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$234+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in September or November, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Find 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 November 19, 2025.

This American Airlines deal was found by Cheapflights users on 11/16. 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 12/1510:45 pmPDX - EYW
1 stop9h 17mAmerican Airlines
Mon 12/222:28 pmEYW - PDX
1 stop10h 31mAmerican Airlines
Deal found 11/16$349
This American Airlines deal was found by Cheapflights users on 11/17. 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.
Tue 12/25:30 amPDX - EYW
2 stops10h 53mAmerican Airlines
Sat 12/64:59 pmEYW - PDX
1 stop9h 24mAmerican Airlines
Deal found 11/17$394
This American Airlines deal was found by Cheapflights users on 11/19. 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 11/255:30 amPDX - EYW
1 stop7h 59mAmerican Airlines
Tue 12/22:39 pmEYW - PDX
1 stop9h 41mAmerican Airlines
Deal found 11/19$497
This Delta deal was found by Cheapflights users on 11/19. 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 11/2412:35 amPDX - EYW
2 stops10h 28mDelta
Tue 12/23:02 pmEYW - PDX
1 stop10h 17mDelta
Deal found 11/19$633

Cheap 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 November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Delta)

One-way from

$234
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$508
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
One-way flight from Portland 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 ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 19, 2025.
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

Fri 2/6

6:00 am-9:47 pm

2 stops12h 47m

Key West

Wed 2/11

4:37 pm-11:46 pm

1 stop10h 09m

$314

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 1/10

6:50 am-7:40 pm

1 stop9h 50m

Key West

Wed 1/14

7:10 am-4:30 pm

2 stops12h 20m

$314

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 12/15

11:59 pm-2:54 pm

2 stops11h 55m

Key West

Mon 12/22

2:28 pm-9:59 pm

1 stop10h 31m

$354

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 1/8

10:15 pm-1:03 pm

2 stops11h 48m

Key West

Mon 1/12

7:08 am-5:52 pm

2 stops13h 44m

$359

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 2/6

6:50 am-7:40 pm

1 stop9h 50m

Key West

Wed 2/11

2:45 pm-10:15 pm

1 stop10h 30m

$389

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 2/22

6:58 pm-12:21 pm

3 stops38h 23m

$234

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 2/22

10:55 pm-7:24 pm

1 stop17h 29m

$303

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 2/21

12:40 am-5:12 pm

2 stops13h 32m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland-Key West flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

How far ahead should I book a flight from Portland to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Key West. Price data was last updated on November 14, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Key West, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 November 19, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, 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
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

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
8,004 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

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.
United Airlines
7.4
Good
9,025 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

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
11,046 reviews
Delta
7.9
Good
8,004 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.1

Overall

7.9

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 $314, American Airlines can have you in Key West from Portland in 9h 50m. Portland and Key West are separated by a distance of 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Delta, at $261, was found to be the cheapest airline from Portland to Key West.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Delta is priced at 59% 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

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Top 3 airlines flying from Portland to Key West

Discover the top 3 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$288Average$602FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$333Average$622FlexibilityNo cancel feeOn-time69%

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