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$168+ 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 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
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in September or January, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

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 September 15, 2025.

Round-trip from

$384
(United Airlines)

One-way from

$168
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$414
From Portland to Key West
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One-way flight from Portland 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 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 September 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.
Tue 9/306:00 amPDX - EYW
1 stop8h 15mDelta
Sat 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.
Mon 10/209:52 pmPDX - EYW
2 stops10h 00mAmerican Airlines
Thu 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.
Mon 10/1310:10 pmPDX - EYW
1 stop10h 17mDelta
Mon 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.
Thu 10/1611:59 pmPDX - EYW
2 stops14h 17mAmerican Airlines
Tue 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.
Fri 11/215:30 amPDX - EYW
1 stop7h 59mAmerican Airlines
Tue 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.
Mon 9/2910:05 pmPDX - EYW
1 stop9h 50mDelta
Mon 10/61:57 pmEYW - PDX
1 stop11h 11mDelta
Deal found 9/13$557

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 September 15, 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

Tue 9/30

6:00 am-5:15 pm

1 stop8h 15m

Key West

Sat 10/4

11:50 am-6:58 pm

1 stop10h 08m

$465

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 10/20

5:34 am-4:13 pm

1 stop7h 39m

Key West

Thu 11/6

4:18 pm-11:31 pm

1 stop10h 13m

$475

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 10/13

10:10 pm-11:27 am

1 stop10h 17m

Key West

Mon 10/20

1:57 pm-10:08 pm

1 stop11h 11m

$511

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 10/16

11:59 pm-5:16 pm

2 stops14h 17m

Key West

Tue 10/21

2:32 pm-9:49 pm

1 stop10h 17m

$526

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 9/29

10:05 pm-10:55 am

1 stop9h 50m

Key West

Mon 10/6

1:57 pm-10:08 pm

1 stop11h 11m

$557

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 11/21

5:30 am-4:29 pm

1 stop7h 59m

Key West

Tue 11/25

4:10 pm-12:50 am

2 stops11h 40m

$557

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 10/25

12:43 pm-8:15 am

2 stops40h 32m

$168

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 10/18

12:43 pm-3:06 pm

2 stops47h 23m

$172

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 10/17

12:43 pm-2:40 pm

3 stops46h 57m

$179

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 10/17

3:53 pm-2:40 pm

2 stops43h 47m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 14 results
1
2

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 September 12, 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, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland 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.

How much does it cost to fly round-trip from Portland to Key West?

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 September 15, 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
8.0
Very good
7,954 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
8.0
Very good
7,954 reviews
Delta
8.0
Very good
7,954 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
8,929 reviews
Delta
8.0
Very good
7,954 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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
10,000 reviews
Delta
8.0
Very good
7,954 reviews

Overall

8.0

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

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 $475, Delta can have you in Key West from Portland in 7h 39m. 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 57% 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, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland 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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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$608FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$283Average$591FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$347Average$728FlexibilityNo cancel feeOn-time69%

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