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$197+ 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 6/19. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
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 March 11, 2026.

This American Airlines deal was found by Cheapflights users on 3/6. 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.
Thu 5/143:58 pm
EYW
-
PDX
1 stop10h 55m
American Airlines
Sat 5/2310:59 pm
PDX
-
EYW
2 stops14h 08m
American Airlines
Deal found 3/6$374
This American Airlines deal was found by Cheapflights users on 3/10. 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 3/253:56 pm
EYW
-
PDX
1 stop10h 48m
American Airlines
Sun 3/295:40 am
PDX
-
EYW
1 stop7h 44m
American Airlines
Deal found 3/10$429
This United Airlines deal was found by Cheapflights users on 3/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:47 pm
EYW
-
PDX
1 stop9h 12m
United Airlines
Tue 5/510:15 pm
PDX
-
EYW
1 stop12h 30m
United Airlines
Deal found 3/8$449
This American Airlines deal was found by Cheapflights users on 3/8. 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.
Sat 4/44:20 pm
EYW
-
PDX
1 stop11h 02m
American Airlines
Mon 4/1310:23 pm
PDX
-
EYW
1 stop9h 53m
American Airlines
Deal found 3/8$468
This United Airlines deal was found by Cheapflights users on 3/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/153:52 pm
EYW
-
PDX
1 stop9h 42m
United Airlines
Sat 4/1811:15 pm
PDX
-
EYW
1 stop11h 16m
United Airlines
Deal found 3/9$499

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 March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$374
(American Airlines)

One-way from

$197
(Kiwi.com)
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Portland flights.
Search Deals
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 March 11, 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

Thu 5/14

3:58 pm-11:53 pm

1 stop10h 55m

Portland

Sat 5/23

10:59 pm-4:07 pm

2 stops14h 08m

$374
Quickest round-trip

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 3/25

3:56 pm-11:44 pm

1 stop10h 48m

Portland

Sun 3/29

5:40 am-4:24 pm

1 stop7h 44m

$429

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 5/1

4:47 pm-10:59 pm

1 stop9h 12m

Portland

Tue 5/5

10:15 pm-1:45 pm

1 stop12h 30m

$449
Cheapest one-way

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 6/19

1:11 pm-9:09 pm

3 stops34h 58m

$295

Key WestPortland

EYW - PDX

EYWPDX

Key West

Mon 6/15

1:11 pm-11:13 am

3 stops49h 02m

$322
Quickest one-way

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 6/19

4:37 pm-11:59 pm

1 stop10h 22m

$363

Key WestPortland

EYW - PDX

EYWPDX

Key West

Mon 6/15

4:19 pm-11:56 pm

1 stop10h 37m

$418

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/6

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.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated March 11, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Portland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,419 reviews

Comfort

7.2

Food

6.4

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,419 reviews
American Airlines
7.1
Good
11,419 reviews

Comfort

7.2

Food

6.4

Overall

7.1

Boarding

7.5

Entertainment

6.9

Crew

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

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 55m. Airlines will cover a distance of 2685 mi.

  • What is the cheapest airline to fly from Key West to Portland round-trip?

    Cheapflights users have booked flights from Key West to Portland round-trip from $344.

  • 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
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Beaverton
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Astoria

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Key West to Portland

Discover the top airline that operate flights from Key West to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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