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

American Airlines, at $261, 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 51% lower than the current average price of a flight leaving 3 months from now.

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

$131 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $201 and $485, respectively.

What is the cheapest day to fly from Portland to Key West?

Travelers seeking maximum savings on their Portland to Key West flight should consider departing on Tuesday evenings when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Portland to Key West?

When booking a flight from Portland to Key West, you may want to consider flying on American Airlines, Delta or United Airlines as they are the most popular for this route.

What is the cheapest day to fly round-trip from Portland to Key West?

Departing on a Sunday is a good option for securing a great price. You can expect to save up to 31% when planning your travel around this day of the week.

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

Users have found that booking a flight from Portland to Key West at least 22 days early can save you up to 93% on average compared to booking a flight this week. If booking 22 days before your flight isn’t an option for you, users have found flights from Portland to Key West for as little as $404 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $868 for flights departing within the next 3 days.

What is the cheapest month to fly from Portland to Key West?

Our data shows that September tends to be the cheapest month to fly to Key West from Portland. Users have commonly found prices around $537 for the month, but tickets can be as low as $277. Due to multiple factors, prepare for potentially higher prices in March.

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

Unlike in the morning, when flights are generally more expensive, you can save up to 8% on flights from Portland to Key West by exploring options for tickets in the afternoon.

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.

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.

$131+ Flights from Portland to Key West

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1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Key West are usually found in September or August, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Portland to Key West

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$261 (American Airlines)
One-way from	$131 (American Airlines)
Popular in	March
Cheapest in	September
Average price	$593

Provider with most accurate pricing for Portland-Key West flight deals.

Search Deals

Provider most trusted by Cheapflights users for Portland-Key West flights.

Search Deals

From Portland to Key West

Search Deals

One-way flight from Portland to Key West

Search Deals

Highest demand for flights based on searches. 13% potential increase in price ($82 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

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 April 10, 2025.

Sat 5/311:52 pmPDX - EYW

2 stops11h 06mAmerican Airlines

Wed 5/73:17 pmEYW - PDX

2 stops11h 42mAmerican Airlines

Deal found 4/9

$261

Mon 5/510:47 pmPDX - EYW

1 stop11h 16mUnited Airlines

Fri 5/96:45 pmEYW - PDX

2 stops31h 19mUnited Airlines

Deal found 4/9

$463

Tue 4/156:00 amPDX - EYW

1 stop8h 17mDelta

Tue 4/2212:25 pmEYW - PDX

2 stops14h 19mDelta

Deal found 4/9

$475

Thu 4/242:32 pmPDX - EYW

2 stops22h 44mMultiple Airlines

Mon 4/289:51 amEYW - PDX

2 stops35h 14mMultiple Airlines

Deal found 4/9

$487

Best flights from Portland to Key West
Discover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 10, 2025.

Sat 5/311:52 pmPDX - EYW

2 stops11h 06mAmerican Airlines

Wed 5/73:17 pmEYW - PDX

2 stops11h 42mAmerican Airlines

Deal found 4/9

$261

Mon 5/510:47 pmPDX - EYW

1 stop11h 16mUnited Airlines

Fri 5/96:45 pmEYW - PDX

2 stops31h 19mUnited Airlines

Deal found 4/9

$463

Thu 4/242:32 pmPDX - EYW

2 stops22h 44mMultiple Airlines

Mon 4/289:51 amEYW - PDX

2 stops35h 14mMultiple Airlines

Deal found 4/9

$487

Tue 4/297:23 amPDX - EYW

2 stops10h 07mDelta

Sat 5/37:00 amEYW - PDX

2 stops11h 53mDelta

Deal found 4/9

$544

Last-minute flights from Portland to Key West
Discover last-minute flight deals from Portland to Key West. Data last updated April 10, 2025 and is based on user searches.

