$188 Cheap Flights from Portland (PDX) to Key West (EYW)

View $188 flight on Wed, Feb 18, 2026Opens in a new window

Popular airlines from Portland International Airport (PDX) to Key West Intl. Airport (EYW)

Cheap Flights from Portland to Key West (PDX-EYW)

Prices were available within the past 7 days and start at $188 for one-way flights and $335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, May 24 - Sat, May 30
PDX
Portland
EYW
Key West
$335 Roundtrip, found 10 hours ago
$335
Roundtrip
found 10 hours ago
Select United flight, departing Sun, May 24 from Portland to Key West, returning Sat, May 30, priced at $335 found 10 hours ago
American Airlines
Wed, Jan 21 - Tue, Jan 27
PDX
Portland
EYW
Key West
$365 Roundtrip, found 5 days ago
$365
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jan 21 from Portland to Key West, returning Tue, Jan 27, priced at $365 found 5 days ago
United
Mon, Jan 26 - Mon, Feb 2
PDX
Portland
EYW
Key West
$384 Roundtrip, found 3 days ago
$384
Roundtrip
found 3 days ago
Select United flight, departing Mon, Jan 26 from Portland to Key West, returning Mon, Feb 2, priced at $384 found 3 days ago
Delta
Tue, Jan 27 - Tue, Feb 10
PDX
Portland
EYW
Key West
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jan 27 from Portland to Key West, returning Tue, Feb 10, priced at $389 found 1 day ago
Delta
Tue, Nov 4 - Fri, Nov 14
PDX
Portland
EYW
Key West
$390 Roundtrip, found 5 days ago
$390
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 4 from Portland to Key West, returning Fri, Nov 14, priced at $390 found 5 days ago
American Airlines
Wed, Jan 21 - Tue, Jan 27
PDX
Portland
EYW
Key West
$391 Roundtrip, found 5 days ago
$391
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jan 21 from Portland to Key West, returning Tue, Jan 27, priced at $391 found 5 days ago
American Airlines
Tue, Nov 4 - Sat, Nov 15
PDX
Portland
EYW
Key West
$394 Roundtrip, found 4 hours ago
$394
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Tue, Nov 4 from Portland to Key West, returning Sat, Nov 15, priced at $394 found 4 hours ago
American Airlines
Wed, Jan 21 - Tue, Jan 27
PDX
Portland
EYW
Key West
$396 Roundtrip, found 5 days ago
$396
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jan 21 from Portland to Key West, returning Tue, Jan 27, priced at $396 found 5 days ago
Delta
Fri, Oct 31 - Tue, Nov 4
PDX
Portland
EYW
Key West
$399 Roundtrip, just found
$399
Roundtrip
just found
Select Delta flight, departing Fri, Oct 31 from Portland to Key West, returning Tue, Nov 4, priced at $399 just found
Alaska Airlines
Sat, Nov 8 - Sat, Nov 15
PDX
Portland
EYW
Key West
$693 Roundtrip, found 2 days ago
$693
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Nov 8 from Portland to Key West, returning Sat, Nov 15, priced at $693 found 2 days ago

Find the cheapest month to fly from Portland (PDX) to Key West (EYW)

September is typically the cheapest month to fly

From $278 - $795 per traveler.

Alternative airports near Key West

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Key West Intl. EYW. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $450
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $450
Flights from Portland (PDX) to Key West (EYW)
Origin airport
Portland Intl.
Destination airport
Key West Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, United
Roundtrip price
$334
Distance
2686 mi

Portland to Key West Flights

The cheapest times to fly from Portland to Key West

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Portland to Key West are during the month of May. You can find some of the cheapest flights from Portland to Key West with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Portland to Key West

Sunday is one of the best days to book for cheap flights from Portland to Key West: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Portland to Key West

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Portland to Key West in 2025. You can also book with separate airlines for your outbound and return journeys, from $188 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Portland to Key West flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Portland to Key West airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW) cost?
Grab a cheap one-way flight from $188 or cheap return flight from $335 from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW)?
May is the least expensive month to fly from PDX to EYW. Planning your trip for the off-season is often the key to finding better deals on flights.
What is the cheapest airline that flies from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest PDX to EYW flight.
How many flights per day from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW)?
There are no daily direct flights available from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW). But you can book flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be on your way in no time at all.
What day of the week has the most flights from PDX to EYW?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can vary based on a number of factors, including the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW)?
To avoid possible delays on the Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW) route, aim to travel before 3 PM. Departures after this hour have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW) last-minute?
Waiting until just before your trip to book a flight from PDX to EYW generally means paying more. While you may find some last-minute deals, they aren't always guaranteed. Be flexible with your travel plans for the best chance of snagging a bargain.
Is it cheaper to book a PDX to EYW flight and hotel package?
You'll generally save money by securing a PDX to EYW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've chosen your ideal accommodations and flights, consider adding extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Portland Intl. Airport (PDX) to Key West Intl. Airport (EYW)?
In most cases, you're able to reschedule or cancel your PDX to EYW flight. However, additional fees may apply, especially if you made your booking more than 24 hours ago. Check your itinerary for the airline's policies and fees on flight changes, or if you'd like more details, go to our Customer Service portal.

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*Available to One Key members.