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Key West

$164+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Nov 12 — Nov 191
Wed 11/12
Wed 11/19
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in June or August, booked 90 days in advance, depart on a Tuesday or Wednesday and return on a Monday

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 October 13, 2025.

This American Airlines deal was found by Cheapflights users on 10/10. 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.
Sat 12/137:11 amPWM - EYW
1 stop9h 01mAmerican Airlines
Mon 12/157:00 amEYW - PWM
2 stops9h 28mAmerican Airlines
Deal found 10/10$274
This Delta deal was found by Cheapflights users on 10/11. 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.
Thu 10/301:27 pmPWM - EYW
1 stop6h 39mDelta
Thu 11/61:57 pmEYW - PWM
1 stop8h 22mDelta
Deal found 10/11$294
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:05 pmPWM - EYW
2 stops16h 02mBreeze Airways
Wed 11/510:47 amEYW - PWM
1 stop6h 51mBreeze Airways
Deal found 10/12$295
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/23:15 pmPWM - EYW
1 stop26h 31mMultiple Airlines
Thu 11/68:55 amEYW - PWM
1 stop24h 11mMultiple Airlines
Deal found 10/11$304
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:15 pmPWM - EYW
1 stop28h 40mMultiple Airlines
Wed 11/510:47 amEYW - PWM
1 stop6h 51mMultiple Airlines
Deal found 10/11$305
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:05 pmPWM - EYW
2 stops16h 02mBreeze Airways
Sun 11/98:55 amEYW - PWM
1 stop24h 11mBreeze Airways
Deal found 10/12$307
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/63:15 pmPWM - EYW
1 stop18h 05mMultiple Airlines
Sat 11/810:47 amEYW - PWM
1 stop6h 51mMultiple Airlines
Deal found 10/11$312
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:15 pmPWM - EYW
1 stop28h 40mMultiple Airlines
Sat 11/810:47 amEYW - PWM
1 stop6h 51mMultiple Airlines
Deal found 10/12$314
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/23:15 pmPWM - EYW
1 stop26h 31mMultiple Airlines
Sun 11/98:55 amEYW - PWM
1 stop24h 11mMultiple Airlines
Deal found 10/12$316
This Kiwi.com deal was found by Cheapflights users on 10/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/303:15 pmPWM - EYW
1 stop28h 40mMultiple Airlines
Sun 11/98:55 amEYW - PWM
1 stop24h 11mMultiple Airlines
Deal found 10/11$318

Cheap flight deals from Portland to Key West

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) 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 October 13, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(United Airlines)

One-way from

$164
(Delta)

Popular in

March

Cheapest in

June

Average price

$396
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. 15% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 13, 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

PWM - EYW

PWMEYW

Portland

Thu 10/30

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Mon 11/3

1:57 pm-10:19 pm

1 stop8h 22m

$294

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 10/30

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Fri 11/7

1:57 pm-12:05 am

2 stops10h 08m

$299

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 10/30

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Wed 11/5

7:40 am-4:13 pm

2 stops8h 33m

$299

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 11/1

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Thu 11/6

1:57 pm-12:05 am

2 stops10h 08m

$299

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 10/30

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Thu 11/6

1:57 pm-12:05 am

2 stops10h 08m

$299

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 11/4

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Fri 11/7

1:57 pm-10:19 pm

1 stop8h 22m

$327

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 10/26

6:00 am-11:27 am

1 stop5h 27m

Key West

Thu 10/30

1:57 pm-10:19 pm

1 stop8h 22m

$327

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 11/4

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Wed 11/5

1:57 pm-10:19 pm

1 stop8h 22m

$327

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/31

5:30 am-1:12 pm

1 stop7h 42m

Key West

Wed 4/1

2:35 pm-9:59 pm

1 stop7h 24m

$327

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 11/3

1:27 pm-8:06 pm

1 stop6h 39m

Key West

Thu 11/6

1:57 pm-10:19 pm

1 stop8h 22m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/11

Showing 1-10 of 17 results
1
2

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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust 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, 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 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, 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?

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 October 10, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 38 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, September is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $179). Flying from Portland, Maine to Key West in April is currently the most expensive (average of $292). 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 October 13, 2025.
Read through reviews of airlines operating flights from Portland to Key West, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,971 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
8.0
Very good
7,971 reviews
Delta
8.0
Very good
7,971 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,970 reviews
Delta
8.0
Very good
7,971 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,046 reviews
Delta
8.0
Very good
7,971 reviews

Crew

8.5

Entertainment

7.9

Overall

8.0

Boarding

8.2

Food

7.3

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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.

  • How long is the flight from Portland, Maine to Key West?

    Delta can get you from Portland, Maine to Key West in just under 6h 39m. Your travel time can differ by up to . Airlines will cover a distance of 1468 mi.

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

    American Airlines, at $268, 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 35% below the average price you’ll pay for this route.

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $179). Flying from Portland, Maine to Key West in April is currently the most expensive (average of $292). 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

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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 October 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$436FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$373Average$578FlexibilityNo cancel feeOn-time69%

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