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$212+ Cheap flights from Portland to Key West (PDX - EYW)

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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in August or September, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Portland to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Key West (EYW). 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 July 1, 2025.

Round-trip from

$389
(American Airlines)

One-way from

$212
(Delta)

Popular in

June

Cheapest in

August

Average price

$568
From Portland to Key West
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One-way flight from Portland to Key West
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Highest demand for flights based on searches. 14% potential increase in price ($94 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find flight deals from Portland to Key West

Cheapest flights from Portland to Key West
Explore the most affordable flight options available from Portland to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 1, 2025.

This American Airlines deal was found by Cheapflights users on 6/30. 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 9/249:56 pmPDX - EYW
1 stop11h 09mAmerican Airlines
Sat 9/2712:00 pmEYW - PDX
1 stop11h 37mAmerican Airlines
Deal found 6/30$389
This Delta deal was found by Cheapflights users on 7/1. 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 9/1210:05 pmPDX - EYW
1 stop9h 50mDelta
Fri 9/192:00 pmEYW - PDX
2 stops11h 39mDelta
Deal found 7/1$396
This Mytrip deal was found by Cheapflights users on 6/30. 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.
Wed 7/303:10 pmPDX - EYW
3 stops21h 20mMultiple Airlines
Wed 8/610:02 amEYW - PDX
3 stops26h 16mMultiple Airlines
Deal found 6/30$509
This United Airlines deal was found by Cheapflights users on 6/29. 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 7/265:25 amPDX - EYW
2 stops28h 16mUnited Airlines
Tue 7/292:12 pmEYW - PDX
3 stops28h 02mUnited Airlines
Deal found 6/29$698

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Key West 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 July 1, 2025.
Use the filters below to find and compare flights from Portland to Key West that are best for you.

Fly from

Portland

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 9/24

9:56 pm-12:05 pm

1 stop11h 09m

Key West

Sat 9/27

12:00 pm-8:37 pm

1 stop11h 37m

$389

PortlandKey West

PDX - EYW

PDXEYW

Portland

Fri 9/12

10:05 pm-10:55 am

1 stop9h 50m

Key West

Fri 9/19

2:00 pm-10:39 pm

2 stops11h 39m

$396

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 7/30

3:10 pm-3:30 pm

3 stops21h 20m

Key West

Wed 8/6

10:02 am-9:18 am

3 stops26h 16m

$509

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 7/26

5:25 am-12:41 pm

2 stops28h 16m

Key West

Tue 7/29

2:12 pm-3:14 pm

3 stops28h 02m

$698

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/29

9:30 pm-10:51 am

1 stop10h 21m

$212

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 7/28

12:59 am-4:18 pm

2 stops12h 19m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Best time to book a flight from Portland to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Portland 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 Portland to Key West

How far ahead should I book a flight from Portland to Key West?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Key West. Price data was last updated on June 27, 2025.

To ensure you get the cheapest price possible for a flight from Portland to Key West, you should look to book at least 67 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland to Key West in March is currently the most expensive (average of $493). 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.

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated July 1, 2025.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Portland to Key West to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,852 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Portland to Key West. 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 Portland to Key West round-trip?

    American Airlines, at $389, was found to be the cheapest airline from Portland to Key West.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is priced at 28% lower than the current average price of a flight leaving 3 months from now.

  • Can I find deals for flights from Portland to Key West that include hotel bookings?

    Yes. In addition to deals on Portland to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Key West.

  • Can I find deals for business class flights from Portland to Key West?

    Yes. Cheapflights offers flight deals from Portland to Key West 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 Portland to Key West?

    Currently, August is the cheapest month in which you can book a flight from Portland to Key West (average of $328). Flying from Portland to Key West in March is currently the most expensive (average of $493). 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.

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Top 3 airlines flying from Portland to Key West

Discover the top 3 airlines that operate flights from Portland to Key West. 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$274Average$570FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$622FlexibilityNo cancel feeOn-time69%

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