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 8h 56m. 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.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Delta is priced at 62% lower than the current average price of a flight leaving 3 months from now.

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

What are the most popular airlines that fly from Portland to Key West?

When booking a flight from Portland to Key West, you may want to consider flying on American Airlines, Delta or United Airlines as they are the most popular for this route.

What is the cheapest time of day to fly from PDX to EYW?

When flying from Portland 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.

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.

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.

$223+ Flights from Portland to Key West

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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 December 31, 2025.

Mon 12/2911:55 pmPDX - EYW

1 stop9h 39mUnited Airlines

Thu 1/86:05 pmEYW - PDX

2 stops18h 40mUnited Airlines

Deal found 12/28

$822

Best flights from Portland to Key West
Discover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 31, 2025.

Thu 1/2211:01 pmPDX - EYW

1 stop8h 56mAmerican Airlines

Mon 1/264:37 pmEYW - PDX

1 stop10h 09mAmerican Airlines

Deal found 12/30

$329

Thu 1/2911:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Thu 2/54:15 pmEYW - PDX

1 stop9h 17mUnited Airlines

Deal found 12/30

$402

Wed 1/216:00 amPDX - EYW

1 stop7h 24mAmerican Airlines

Thu 1/291:22 pmEYW - PDX

1 stop10h 02mAmerican Airlines

Deal found 12/29

$329

Fri 1/2311:01 pmPDX - EYW

1 stop9h 04mAmerican Airlines

Mon 1/264:37 pmEYW - PDX

1 stop10h 09mAmerican Airlines

Deal found 12/29

$329

Fri 2/67:38 amPDX - EYW

2 stops13h 18mAmerican Airlines

Wed 2/111:33 pmEYW - PDX

2 stops12h 25mAmerican Airlines

Deal found 12/29

$339

Wed 2/116:00 amPDX - EYW

2 stops12h 47mAmerican Airlines

Tue 2/1712:55 pmEYW - PDX

1 stop10h 49mAmerican Airlines

Deal found 12/29

$359

Sat 4/116:00 amPDX - EYW

1 stop8h 02mAmerican Airlines

Sat 4/182:29 pmEYW - PDX

1 stop11h 20mAmerican Airlines

Deal found 12/29

$417

Last-minute flights from Portland to Key West
Discover last-minute flight deals from Portland to Key West. Data last updated December 31, 2025 and is based on user searches.

Tue 1/610:15 pmPDX - EYW

2 stops11h 48mAmerican Airlines

Tue 1/134:37 pmEYW - PDX

1 stop10h 09mAmerican Airlines

Deal found 12/30

$444

Tue 1/136:50 amPDX - EYW

1 stop9h 50mDelta

Sat 1/177:10 amEYW - PDX

2 stops12h 16mDelta

Deal found 12/29

$414

Tue 1/1311:01 pmPDX - EYW

1 stop8h 56mAmerican Airlines

Sat 1/174:37 pmEYW - PDX

1 stop10h 09mAmerican Airlines

Deal found 12/29

$447

Wed 1/216:00 amPDX - EYW

1 stop7h 24mAmerican Airlines

Thu 1/291:22 pmEYW - PDX

1 stop10h 02mAmerican Airlines

Deal found 12/29

$329

Thu 1/226:00 amPDX - EYW

2 stops12h 47mAmerican Airlines

Mon 1/264:37 pmEYW - PDX

1 stop10h 09mAmerican Airlines

Deal found 12/30

$334

Mon 1/2611:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Mon 2/24:15 pmEYW - PDX

1 stop9h 17mUnited Airlines

Deal found 12/29

$428

Thu 1/2911:05 pmPDX - EYW

1 stop10h 58mUnited Airlines

Thu 2/54:15 pmEYW - PDX

1 stop9h 17mUnited Airlines

Deal found 12/30

$402

One-way flights from Portland to Key West
Search for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated December 31, 2025.

Thu 2/196:58 pmPDX - EYW

3 stops59h 08mMultiple Airlines

Deal found 12/29

$223

Thu 2/1910:38 pmPDX - EYW

1 stop11h 37mUnited Airlines

Deal found 12/29

$353

Thu 2/199:44 pmPDX - EYW

2 stops12h 31mAmerican Airlines

Deal found 12/29

$358

Wed 5/1311:59 pmPDX - EYW

1 stop15h 16mAmerican Airlines

Deal found 12/30

$362

Wed 5/139:46 pmPDX - EYW

3 stops36h 44mMultiple Airlines

Deal found 12/30

$458

Wed 3/1811:59 pmPDX - EYW

1 stop9h 55mAmerican Airlines

Deal found 12/30

$864

Wed 3/181:00 pmPDX - EYW

3 stops24h 36mUnited Airlines

Deal found 12/30

$1,468

Find flight deals from Portland to Key West

Most accurate provider	eDreams 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$329 (American Airlines)
One-way from	$223 (Kiwi.com)
Popular in	June
Cheapest in	September
Average price	$616

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 ($30 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in December 2025

Search Deals

Fly from

Fly to

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 1/22

11:01 pm-10:57 am

1 stop8h 56m

Key West

Mon 1/26

4:37 pm-11:46 pm

1 stop10h 09m

$329

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 1/21

6:00 am-4:24 pm

1 stop7h 24m

Key West

Thu 1/29

1:22 pm-8:24 pm

1 stop10h 02m

$329

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 1/23

11:01 pm-11:05 am

1 stop9h 04m

Key West

Mon 1/26

4:37 pm-11:46 pm

1 stop10h 09m

$329

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 2/6

7:38 am-11:56 pm

2 stops13h 18m

Key West

Wed 2/11

1:33 pm-10:58 pm

2 stops12h 25m

$339

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 2/11

6:00 am-9:47 pm

2 stops12h 47m

Key West

Tue 2/17

12:55 pm-8:44 pm

1 stop10h 49m

$359

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 1/29

11:05 pm-1:03 pm

1 stop10h 58m

Key West

Thu 2/5

4:15 pm-10:32 pm

1 stop9h 17m

$402

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 4/11

6:00 am-5:02 pm

1 stop8h 02m

Key West

Sat 4/18

2:29 pm-10:49 pm

1 stop11h 20m

$417

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 2/19

6:58 pm-9:06 am

3 stops59h 08m

$223

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 2/19

10:38 pm-1:15 pm

1 stop11h 37m

$353

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 5/13

8:00 am-10:36 pm

2 stops11h 36m

$358

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 14 results

Compare providers for flights from Portland to Key West

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 December.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy2 stars	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*1 star
eDreams	Price Accuracy3 stars	Trust 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?

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

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

8,013 reviews

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

8,013 reviews

Delta

7.9

Good

8,013 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

United Airlines

7.4

Good

9,124 reviews

Delta

7.9

Good

8,013 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

American Airlines

7.2

Good

11,074 reviews

Delta

7.9

Good

8,013 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

Related info for your journey

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 8h 56m. 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.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Delta is priced at 62% 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

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Other flights to Key West

Top 3 airlines flying from Portland to Key West

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$261	Average$608	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$308	Average$591	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$333	Average$622	FlexibilityNo cancel fee	On-time69%

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$223+ 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 2/19. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Portland to Key West with Cheapflights

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3. Compare prices and book

Cheap flight deals from Portland to Key West

Cheapest flights from Portland to Key WestExplore 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 December 31, 2025.

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 December 31, 2025.

Find flight deals from Portland to Key West

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Key West that are best for you.

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 December.

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.

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?

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

Reviews of airlines servicing Key West

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.

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?

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

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

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

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

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

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.

Alternative routes for Portland to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Portland to Key West

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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 December 31, 2025.