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

American Airlines, at $294, was found to be the cheapest airline from Portland, Maine to Key West.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is currently priced 27% below the average price you’ll pay for this route.

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

$179 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $184 and $246, respectively.

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

Travelers seeking maximum savings on their Portland, Maine to Key West flight should consider departing on Tuesday mornings when fares are most often at their lowest. Thursday 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, Maine to Key West?

Before booking your flight from Portland, Maine to Key West check out the most popular airlines for this route: American Airlines, Delta or United Airlines.

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

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 27% on the overall cost on flights from Portland, Maine to Key West.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 48 days in advance, which can save you up to 73% on flights from Portland, Maine to Key West compared to booking the week you need them. Waiting 48 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $335. For sooner than that we have options available in the next 3 days from $390.

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

Flights from Portland, Maine to Key West lean towards being more expensive in March. Prices are generally better when you fly from Portland, Maine to Key West in June, with the cheapest ticket starting at $268.

Most accurate provider : When it comes to deals on Portland, Maine-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, Maine-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Key West flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Portland, Maine-Key West flights, Cheapflights users trust eDreams the most. eDreams 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, Maine-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.

$179+ Flights from Portland, ME 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.

3. Compare prices and book

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Cheapflights Tip: The best prices from Portland to Key West are usually found in June or August, booked 47 days in advance, depart on a Tuesday or Wednesday and return on a Monday

Cheap flight deals from Portland to Key West

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$294 (American Airlines)
One-way from	$179 (Delta)
Popular in	March
Cheapest in	June
Average price	$428

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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One-way flight from Portland to Key West

Search Deals

Highest demand for flights based on searches. 18% potential increase in price ($95 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 4% potential price decrease ($16 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 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 22, 2025.

Sat 5/107:35 amPWM - EYW

1 stop6h 14mAmerican Airlines

Thu 5/153:17 pmEYW - PWM

1 stop7h 49mAmerican Airlines

Deal found 4/21

$294

Tue 6/35:30 amPWM - EYW

1 stop7h 26mDelta

Mon 6/96:29 pmEYW - PWM

1 stop5h 57mDelta

Deal found 4/21

$364

Tue 5/66:00 amPWM - EYW

1 stop7h 03mUnited Airlines

Sat 5/108:45 amEYW - PWM

2 stops15h 14mUnited Airlines

Deal found 4/21

$453

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 22, 2025.

Sat 5/107:35 amPWM - EYW

1 stop6h 14mAmerican Airlines

Thu 5/153:17 pmEYW - PWM

1 stop7h 49mAmerican Airlines

Deal found 4/21

$294

Tue 6/35:30 amPWM - EYW

1 stop7h 26mDelta

Mon 6/96:29 pmEYW - PWM

1 stop5h 57mDelta

Deal found 4/21

$364

Tue 5/66:00 amPWM - EYW

1 stop7h 03mUnited Airlines

Sat 5/108:45 amEYW - PWM

2 stops15h 14mUnited Airlines

Deal found 4/21

$453

Last-minute flights from Portland to Key West
Discover last-minute flight deals from Portland to Key West. Data last updated April 22, 2025 and is based on user searches.

Sat 5/105:50 amPWM - EYW

1 stop5h 42mAmerican Airlines

Thu 5/155:24 pmEYW - PWM

1 stop5h 42mAmerican Airlines

Deal found 4/22

$294

Thu 5/155:30 amPWM - EYW

2 stops12h 35mUnited Airlines

Sun 5/188:45 amEYW - PWM

2 stops15h 14mUnited Airlines

Deal found 4/22

$771

Thu 5/1511:33 amPWM - EYW

2 stops8h 34mDelta

Sun 5/186:25 pmEYW - PWM

1 stop5h 34mDelta

Deal found 4/22

$1,008

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 22, 2025.

Thu 7/312:55 pmPWM - EYW

1 stop6h 44mDelta

Deal found 4/21

$179

Thu 7/37:41 amPWM - EYW

2 stops11h 21mAmerican Airlines

Deal found 4/21

$184

Fri 4/256:15 amPWM - EYW

1 stop6h 44mUnited Airlines

Deal found 4/22

$246

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

PWM - EYW

PWMEYW

Portland

Sat 5/10

7:35 am-1:49 pm

1 stop6h 14m

Key West

Thu 5/15

3:17 pm-11:06 pm

1 stop7h 49m

$294

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 6/3

5:30 am-12:56 pm

1 stop7h 26m

Key West

Mon 6/9

6:29 pm-12:26 am

1 stop5h 57m

$364

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 5/6

6:00 am-1:03 pm

1 stop7h 03m

Key West

Sat 5/10

8:45 am-11:59 pm

2 stops15h 14m

$453

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

12:55 pm-7:39 pm

1 stop6h 44m

$179

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

7:41 am-7:02 pm

2 stops11h 21m

$184

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

5:35 am-2:00 pm

3 stops32h 25m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

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*2 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, Maine-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, Maine-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Key West flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Portland, Maine-Key West flights, Cheapflights users trust eDreams the most. eDreams 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, Maine-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, Maine to Key West?

To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 47 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, Maine to Key West?

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

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

It’s typically best to fly out from Portland, Maine to Key West in the morning. Doing so could potentially save you 13% on the flight price compared to flying at noon, which is usually more expensive.

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

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

7,920 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,683 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,920 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

What are the cheapest airlines flying from Portland, Maine to Key West round-trip?
American Airlines, at $294, was found to be the cheapest airline from Portland, Maine to Key West.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is currently priced 27% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Portland, Maine to Key West one-way?
$179 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $184 and $246, 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, Maine to Key West?
Currently, August is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $328). Flying from Portland, Maine 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
Delta	Cheapest$246	Average$385	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$268	Average$423	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$346	Average$588	FlexibilityNo cancel fee	On-time69%

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$179+ Cheap flights from Portland, ME to Key West (PWM - 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 7/3. 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 June or August, booked 47 days in advance, depart on a Tuesday or Wednesday and return on a Monday

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 22, 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 22, 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, Maine 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 18, 2025.

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

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

Find hourly flight availability from Portland to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.

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

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, Maine to Key West round-trip?

What are the cheapest airlines to fly from Portland, Maine 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, Maine 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 22, 2025.