$202 Cheap Flights from Key West (EYW) to Portland (PDX)

View $202 flight on Wed, Feb 18, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $202 for one-way flights and $365 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Jan 7 - Wed, Jan 14
EYW
Key West
PDX
Portland
$365 Roundtrip, found 4 days ago
$365
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jan 7 from Key West to Portland, returning Wed, Jan 14, priced at $365 found 4 days ago
American Airlines
Tue, Feb 10 - Wed, Feb 18
EYW
Key West
PDX
Portland
$376 Roundtrip, found 18 hours ago
$376
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Feb 10 from Key West to Portland, returning Wed, Feb 18, priced at $376 found 18 hours ago
American Airlines
Tue, Feb 10 - Wed, Feb 18
EYW
Key West
PDX
Portland
$381 Roundtrip, found 18 hours ago
$381
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Feb 10 from Key West to Portland, returning Wed, Feb 18, priced at $381 found 18 hours ago
United
Thu, Oct 30 - Mon, Nov 3
EYW
Key West
PDX
Portland
$384 Roundtrip, found 3 hours ago
$384
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Oct 30 from Key West to Portland, returning Mon, Nov 3, priced at $384 found 3 hours ago
Delta
Wed, Feb 11 - Tue, Feb 17
EYW
Key West
PDX
Portland
$389 Roundtrip, found 18 hours ago
$389
Roundtrip
found 18 hours ago
Select Delta flight, departing Wed, Feb 11 from Key West to Portland, returning Tue, Feb 17, priced at $389 found 18 hours ago
American Airlines
Wed, Jan 7 - Wed, Jan 14
EYW
Key West
PDX
Portland
$391 Roundtrip, found 4 days ago
$391
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jan 7 from Key West to Portland, returning Wed, Jan 14, priced at $391 found 4 days ago
American Airlines
Tue, Feb 10 - Wed, Feb 18
EYW
Key West
PDX
Portland
$394 Roundtrip, found 18 hours ago
$394
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Feb 10 from Key West to Portland, returning Wed, Feb 18, priced at $394 found 18 hours ago
American Airlines
Wed, Jan 7 - Wed, Jan 14
EYW
Key West
PDX
Portland
$396 Roundtrip, found 4 days ago
$396
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Jan 7 from Key West to Portland, returning Wed, Jan 14, priced at $396 found 4 days ago
American Airlines
Tue, Feb 10 - Wed, Feb 18
EYW
Key West
PDX
Portland
$399 Roundtrip, found 18 hours ago
$399
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Feb 10 from Key West to Portland, returning Wed, Feb 18, priced at $399 found 18 hours ago
Delta
Fri, Oct 31 - Tue, Nov 4
EYW
Key West
PDX
Portland
$402 Roundtrip, found 5 days ago
$402
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Oct 31 from Key West to Portland, returning Tue, Nov 4, priced at $402 found 5 days ago

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

May is typically the cheapest month to fly

From $278 - $1,041 per traveler.

Frequently asked questions

How much does a flight from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX) cost?
Secure a cheap one-way flight from $202 or cheap return flight from $365 from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX)?
January is the least expensive month to fly from EYW to PDX. Timing your trip outside of the busy season is often the key to finding better fares.
What is the cheapest airline that flies from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX)?
To find the cheapest airline flying from EYW to PDX, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and seat class. You can then sort your results by "Price (lowest to highest)" to see the cheapest flights first.
How many flights per day from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX)?
There are no daily direct flights available from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX). But you can opt for flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds before you know it.
What day of the week has the most flights from EYW to PDX?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX)?
Choose a flight from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX) that takes off before 3 PM to reduce the likelihood of delays. Later departures are on average 22% more likely to be 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 Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX) last-minute?
Last-minute fares from EYW to PDX are typically more expensive. To lock in the best rates, start searching for flights as early as possible. That being said, if your travel plans are flexible, it's possible to find a cheap ticket just before your departure.
Is it cheaper to book an EYW to PDX flight and hotel package?
Securing an EYW to PDX flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your travels all in one place. Choose from our impressive range of accommodations and then add car rentals, flights and activities to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Key West Intl. Airport (EYW) to Portland Intl. Airport (PDX)?
If you reserved your EYW to PDX flight within the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the ticket type you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, visit our Customer Service portal for more information.

Travel information

Travel information

Origin airport
Key West Intl.
Destination airport
Portland Intl.
Airlines serving
American Airlines, Delta, United
Roundtrip price
$364
Distance
2686 mi

Book with confidence

Book with confidence

Key West to Portland Flights

The cheapest times to fly from Key West to Portland

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 Key West to Portland are during the month of January. You can find some of the cheapest flights from Key West to Portland with Expedia's search tool and vast selection of airlines.

 

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

Sunday is one of the best days to book for cheap flights from Key West to Portland: 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 Key West to Portland

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 Key West to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $202 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 Key West to Portland 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 Key West to Portland 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.

 

Key West to Portland Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.