£380 Cheap Flights from Portland (PDX) to Key West (EYW)

View £380 flight on Fri, 15 May 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at £380 for one-way flights and £504 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£504 Return, found 8 hours ago
£504
Return
found 8 hours ago
Select American Airlines flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £504 found 8 hours ago
Delta
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£504 Return, found 8 hours ago
£504
Return
found 8 hours ago
Select Delta flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £504 found 8 hours ago
American Airlines
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£519 Return, found 8 hours ago
£519
Return
found 8 hours ago
Select American Airlines flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £519 found 8 hours ago
Delta
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£528 Return, found 8 hours ago
£528
Return
found 8 hours ago
Select Delta flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £528 found 8 hours ago
American Airlines
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£545 Return, found 8 hours ago
£545
Return
found 8 hours ago
Select American Airlines flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £545 found 8 hours ago
American Airlines
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£560 Return, found 8 hours ago
£560
Return
found 8 hours ago
Select American Airlines flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £560 found 8 hours ago
Delta
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£586 Return, found 8 hours ago
£586
Return
found 8 hours ago
Select Delta flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £586 found 8 hours ago
American Airlines
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£601 Return, found 8 hours ago
£601
Return
found 8 hours ago
Select American Airlines flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £601 found 8 hours ago
Delta
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£609 Return, found 8 hours ago
£609
Return
found 8 hours ago
Select Delta flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £609 found 8 hours ago
United
Fri, 15 May - Fri, 22 May
PDX
Portland
EYW
Key West
£727 Return, found 8 hours ago
£727
Return
found 8 hours ago
Select United flight, departing Fri, 15 May from Portland to Key West, returning Fri, 22 May, priced at £727 found 8 hours ago

Frequently asked questions

How do I find cheap flights from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
To find a cheap flight from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
There are approximately 32 connecting flights per day from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.). Some common connection points include Seattle - Tacoma Intl. (SEA), O'Hare Intl. (ORD), and San Francisco Intl. (SFO).
What is the earliest flight from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
The earliest flight from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) typically departs at approximately 12:05 AM local time, operated by American Airlines. This is a seasonal service active in June. An early departure like this can help maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
You'll typically find the most flights from Portland Intl. (PDX) to Key West Intl. (EYW) on a Thursday, with around 22 flights available. This gives you plenty of options for your travel plans. Major airlines on this route include United Airlines, American Airlines, and Alaska Airlines. Looking at the weekly trends, Thursdays have notably more flight options compared to other days.
What are the most popular departure times for flights from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
The most popular departure times for flights from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) are in the late evening, from 9pm to midnight. About 43% of passengers prefer this time window. Many major carriers, including Delta Air Lines, American Airlines and United Airlines, offer flights during this window. These times work well because you can maximize your day in Portland before your evening flight, and you'll arrive in Key West ready to start your trip.
How long does it take to fly from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
A flight from PDX to EYW with a layover takes around 10 hours 20 minutes, with the route covering approximately 2,687 miles. Keep in mind that actual flight times can vary due to wind patterns, weather, and air traffic.
Can you fly business or first class from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
Select the "Business class" and "First class" filters when looking for PDX to EYW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) flight with Expedia?
It's easy to earn miles on a Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Key West from Portland Intl. (PDX)?
From Portland Intl. (PDX), you can fly into Key West Intl. (EYW) to reach Key West. Some flights may connect through major hubs like San Francisco Intl. (SFO), Los Angeles Intl. (LAX), Seattle - Tacoma Intl. (SEA) before reaching Key West. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) at the last minute?
Typically, booking a last minute flight from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) flight and hotel package?
Securing a Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.)?
If you booked your Portland, OR (PDX-Portland Intl.) to Key West, FL (EYW-Key West Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Portland Intl.
Destination airport
Key West Intl.
Return price
£504
Distance
4298 km

Book with confidence

Compare flights from Portland to Key West easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Portland to Key West. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Key West Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to Key West Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Portland Intl. (PDX) to Key West Intl. (EYW)

The easiest way to view the best deals on flights from Portland to Key West today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Portland Intl. to Key West Intl. start at just £504 and range up to £727.  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Portland and Key West
  • booking your flight during May, the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Portland to Key West flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Portland Intl. to Key West Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Compare flights from Portland to Key West easily and book with confidence

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*Available to Expedia members.