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$252+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Jan 9 — Jan 161
Thu 1/9
Thu 1/16
1 adult, Economy
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The best prices from Portland to Key West are usually found in August or September, booked 40 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 January 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$309
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$415
Provider with most accurate pricing for Portland-Key West flight deals.
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Provider most trusted by Cheapflights users for Portland-Key West flights.
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From Portland to Key West
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High demand for flights, 15% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 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 January 4, 2025.

This American Airlines deal was found by Cheapflights users on 1/3. 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 3/45:31 amPDX - EYW
1 stop7h 49mAmerican Airlines
Tue 3/113:57 pmEYW - PDX
1 stop10h 14mAmerican Airlines
Deal found 1/3$309
This United Airlines deal was found by Cheapflights users on 1/3. 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.
Sun 2/210:48 pmPDX - EYW
1 stop10h 59mUnited Airlines
Sun 2/93:50 pmEYW - PDX
1 stop10h 07mUnited Airlines
Deal found 1/3$384
This Delta deal was found by Cheapflights users on 1/3. 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.
Mon 3/312:59 amPDX - EYW
2 stops10h 09mDelta
Tue 3/117:00 amEYW - PDX
2 stops14h 45mDelta
Deal found 1/3$414
This Orbitz deal was found by Cheapflights users on 1/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/36:26 pmPDX - EYW
2 stops15h 49mMultiple Airlines
Fri 2/710:55 amEYW - PDX
2 stops15h 48mMultiple Airlines
Deal found 1/3$446
This Alaska Airlines deal was found by Cheapflights users on 1/4. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/15:20 pmPDX - EYW
2 stops15h 26mAlaska Airlines
Sun 4/612:11 pmEYW - PDX
2 stops13h 44mAlaska Airlines
Deal found 1/4$979

Find flights from Portland to Key West within your budget

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 January 4, 2025.

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Depart

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Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 3/4

5:31 am-4:20 pm

1 stop7h 49m

Key West

Tue 3/11

3:57 pm-11:11 pm

1 stop10h 14m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 2/2

10:48 pm-12:47 pm

1 stop10h 59m

Key West

Sun 2/9

3:50 pm-10:57 pm

1 stop10h 07m

$384

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 3/3

12:59 am-2:08 pm

2 stops10h 09m

Key West

Tue 3/11

7:00 am-6:45 pm

2 stops14h 45m

$414

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 2/3

6:26 pm-1:15 pm

2 stops15h 49m

Key West

Fri 2/7

10:55 am-11:43 pm

2 stops15h 48m

$446

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 5/25

11:59 pm-6:55 pm

2 stops15h 56m

$252

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 5/25

6:04 am-7:44 pm

1 stop10h 40m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

Compare providers for flights from Portland to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Key West in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland-Key West 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 Portland-Key West 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 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.

Travel insights for flights from Portland to Key West

Get recent, data-driven insights about flights from Portland to Key West including ideal travel times, pricing trends, and more.

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 December 27, 2024.

To ensure you get the cheapest price possible for a flight from Portland to Key West, you should look to book at least 40 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 $536). 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.

Rainfall in Key West by month

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

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

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

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 January 4, 2025.
Alaska Airlines
8.0
Very good
9,606 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 10

One or two midday non-stop flights from PDX to Santa Rosa would be great. The very early and late options are hard on older passengers.

Alaska Airlines
8.0
Very good
9,606 reviews
Alaska Airlines
8.0
Very good
9,606 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 10

One or two midday non-stop flights from PDX to Santa Rosa would be great. The very early and late options are hard on older passengers.

Delta
8.0
Very good
8,526 reviews
Alaska Airlines
8.0
Very good
9,606 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 10

One or two midday non-stop flights from PDX to Santa Rosa would be great. The very early and late options are hard on older passengers.

United Airlines
7.4
Good
8,963 reviews
Alaska Airlines
8.0
Very good
9,606 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 10

One or two midday non-stop flights from PDX to Santa Rosa would be great. The very early and late options are hard on older passengers.

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,606 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

7.1

Crew

8.5

Food

7.1

Reviews

1 / 10

One or two midday non-stop flights from PDX to Santa Rosa would be great. The very early and late options are hard on older passengers.

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 $309, was found to be the cheapest airline from Portland to Key West.Alternate airlines to your destination round-trip include United Airlines and Delta. American Airlines is priced at 41% 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 $536). 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 2 airlines flying from Portland to Key West

Discover the top 2 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 January 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$288Average$572FlexibilityNo cancel feeOn-time71%
DeltaCheapest$307Average$413FlexibilityNo cancel feeOn-timeN/A
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