$164 Cheap Flights from Key West (EYW) to Portland (PWM)

View $164 flight on Fri, Nov 7, 2025Opens in a new window

Popular airlines from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM)

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

Prices were available within the past 7 days and start at $164 for one-way flights and $269 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 29 - Sat, Nov 15
EYW
Key West
PWM
Portland
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 29 from Key West to Portland, returning Sat, Nov 15, priced at $269 found 2 days ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
EYW
Key West
PWM
Portland
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 27 from Key West to Portland, returning Sat, Jan 31, priced at $269 found 2 days ago
Delta
Sat, Nov 1 - Sat, Nov 15
EYW
Key West
PWM
Portland
$274 Roundtrip, found 2 days ago
$274
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 1 from Key West to Portland, returning Sat, Nov 15, priced at $274 found 2 days ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
EYW
Key West
PWM
Portland
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 27 from Key West to Portland, returning Sat, Jan 31, priced at $276 found 2 days ago
American Airlines
Fri, Oct 31 - Tue, Nov 4
EYW
Key West
PWM
Portland
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Oct 31 from Key West to Portland, returning Tue, Nov 4, priced at $279 found 2 days ago
Delta
Sat, Nov 22 - Sun, Dec 7
EYW
Key West
PWM
Portland
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Nov 22 from Key West to Portland, returning Sun, Dec 7, priced at $294 found 2 days ago
American Airlines
Fri, Nov 7 - Sat, Nov 15
EYW
Key West
PWM
Portland
$301 Roundtrip, found 3 days ago
$301
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 7 from Key West to Portland, returning Sat, Nov 15, priced at $301 found 3 days ago
American Airlines
Fri, Oct 17 - Mon, Oct 20
EYW
Key West
PWM
Portland
$304 Roundtrip, found 2 days ago
$304
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Oct 17 from Key West to Portland, returning Mon, Oct 20, priced at $304 found 2 days ago
American Airlines
Tue, Jan 27 - Sat, Jan 31
EYW
Key West
PWM
Portland
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Jan 27 from Key West to Portland, returning Sat, Jan 31, priced at $309 found 2 days ago
United
Fri, Oct 31 - Tue, Nov 4
EYW
Key West
PWM
Portland
$318 Roundtrip, found 2 days ago
$318
Roundtrip
found 2 days ago
Select United flight, departing Fri, Oct 31 from Key West to Portland, returning Tue, Nov 4, priced at $318 found 2 days ago

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

September is typically the cheapest month to fly

From $268 - $467 per traveler.

Frequently asked questions

How much does a flight from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM) cost?
Secure a cheap one-way flight from $164 or cheap return flight from $269 from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM)?
October is the most affordable month to fly from EYW to PWM. Traveling during quieter months is often the key to finding a great deal.
What is the cheapest airline that flies from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll fly you from EYW to PWM. Then, sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM)?
Direct flights from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your dates and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from EYW to PWM?
Generally you'll find the largest variety of flight choices on a Friday. Tuesdays tend to be the quietest.* However, this can vary based on the time of year, airline and other factors.*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. Jetport Airport (PWM)?
To avoid potential delays on the Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM) route, aim to travel before 3 PM. Departures after this hour are 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. Jetport Airport (PWM) last-minute?
Booking your plane ticket from EYW to PWM right before your getaway is usually more expensive. However, if there's some wiggle room with your schedule, you could bag a cheap last-minute fare.
Is it cheaper to book an EYW to PWM flight and hotel package?
You'll typically save money by securing an EYW to PWM 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 everything in one place. Once you've chosen your ideal accommodations and flights, consider adding extras including tours, activities and car rentals.
Can I cancel or change the date of my flight from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM)?
Generally, it's possible to cancel or reschedule your EYW to PWM flight. However, if the booking was made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Key West Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
American Airlines, Delta, United
Roundtrip price
$268
Distance
1469 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 October. 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 $164 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.