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Key West

$309+ Cheap flights from Portland to Key West (PDX - 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Mar 19 — Mar 261
Thu 3/19
Thu 3/26
1 adult, Economy
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Cheap flight deals from Portland to Key West

Cheapest flights from Portland to Key West
Explore the most affordable flight options available from Portland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 17, 2026.

This American Airlines deal was found by Cheapflights users on 2/16. 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.
Mon 3/169:44 pm
PDX
-
EYW
1 stop11h 17m
American Airlines
Mon 3/233:56 pm
EYW
-
PDX
1 stop10h 48m
American Airlines
Deal found 2/16$329
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Fri 4/2411:47 pm
PDX
-
EYW
2 stops10h 21m
American Airlines
Wed 4/292:01 pm
EYW
-
PDX
2 stops12h 56m
American Airlines
Deal found 2/16$339
This American Airlines deal was found by Cheapflights users on 2/14. 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.
Wed 4/226:00 am
PDX
-
EYW
1 stop8h 02m
American Airlines
Wed 4/292:29 pm
EYW
-
PDX
1 stop10h 09m
American Airlines
Deal found 2/14$359
This American Airlines deal was found by Cheapflights users on 2/15. 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 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 8/143:00 pm
EYW
-
PDX
2 stops11h 59m
American Airlines
Deal found 2/15$364
This United Airlines deal was found by Cheapflights users on 2/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:16 pm
PDX
-
EYW
1 stop12h 29m
United Airlines
Thu 5/74:47 pm
EYW
-
PDX
1 stop9h 12m
United Airlines
Deal found 2/13$389
This American Airlines deal was found by Cheapflights users on 2/16. 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.
Tue 3/35:40 am
PDX
-
EYW
1 stop7h 38m
American Airlines
Sat 3/72:06 pm
EYW
-
PDX
2 stops13h 11m
American Airlines
Deal found 2/16$394
This United Airlines deal was found by Cheapflights users on 2/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:00 am
PDX
-
EYW
1 stop8h 19m
United Airlines
Thu 3/194:55 pm
EYW
-
PDX
1 stop9h 18m
United Airlines
Deal found 2/14$409
This Delta deal was found by Cheapflights users on 2/15. 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.
Mon 7/139:45 pm
PDX
-
EYW
1 stop10h 13m
Delta
Tue 7/216:00 pm
EYW
-
PDX
2 stops18h 57m
Delta
Deal found 2/15$418

Find flight deals from Portland to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$329
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$642
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 Portland to Key West
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($33 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 Portland 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 17, 2026.
Use the filters below to find and compare flights from Portland to Key West that are best for you.

Fly from

Portland

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 3/16

9:44 pm-12:01 pm

1 stop11h 17m

Key West

Mon 3/23

3:56 pm-11:44 pm

1 stop10h 48m

$329

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 4/24

11:47 pm-1:08 pm

2 stops10h 21m

Key West

Wed 4/29

2:29 pm-9:38 pm

1 stop10h 09m

$334

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 4/22

6:00 am-5:02 pm

1 stop8h 02m

Key West

Wed 4/29

2:29 pm-9:38 pm

1 stop10h 09m

$359

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 4/30

10:28 pm-10:54 am

1 stop9h 26m

Key West

Thu 5/7

3:58 pm-11:53 pm

1 stop10h 55m

$359

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 3/4

5:40 am-10:22 pm

2 stops13h 42m

Key West

Tue 3/10

3:56 pm-11:44 pm

1 stop10h 48m

$364

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 4/29

7:23 am-10:58 pm

2 stops12h 35m

Key West

Tue 5/19

6:45 am-4:59 pm

2 stops13h 14m

$369

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 4/30

10:15 pm-1:45 pm

1 stop12h 30m

Key West

Wed 5/6

4:47 pm-10:59 pm

1 stop9h 12m

$389

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 4/30

10:16 pm-1:45 pm

1 stop12h 29m

Key West

Thu 5/7

4:47 pm-10:59 pm

1 stop9h 12m

$389

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 6/3

12:23 pm-8:11 am

2 stops40h 48m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 6/3

10:30 pm-1:41 pm

1 stop12h 11m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 15 results
1
2

Compare providers for flights from Portland to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Key West in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Key West

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

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

Currently, June is the cheapest month in which you can book a flight from Portland to Key West (average of $242). Flying from Portland 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.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated February 17, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from Portland to Key West to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,206 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
7.9
Good
8,206 reviews
Delta
7.9
Good
8,206 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
11,294 reviews
Delta
7.9
Good
8,206 reviews

Food

7.2

Overall

7.9

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

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

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

    For as low as $329, American Airlines can have you in Key West from Portland in 11h 17m. Portland and Key West are separated by a distance of 2685 mi.

  • What are the cheapest airlines flying from Portland to Key West round-trip?

    Delta, at $242, was found to be the cheapest airline from Portland to Key West. An alternate airline flying to your destination would be American Airlines. Delta is priced at 60% lower than the current average price of a flight leaving 3 months from now.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Portland to Key West (average of $242). Flying from Portland 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 2 airlines flying from Portland to Key West

Discover the top 2 airlines that operate flights from Portland 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 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$242Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$617FlexibilityNo cancel feeOn-time71%

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