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$329+ Cheap flights from Key West to Portland (EYW - PDX)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Feb 19 — Feb 261
Thu 2/19
Thu 2/26
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 January 20, 2026.

This American Airlines deal was found by Cheapflights users on 1/18. 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 54m
American Airlines
Sat 5/2310:30 pm
PDX
-
EYW
1 stop12h 12m
American Airlines
Deal found 1/18$329
This American Airlines deal was found by Cheapflights users on 1/18. 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.
Tue 4/73:58 pm
EYW
-
PDX
1 stop10h 54m
American Airlines
Sun 4/1212:59 am
PDX
-
EYW
2 stops12h 31m
American Airlines
Deal found 1/18$359
This American Airlines deal was found by Cheapflights users on 1/18. 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 3/612:55 pm
EYW
-
PDX
1 stop10h 49m
American Airlines
Sun 3/89:44 pm
PDX
-
EYW
1 stop10h 27m
American Airlines
Deal found 1/18$463
This United Airlines deal was found by Cheapflights users on 1/19. 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.
Sat 1/242:05 pm
EYW
-
PDX
1 stop10h 44m
United Airlines
Wed 1/2811:05 pm
PDX
-
EYW
1 stop10h 58m
United Airlines
Deal found 1/19$497
This Delta deal was found by Cheapflights users on 1/19. 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.
Sat 1/247:10 am
EYW
-
PDX
2 stops12h 17m
Delta
Wed 1/285:25 pm
PDX
-
EYW
2 stops15h 00m
Delta
Deal found 1/19$508
This United Airlines deal was found by Cheapflights users on 1/19. 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 1/234:15 pm
EYW
-
PDX
1 stop9h 17m
United Airlines
Tue 1/2711:05 pm
PDX
-
EYW
1 stop10h 58m
United Airlines
Deal found 1/19$529
This American Airlines deal was found by Cheapflights users on 1/19. 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 1/231:22 pm
EYW
-
PDX
1 stop10h 02m
American Airlines
Tue 1/275:25 am
PDX
-
EYW
2 stops13h 22m
American Airlines
Deal found 1/19$534
This American Airlines deal was found by Cheapflights users on 1/19. 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 1/231:33 pm
EYW
-
PDX
2 stops11h 38m
American Airlines
Wed 1/286:00 am
PDX
-
EYW
2 stops12h 47m
American Airlines
Deal found 1/19$540

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 January 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$329
(American Airlines)
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
Search Deals

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 January 20, 2026.
Use the filters below to find and compare flights from Key West to Portland that are best for you.

Fly from

Key West

Fly to

Portland

Route

Depart

Return

Price

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 4/7

3:58 pm-11:52 pm

1 stop10h 54m

Portland

Mon 4/13

11:59 pm-12:37 pm

1 stop9h 38m

$329

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 5/14

3:58 pm-11:52 pm

1 stop10h 54m

Portland

Sat 5/23

10:30 pm-1:42 pm

1 stop12h 12m

$329

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 3/6

12:55 pm-8:44 pm

1 stop10h 49m

Portland

Sun 3/8

9:44 pm-11:11 am

1 stop10h 27m

$463

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 5/10

3:58 pm-11:52 pm

1 stop10h 54m

$380

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 5/10

12:04 pm-4:49 pm

2 stops31h 45m

$414

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 5/10

11:04 am-10:53 pm

3 stops38h 49m

$434

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

  • 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 January 20, 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
7.2
Good
11,163 reviews

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,163 reviews
American Airlines
7.2
Good
11,163 reviews

Comfort

7.2

Boarding

7.5

Food

6.4

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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 54m. 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
Vancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Beaverton
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Tillamook
Pacific City
Gresham

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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 January 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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