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$316+ Cheap flights from Key West to Portland (EYW - PDX)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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Cheap flight deals from Key West to Portland

Cheapest flights from Key West to Portland
Explore the most affordable flight options available from Key West to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 6, 2026.

This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/291:01 pm
EYW
-
PDX
1 stop10h 46m
American Airlines
Fri 6/55:49 am
PDX
-
EYW
1 stop10h 00m
American Airlines
Deal found 5/5$369
This Kiwi.com deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2011:46 am
EYW
-
PDX
2 stops29h 08m
Multiple Airlines
Sun 5/242:44 pm
PDX
-
EYW
1 stop17h 18m
Multiple Airlines
Deal found 5/5$421
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
EYW
-
PDX
1 stop9h 06m
Delta
Wed 9/165:30 am
PDX
-
EYW
2 stops11h 15m
Delta
Deal found 5/3$449
This American Airlines deal was found by Cheapflights users on 5/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/82:21 pm
EYW
-
PDX
1 stop10h 08m
American Airlines
Sun 7/1210:30 pm
PDX
-
EYW
1 stop12h 10m
American Airlines
Deal found 5/4$457
This Delta deal was found by Cheapflights users on 5/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/141:22 pm
EYW
-
PDX
1 stop8h 16m
Delta
Sat 5/239:39 pm
PDX
-
EYW
1 stop10h 14m
Delta
Deal found 5/3$459
This American Airlines deal was found by Cheapflights users on 5/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:50 pm
EYW
-
PDX
1 stop8h 58m
American Airlines
Wed 9/165:20 am
PDX
-
EYW
2 stops10h 07m
American Airlines
Deal found 5/5$462

Find flight deals from Key West to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$369
(American Airlines)

One-way from

$316
(Kiwi.com)
Provider with most accurate pricing for Key West-Portland flight deals.
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Provider most trusted by Cheapflights users for Key West-Portland flights.
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From Key West to Portland
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One-way flight from Key West to Portland
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 6, 2026.
Use the filters below to find and compare flights from Key West to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 5/29

1:01 pm-8:47 pm

1 stop10h 46m

Portland

Fri 6/5

5:49 am-6:49 pm

1 stop10h 00m

$369

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 7/8

2:21 pm-9:29 pm

1 stop10h 08m

Portland

Sun 7/12

10:30 pm-1:40 pm

1 stop12h 10m

$457

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 9/2

1:49 pm-11:07 pm

2 stops12h 18m

Portland

Wed 9/16

5:20 am-6:27 pm

2 stops10h 07m

$467

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 5/20

3:58 pm-11:53 pm

1 stop10h 55m

Portland

Sun 5/24

5:49 am-6:49 pm

1 stop10h 00m

$484
Quickest round-trip

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 9/1

2:20 pm-10:03 pm

1 stop10h 43m

Portland

Sat 9/5

10:45 am-10:11 pm

1 stop8h 26m

$667
Cheapest one-way

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 7/26

8:48 pm-6:04 pm

3 stops24h 16m

$316

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 7/26

4:21 pm-10:36 am

1 stop21h 15m

$449

Key WestPortland

EYW - PDX

EYWPDX

Key West

Mon 5/18

1:22 pm-11:55 pm

2 stops13h 33m

$503
Quickest one-way

Key WestPortland

EYW - PDX

EYWPDX

Key West

Mon 5/18

3:58 pm-11:54 pm

2 stops10h 56m

$1,108

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/4

Sorted by cheapest first
  • Most accurate provider: When it comes to deals on Key West-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Portland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Key West-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Key West-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Key West to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Key West with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Key West to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Key West to Portland?

    Departing from Key West to Portland will take you 10h 46m. Airlines will cover a distance of 2685 mi.

  • Can I find deals for flights from Key West to Portland that include hotel bookings?

    Yes. In addition to deals on Key West to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Portland.

  • Can I find deals for business class flights from Key West to Portland?

    Yes. Cheapflights offers flight deals from Key West to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Beaverton
Seaside
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Pacific City

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