deal was found by Cheapflights users on 2/4. 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 10/315:55 am
PDX
-
EYW
1 stop7h 17m
American Airlines
Sat 11/712:40 pm
EYW
-
PDX
1 stop11h 35m
American Airlines
Deal found 2/4$329
This American Airlines deal was found by Cheapflights users on 2/5. 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 4/228:00 am
PDX
-
EYW
2 stops11h 58m
American Airlines
Wed 4/292:29 pm
EYW
-
PDX
1 stop10h 09m
American Airlines
Deal found 2/5$334
This American Airlines deal was found by Cheapflights users on 2/3. 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 8/810:30 pm
PDX
-
EYW
1 stop12h 12m
American Airlines
Fri 8/142:31 pm
EYW
-
PDX
1 stop9h 46m
American Airlines
Deal found 2/3$359
This American Airlines deal was found by Cheapflights users on 2/5. 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 3/37:00 am
BOI
-
EYW
1 stop7h 18m
American Airlines
Tue 3/107:42 pm
EYW
-
BOI
2 stops18h 18m
American Airlines
Deal found 2/5$366
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Fri 5/110:16 pm
PDX
-
EYW
1 stop12h 29m
United Airlines
Fri 5/84:47 pm
EYW
-
PDX
1 stop9h 12m
United Airlines
Deal found 2/4$389
This Delta deal was found by Cheapflights users on 2/3. 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.
Wed 5/278:06 pm
PDX
-
EYW
2 stops11h 47m
Delta
Sat 5/301:00 pm
EYW
-
PDX
1 stop8h 38m
Delta
Deal found 2/3$394
This American Airlines deal was found by Cheapflights users on 2/4. 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 4/156:00 am
PDX
-
EYW
1 stop8h 02m
American Airlines
Wed 4/223:58 pm
EYW
-
PDX
1 stop10h 55m
American Airlines
Deal found 2/4$417
This American Airlines deal was found by Cheapflights users on 2/4. 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 8/126:59 am
BOI
-
EYW
1 stop7h 09m
American Airlines
Tue 8/182:31 pm
EYW
-
BOI
1 stop9h 09m
American Airlines
Deal found 2/4$417
This United Airlines deal was found by Cheapflights users on 2/5. 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 3/410:38 pm
PDX
-
EYW
1 stop11h 45m
United Airlines
Wed 3/114:05 pm
EYW
-
PDX
1 stop9h 40m
United Airlines
Deal found 2/5$421
This American Airlines deal was found by Cheapflights users on 2/3. 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 3/411:35 pm
PDX
-
EYW
2 stops13h 22m
American Airlines
Tue 3/103:56 pm
EYW
-
PDX
1 stop10h 48m
American Airlines
Deal found 2/3$422
This American Airlines deal was found by Cheapflights users on 2/3. 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 2/107:20 am
BOI
-
EYW
2 stops14h 36m
American Airlines
Thu 2/192:45 pm
EYW
-
BOI
1 stop9h 37m
American Airlines
Deal found 2/3$444
This American Airlines deal was found by Cheapflights users on 2/3. 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 7/196:44 am
BOI
-
EYW
1 stop8h 08m
American Airlines
Thu 7/302:22 pm
EYW
-
BOI
1 stop10h 15m
American Airlines
Deal found 2/3$458

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 February 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(American Airlines)

One-way from

$203
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$641
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. 11% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($32 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 6, 2026.
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

Wed 4/22

8:00 am-10:58 pm

2 stops11h 58m

Key West

Wed 4/29

2:29 pm-9:38 pm

1 stop10h 09m

$334

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 3/1

9:44 pm-11:11 am

1 stop10h 27m

Key West

Tue 3/10

3:56 pm-11:44 pm

1 stop10h 48m

$359

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 4/15

8:00 am-10:58 pm

2 stops11h 58m

Key West

Wed 4/22

3:58 pm-11:53 pm

1 stop10h 55m

$364

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Tue 3/3

7:00 am-4:18 pm

1 stop7h 18m

Key West

Tue 3/10

7:42 pm-12:00 pm

2 stops18h 18m

$366

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 5/1

10:16 pm-1:45 pm

1 stop12h 29m

Key West

Fri 5/8

4:47 pm-10:59 pm

1 stop9h 12m

$389

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Mon 7/20

6:00 pm-12:15 pm

2 stops16h 15m

Key West

Thu 7/30

2:22 pm-10:37 pm

1 stop10h 15m

$452

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Mon 7/20

11:30 pm-10:58 am

1 stop9h 28m

Key West

Thu 7/30

2:35 pm-10:38 pm

1 stop10h 03m

$475

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 3/7

7:00 am-10:37 pm

2 stops13h 37m

Key West

Thu 3/12

2:25 pm-10:23 pm

1 stop9h 58m

$508

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Wed 5/6

6:43 am-10:36 pm

2 stops13h 53m

Key West

Tue 5/12

2:29 pm-10:38 pm

1 stop10h 09m

$541

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Thu 5/7

11:39 pm-10:53 am

1 stop9h 14m

Key West

Tue 5/12

2:00 pm-10:28 pm

1 stop10h 28m

$567

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 15 results
1
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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.

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 11h 58m. Your travel time can differ by up to . Airlines will cover a distance of 2685 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

Browse thousands of different options on Cheapflights for your next trip

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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 February 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$581FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$607FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$648Average$753FlexibilityNo cancel feeOn-time69%

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