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$194+ 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
déc. 6 — déc. 131
sam. 12/6
sam. 12/13
1 adult, Economy
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Find 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 novembre 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/4. 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.
jeu. 11/202:39 pmEYW - PDX
1 stop9h 41mAmerican Airlines
lun. 11/245:30 amPDX - EYW
1 stop7h 59mAmerican Airlines
Deal found 11/4$389

Cheap 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 novembre 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
1 star

Round-trip from

$389
(American Airlines)

One-way from

$194
(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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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 novembre 6, 2025.
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

jeu. 11/20

2:39 pm-9:20 pm

1 stop9h 41m

Portland

lun. 11/24

5:30 am-4:29 pm

1 stop7h 59m

$389

Key WestPortland

EYW - PDX

EYWPDX

Key West

ven. 3/6

2:22 pm-9:54 pm

1 stop10h 32m

Portland

mar. 3/10

10:56 pm-1:09 pm

1 stop11h 13m

$492

Key WestPortland

EYW - PDX

EYWPDX

Key West

ven. 3/6

6:07 pm-7:03 pm

1 stop27h 56m

Portland

mar. 3/10

7:55 pm-11:03 am

2 stops12h 08m

$523

Key WestPortland

EYW - PDX

EYWPDX

Key West

ven. 3/6

4:02 pm-11:59 pm

1 stop10h 57m

Portland

mar. 3/10

8:01 am-11:59 pm

2 stops12h 58m

$533

Key WestPortland

EYW - PDX

EYWPDX

Key West

lun. 12/22

1:10 pm-11:43 am

2 stops25h 33m

$194

Key WestPortland

EYW - PDX

EYWPDX

Key West

lun. 12/22

4:03 pm-12:59 am

1 stop11h 56m

$304

Key WestPortland

EYW - PDX

EYWPDX

Key West

mer. 12/31

3:09 pm-10:39 pm

1 stop10h 30m

$393

Key WestPortland

EYW - PDX

EYWPDX

Key West

jeu. 12/18

4:03 pm-12:54 am

2 stops11h 51m

$823

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

  • 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.

Cheapflights Insights

Everything you need to know about your flight from Key West to Portland

What is the cheapest time of day to fly from EYW to PDX?

Find hourly flight availability from Key West to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated novembre 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Key West to Portland in the evening. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.

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 novembre 6, 2025.
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
11,040 reviews

Food

6.4

Crew

8.0

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Food

6.4

Crew

8.0

Comfort

7.2

Entertainment

6.9

Overall

7.2

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 9h 41m. Airlines will cover a distance of 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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
Lake Oswego
Beaverton
McMinnville
Hillsboro
Cannon Beach
Long Beach
Longview
Tigard
The Dalles
Depoe Bay
Stevenson
Wilsonville
Pacific City
Tillamook
Gresham
Troutdale

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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 novembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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