$163 Cheap flight deals from Portland (PDX) to Key West (EYW)

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This Weekend's Flight Deals from Portland to Key West

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, May 3 - Wed, May 7
PDX
Portland Intl.
EYW
Key West Intl.
$698 Roundtrip, found 5 days ago
$698
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, May 3 from Portland Intl. to Key West Intl., returning Wed, May 7, priced at $698 found 5 days ago

Airfares from $163 One Way, $365 Round Trip from Portland to Key West

Prices starting at $365 for return flights and $163 for one-way flights to Key West were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 8 - Wed, Jul 16
PDX
Portland
EYW
Key West
$365 Roundtrip, found 1 day ago
$365
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 8 from Portland to Key West, returning Wed, Jul 16, priced at $365 found 1 day ago
Sat, Jul 12 - Wed, Jul 16
PDX
Portland
EYW
Key West
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jul 12 from Portland to Key West, returning Wed, Jul 16, priced at $406 found 1 day ago
Tue, Jul 8 - Tue, Jul 15
PDX
Portland
EYW
Key West
$411 Roundtrip, found 1 day ago
$411
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 8 from Portland to Key West, returning Tue, Jul 15, priced at $411 found 1 day ago
Tue, Jul 8 - Thu, Jul 17
PDX
Portland
EYW
Key West
$461 Roundtrip, found 1 day ago
$461
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 8 from Portland to Key West, returning Thu, Jul 17, priced at $461 found 1 day ago
Wed, Jul 9 - Tue, Jul 15
PDX
Portland
EYW
Key West
$465 Roundtrip, found 1 day ago
$465
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 9 from Portland to Key West, returning Tue, Jul 15, priced at $465 found 1 day ago

Key West economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West
4.0-star property

The Perry Hotel & Marina Key West

9.4/10 Exceptional! (1,010 reviews)

Jun 19 - Jun 22

3 night stay

Portland (PDX) to Key West (EYW)

United • Non-stop • Coach

Key West (EYW) to Portland (PDX)

Sun Country Airlines • Non-stop • Coach
per person
found 1 day ago
Excellent facility. The on site personnel were fabulous and the shuttle service is more than adequate.

Reviewed on Jan 5, 2025

Oceans Edge Key West Resort, Hotel & Marina
4.0-star property

Oceans Edge Key West Resort, Hotel & Marina

8.8/10 Excellent! (1,623 reviews)

Jun 19 - Jun 22

3 night stay

Portland (PDX) to Key West (EYW)

United • Non-stop • Coach

Key West (EYW) to Portland (PDX)

Sun Country Airlines • Non-stop • Coach
per person
found 1 day ago
Beauty Property. Excellent Staff

Reviewed on Dec 14, 2024

Southernmost Beach Resort
4.0-star property

Southernmost Beach Resort

8.6/10 Excellent! (2,353 reviews)

Jun 19 - Jun 22

3 night stay

Portland (PDX) to Key West (EYW)

United • Non-stop • Coach

Key West (EYW) to Portland (PDX)

Sun Country Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
I really enjoyed my long weekend at the Southernmost Beach Resort. There are several pools, beaches, bars and a restaurant. My room was clean and spacious. All the staff I encountered were super friendly. Great location and easy walking distance to Duval.

Reviewed on Apr 1, 2025

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More About Flying To Key West from Portland

Route Information for Flights from Portland to Key West

Origin Airport IATA Code
PDX
Destination Airport IATA Code
EYW
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Portland to Key West

Finding cheap flights from Portland to Key West need never be a problem again when you put your faith in Orbitz, the online leader in discounted travel arrangements. You’ll get guaranteed low prices every time you book and be able to choose from a great selection of hotels, flight, cruises, and more.

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Frequently asked questions

Am I able to catch a flight from Portland to Key West now?
Go right to our Covid-19 Travel Advisor for the most comprehensive information on quarantine requirements and travel restrictions when catching a flight from Portland to Key West.
What is the shortest flight from Portland to Key West?
From Portland, the thrilling sights and sounds of Key West are at least 6 hours and 19 minutes away. Lock in your favorite seat, or maybe even upgrade to one with extra legroom, and get to your destination in total comfort.
If I am not able to travel due to COVID-19, can I cancel my flight to Key West?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Key West have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Key West with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Key West without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2020 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data the cheapest month to fly is August. Perfect for those who need a weekend getaway, or just a break from it all before the weather changes. Be aware that the most expensive time to fly is the height of summer, with ticket prices peaking in the month of June.
How can I save money on flights?
To really save big on your next vacation, think outside the box. Select two different airlines or fare types for your return trip and you’ll generally get a much better deal. Those who tried this on Orbitz in 2020 saved up to 45% on their airfares. Get mixing and matching today!

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.