$184 Cheap Flights from Portland (PWM) to Key West (EYW)

View $184 flight on Mon, Jan 12, 2026Opens in a new window

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

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

Prices were available within the past 7 days and start at $184 for one-way flights and $259 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Jan 20 - Tue, Jan 27
PWM
Portland
EYW
Key West
$259 Roundtrip, found 9 hours ago
$259
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Jan 20 from Portland to Key West, returning Tue, Jan 27, priced at $259 found 9 hours ago
Delta
Tue, Feb 3 - Sun, Feb 8
PWM
Portland
EYW
Key West
$264 Roundtrip, found 22 hours ago
$264
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Feb 3 from Portland to Key West, returning Sun, Feb 8, priced at $264 found 22 hours ago
Delta
Tue, Feb 3 - Wed, Feb 11
PWM
Portland
EYW
Key West
$264 Roundtrip, found 22 hours ago
$264
Roundtrip
found 22 hours ago
Select Delta flight, departing Tue, Feb 3 from Portland to Key West, returning Wed, Feb 11, priced at $264 found 22 hours ago
United
Sat, Sep 19 - Sat, Sep 26
PWM
Portland
EYW
Key West
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select United flight, departing Sat, Sep 19 from Portland to Key West, returning Sat, Sep 26, priced at $269 found 2 days ago
Delta
Fri, Feb 6 - Wed, Feb 11
PWM
Portland
EYW
Key West
$269 Roundtrip, found 22 hours ago
$269
Roundtrip
found 22 hours ago
Select Delta flight, departing Fri, Feb 6 from Portland to Key West, returning Wed, Feb 11, priced at $269 found 22 hours ago
American Airlines
Tue, Feb 17 - Tue, Feb 24
PWM
Portland
EYW
Key West
$271 Roundtrip, found 18 hours ago
$271
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Feb 17 from Portland to Key West, returning Tue, Feb 24, priced at $271 found 18 hours ago
American Airlines
Sat, Jan 31 - Wed, Feb 4
PWM
Portland
EYW
Key West
$276 Roundtrip, found 1 day ago
$276
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jan 31 from Portland to Key West, returning Wed, Feb 4, priced at $276 found 1 day ago
American Airlines
Wed, Jan 28 - Tue, Feb 3
PWM
Portland
EYW
Key West
$276 Roundtrip, found 2 days ago
$276
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Jan 28 from Portland to Key West, returning Tue, Feb 3, priced at $276 found 2 days ago
American Airlines
Sat, Dec 6 - Tue, Dec 9
PWM
Portland
EYW
Key West
$279 Roundtrip, found 14 hours ago
$279
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Sat, Dec 6 from Portland to Key West, returning Tue, Dec 9, priced at $279 found 14 hours ago
JetBlue Airways
Sun, Mar 29 - Tue, Apr 7
PWM
Portland
EYW
Key West
$535 Roundtrip, found 1 day ago
$535
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Mar 29 from Portland to Key West, returning Tue, Apr 7, priced at $535 found 1 day ago

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

September is typically the cheapest month to fly

From $268 - $423 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 $367
EYW
Key West Intl.
CheapestClosest
Average driving time to city center8 min
Flights from $367

Frequently asked questions

How much does a flight from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW) cost?
Grab a cheap one-way flight from $184 or cheap return flight from $259 from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW) 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 Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW)?
Planning your trip for January is a great way to save, as it's the cheapest month for flights between PWM and EYW. You'll typically find the lowest prices during the off-season.
What is the cheapest airline that flies from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW)?
Expedia's filter tool lets you easily compare different airlines, flight durations and fares all in one place. Customize the search to your preferences, then sort by "Price (lowest to highest)" to find out which carrier offers the cheapest PWM to EYW flight.
How many flights per day from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW)?
You'll need to take a flight with a layover when traveling from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW). There are no daily direct flights on this route. However, just filter your search to include one or more stops to discover an option that works for you.
What day of the week has the most flights from PWM to EYW?
Usually you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the season, carrier 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 Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW)?
To reach Key West Intl. Airport (EYW) on schedule, pick a flight that leaves from Portland Intl. Jetport Airport (PWM) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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. Jetport Airport (PWM) to Key West Intl. Airport (EYW) last-minute?
Holding off until just before your trip to book your flight from PWM to EYW often results in higher prices. While it's possible to find some last-minute discounts, they aren't always guaranteed. Keep your travel plans flexible to boost your chances of getting a bargain.
Is it cheaper to book a PWM to EYW flight and hotel package?
You'll generally save money by securing a PWM 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 everything in one convenient place. After selecting your ideal accommodations and flights, you can add extras like activities, car rentals and tours.
Can I cancel or change the date of my flight from Portland Intl. Jetport Airport (PWM) to Key West Intl. Airport (EYW)?
If you booked your PWM to EYW flight in the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare 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

Origin airport
Portland Intl. Jetport
Destination airport
Key West Intl.
Airlines serving
American Airlines, Delta, JetBlue Airways, United
Roundtrip price
$258
Distance
1469 mi

Book with confidence

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 January. 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 $184 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.

 

Portland to Key West Flights

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*Available to One Key members.