Tue 4/155:31 amPDX - EYW

1 stop7h 45mAmerican Airlines

Tue 4/2212:59 pmEYW - PDX

1 stop10h 36mAmerican Airlines

Deal found 4/9

$470

Tue 4/156:00 amPDX - EYW

1 stop8h 17mDelta

Tue 4/2212:25 pmEYW - PDX

2 stops14h 19mDelta

Deal found 4/9

$475

Tue 4/157:30 pmPDX - EYW

2 stops33h 30mUnited Airlines

Tue 4/222:45 pmEYW - PDX

3 stops31h 00mUnited Airlines

Deal found 4/9

$771

Thu 4/242:32 pmPDX - EYW

2 stops22h 44mMultiple Airlines

Mon 4/289:51 amEYW - PDX

2 stops35h 14mMultiple Airlines

Deal found 4/9

$487

Sat 5/311:52 pmPDX - EYW

2 stops11h 06mAmerican Airlines

Wed 5/73:17 pmEYW - PDX

2 stops11h 42mAmerican Airlines

Deal found 4/9

$261

Mon 5/510:47 pmPDX - EYW

1 stop11h 16mUnited Airlines

Fri 5/96:45 pmEYW - PDX

2 stops31h 19mUnited Airlines

Deal found 4/9

$463

One-way flights from Portland to Key West
Search for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated April 10, 2025.

Tue 7/2911:54 pmPDX - EYW

2 stops10h 57mAmerican Airlines

Deal found 4/9

$131

Wed 4/2311:00 pmPDX - EYW

1 stop10h 59mUnited Airlines

Deal found 4/9

$201

Wed 4/237:01 pmPDX - EYW

2 stops18h 48mMultiple Airlines

Deal found 4/9

$202

Tue 4/2212:59 amPDX - EYW

2 stops13h 18mDelta

Deal found 4/9

$485

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Key West that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 5/3

11:52 pm-1:58 pm

2 stops11h 06m

Key West

Wed 5/7

3:17 pm-11:59 pm

2 stops11h 42m

$261

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 5/5

10:47 pm-1:03 pm

1 stop11h 16m

Key West

Fri 5/9

6:45 pm-11:04 pm

2 stops31h 19m

$463

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 4/24

2:32 pm-4:16 pm

2 stops22h 44m

Key West

Mon 4/28

9:51 am-6:05 pm

2 stops35h 14m

$487

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 4/29

7:23 am-8:30 pm

2 stops10h 07m

Key West

Sat 5/3

7:00 am-3:53 pm

2 stops11h 53m

$544

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/29

11:54 pm-1:51 pm

2 stops10h 57m

$131

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 4/23

11:00 pm-12:59 pm

1 stop10h 59m

$201

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 4/23

7:01 pm-4:49 pm

2 stops18h 48m

$202

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 4/22

12:59 am-5:17 pm

2 stops13h 18m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/9

Compare providers for flights from Portland to Key West

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 April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*3 stars
eDreams	Price Accuracy3 stars	Trust 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.

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?

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.

Rainfall in Key West 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

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

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

7,907 reviews

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

7,907 reviews

Delta

8.0

Very good

7,907 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

United Airlines

7.4

Good

8,634 reviews

Delta

8.0

Very good

7,907 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,907 reviews

Reviews

1 / 20

2.0

Mediocre

Joseph,Aug 2023

MSP - MCO

Related info for your journey

What are the cheapest airlines flying from Portland to Key West round-trip?
American Airlines, at $261, 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 51% lower than the current average price of a flight leaving 3 months from now.
What are the cheapest airlines to fly from Portland to Key West one-way?
$131 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on United Airlines and Delta, with prices starting from $201 and $485, respectively.
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.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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Other flights to Key West

Top 3 airlines flying from Portland to Key West

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$284	Average$563	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$289	Average$410	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$317	Average$570	FlexibilityNo cancel fee	On-time69%

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$131+ 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.

Find cheap flights from Portland to Key West with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Portland to Key West are usually found in September or August, booked 69 days in advance, depart on a Monday or Tuesday and return on a Wednesday

Cheap flight deals from Portland to Key West

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Portland to Key West

Cheapest flights from Portland to Key WestExplore 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 April 10, 2025.

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 April 10, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Portland to Key West that are best for you.

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 April.

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.

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 April 4, 2025.

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

Rainfall in Key West by month

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

Temperature in Key West by month

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

Reviews of airlines servicing Key West

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.

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?

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

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

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

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

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from Portland to Key West

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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 April 10, 2025.