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$318+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$473
(American Airlines)

One-way from

$318
(American Airlines)
From Key West to Portland
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One-way flight from Key West to Portland
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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 September 15, 2025.

This American Airlines deal was found by Cheapflights users on 9/13. 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 10/102:32 pmEYW - PDX
1 stop10h 04mAmerican Airlines
Tue 10/145:34 amPDX - EYW
2 stops10h 48mAmerican Airlines
Deal found 9/13$473
This American Airlines deal was found by Cheapflights users on 9/13. 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 11/212:50 pmEYW - PDX
1 stop9h 25mAmerican Airlines
Fri 11/2810:45 pmPDX - EYW
1 stop9h 37mAmerican Airlines
Deal found 9/13$475
This Delta deal was found by Cheapflights users on 9/14. 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.
Fri 10/101:57 pmEYW - PDX
1 stop11h 11mDelta
Mon 10/1312:40 amPDX - EYW
2 stops9h 22mDelta
Deal found 9/14$758
This Delta deal was found by Cheapflights users on 9/13. 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.
Fri 11/217:40 amEYW - PDX
2 stops13h 03mDelta
Thu 11/2712:35 amPDX - EYW
2 stops13h 48mDelta
Deal found 9/13$936

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 September 15, 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

Fri 11/21

2:50 pm-9:15 pm

1 stop9h 25m

Portland

Fri 11/28

10:45 pm-11:22 am

1 stop9h 37m

$475

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 10/10

11:22 am-9:04 pm

2 stops12h 42m

Portland

Tue 10/14

11:59 pm-5:16 pm

2 stops14h 17m

$478

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 3/6

6:00 pm-7:18 pm

1 stop28h 18m

Portland

Tue 3/10

6:04 am-5:12 pm

1 stop8h 08m

$487

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 12/31

4:03 pm-12:59 am

1 stop11h 56m

$318

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 12/31

5:00 pm-7:43 pm

1 stop29h 43m

$382

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

4:18 pm-11:31 pm

1 stop10h 13m

$409

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

2:58 pm-10:21 pm

1 stop10h 23m

$439

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

4:00 pm-10:53 am

3 stops21h 53m

$787

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

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 September 15, 2025.

A simple way to save on the total cost of your ticket is to fly from Key West to Portland at noon. If you’re flexible enough to do this you can expect to save up to 29% 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 September 15, 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
10,000 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

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
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Crew

8.0

Entertainment

6.9

Overall

7.2

Boarding

7.5

Comfort

7.2

Food

6.4

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 25m. 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.

  • What is the cheapest month to book a flight from Key West to Portland?

    Currently, November is the cheapest month in which you can book a flight from Key West to Portland (average of $277). Flying from Key West to Portland in March is currently the most expensive (average of $368). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

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

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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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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