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$265+ 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 6/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
abr. 20 — abr. 271
dom. 4/20
dom. 4/27
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 abril 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$344
(American Airlines)

One-way from

$265
(Delta)

Popular in

August

Cheapest in

September

Average price

$574
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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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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 abril 15, 2025.

This American Airlines deal was found by Cheapflights users on 4/15. 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.
mié. 5/71:39 pmEYW - PDX
2 stops13h 20mAmerican Airlines
lun. 5/1211:49 pmPDX - EYW
2 stops10h 50mAmerican Airlines
Deal found 4/15$344
This United deal was found by Cheapflights users on 4/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/72:18 pmEYW - PDX
1 stop10h 21mUnited Airlines
lun. 5/1210:47 pmPDX - EYW
1 stop11h 16mUnited Airlines
Deal found 4/15$434
This Delta deal was found by Cheapflights users on 4/15. 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.
mar. 4/2212:25 pmEYW - PDX
2 stops12h 57mDelta
lun. 4/2812:59 amPDX - EYW
2 stops10h 06mDelta
Deal found 4/15$560
This Mytrip deal was found by Cheapflights users on 4/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/185:10 pmEYW - PDX
3 stops27h 55mMultiple Airlines
mié. 4/307:01 pmPDX - EYW
2 stops18h 48mMultiple Airlines
Deal found 4/15$711

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 abril 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

mié. 5/7

1:39 pm-11:59 pm

2 stops13h 20m

Portland

lun. 5/12

11:49 pm-1:39 pm

2 stops10h 50m

$344

Key WestPortland

EYW - PDX

EYWPDX

Key West

mié. 5/7

2:18 pm-9:39 pm

1 stop10h 21m

Portland

lun. 5/12

10:47 pm-1:03 pm

1 stop11h 16m

$434

Key WestPortland

EYW - PDX

EYWPDX

Key West

vie. 4/25

12:25 pm-6:45 pm

1 stop9h 20m

Portland

vie. 4/25

12:59 am-5:17 pm

2 stops13h 18m

$849

Key WestPortland

EYW - PDX

EYWPDX

Key West

mié. 6/25

2:05 pm-10:45 pm

2 stops11h 40m

$265

Key WestPortland

EYW - PDX

EYWPDX

Key West

lun. 6/30

6:45 pm-7:19 pm

2 stops27h 34m

$269

Key WestPortland

EYW - PDX

EYWPDX

Key West

vie. 6/27

1:00 pm-8:48 pm

1 stop10h 48m

$349

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

  • 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 abril 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Portland when rainfall is around 0.7 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

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 abril 15, 2025.
See what other customers who have flown with Delta, United Airlines and American Airlines from Key West to Portland have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Delta
8.0
Very good
7,917 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
United Airlines
7.4
Good
8,658 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,917 reviews

Entertainment

7.9

Overall

8.0

Comfort

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
2.0
Mediocre

Santiago,Apr 2024

MCO - ATL

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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.

  • What are the cheapest airlines flying from Key West to Portland round-trip?

    Cheapflights users have booked flights from Key West to Portland round-trip from $344. Other airlines that can offer you cheap pricing are United Airlines, from $434, and Delta, from $849. American Airlines is 33% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Key West to Portland one-way?

    One-way options have recently been found by users for as low as $265 on Delta. Other airlines that offer cheap prices include United Airlines from $269 and American Airlines from $349 one-way.

  • 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 $369). 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 Key West?

Book flights to Key West if you plan to visit one of these locations
Beaverton
Lincoln City
Seaside
Clackamas
Vancouver
McMinnville
Lake Oswego
Hillsboro
Gresham
Astoria
Long Beach
Cannon Beach
Tigard
Hood River
Woodburn
Depoe Bay
Pacific City
Stevenson
Troutdale
Longview

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Top 2 airlines flying from Key West to Portland

Discover the top 2 airlines 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 abril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$543FlexibilityNo cancel feeOn-time71%

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