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Key West

$168+ 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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
May 21 — May 281
Thu 5/21
Thu 5/28
1 adult, Economy
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Cheap 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 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Sat 5/166:26 pm
PWM
-
EYW
1 stop15h 58m
Breeze Airways
Tue 5/191:14 pm
EYW
-
PWM
2 stops28h 31m
Breeze Airways
Deal found 4/19$305
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/243:11 pm
PWM
-
EYW
1 stop27h 21m
Multiple Airlines
Fri 5/2912:07 pm
EYW
-
PWM
1 stop21h 05m
Multiple Airlines
Deal found 4/18$313
This Delta deal was found by Cheapflights users on 4/18. 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.
Sat 5/92:05 pm
PWM
-
EYW
1 stop5h 44m
Delta
Wed 5/137:30 am
EYW
-
PWM
1 stop5h 40m
Delta
Deal found 4/18$317
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/910:50 am
PWM
-
EYW
2 stops11h 46m
American Airlines
Wed 5/1311:24 am
EYW
-
PWM
2 stops12h 02m
American Airlines
Deal found 4/17$327
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 6/147:56 pm
PWM
-
EYW
2 stops16h 35m
Multiple Airlines
Fri 6/193:25 pm
EYW
-
PWM
1 stop17h 47m
Multiple Airlines
Deal found 4/21$344
This American Airlines deal was found by Cheapflights users on 4/21. 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 10/206:06 am
PWM
-
EYW
1 stop6h 52m
American Airlines
Sat 10/241:26 pm
EYW
-
PWM
2 stops10h 11m
American Airlines
Deal found 4/21$346

Find 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 April 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$305
(Kiwi.com)

One-way from

$168
(Kiwi.com)

Popular in

February

Cheapest in

June

Average price

$456
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. 11% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 21, 2026.
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

Cheapest round-trip

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

6:00 am-11:29 am

1 stop5h 29m

Key West

Wed 5/13

5:03 pm-11:54 pm

1 stop6h 51m

$317
Quickest round-trip

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/9

2:05 pm-7:49 pm

1 stop5h 44m

Key West

Wed 5/13

7:30 am-1:10 pm

1 stop5h 40m

$317

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/16

6:26 pm-10:24 am

1 stop15h 58m

Key West

Wed 5/20

11:46 am-7:16 pm

2 stops31h 30m

$352

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 5/16

11:24 am-10:36 pm

2 stops11h 12m

Key West

Wed 5/20

11:24 am-11:26 pm

2 stops12h 02m

$389

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 5/11

6:00 am-3:07 pm

1 stop9h 07m

Key West

Fri 5/15

2:49 pm-11:23 pm

1 stop8h 34m

$447

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 5/5

6:00 am-12:40 pm

1 stop6h 40m

Key West

Sat 5/9

2:15 pm-8:48 pm

1 stop6h 33m

$483

PortlandKey West

PWM - EYW

PWMEYW

Portland

Fri 5/15

6:00 am-3:07 pm

1 stop9h 07m

Key West

Tue 5/19

2:49 pm-11:29 pm

1 stop8h 40m

$487
Cheapest one-way

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 4/27

5:06 pm-11:11 am

2 stops42h 05m

$185
Quickest one-way

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 4/28

6:00 am-12:40 pm

1 stop6h 40m

$224

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 4/28

4:28 pm-1:31 pm

3 stops21h 03m

$746

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 11 resultsSorted by cheapest first
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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 April 17, 2026.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 26 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, June is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $319). Flying from Portland, Maine to Key West in February is currently the most expensive (average of $572). 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.

How much does it cost to fly round-trip from Portland, Maine to Key West?

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 April 21, 2026.
Read through reviews of airlines operating flights from Portland to Key West, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,434 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,434 reviews
Delta
7.9
Good
8,434 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,613 reviews
Delta
7.9
Good
8,434 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,645 reviews
Delta
7.9
Good
8,434 reviews

Comfort

7.9

Overall

7.9

Boarding

8.1

Food

7.2

Crew

8.5

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    American Airlines and Delta can get you from Portland, Maine to Key West in just under 5h 29m. Your travel time can differ by up to 15m. Airlines will cover a distance of 1468 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Delta, at $256, was found to be the cheapest airline from Portland, Maine to Key West.Alternate airlines to your destination round-trip include United Airlines and American Airlines. Delta is currently priced 41% 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, June is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $319). Flying from Portland, Maine to Key West in February is currently the most expensive (average of $572). 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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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 April 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$256Average$437FlexibilityNo cancel feeOn-time69%
DeltaCheapest$256Average$437FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$445FlexibilityNo cancel feeOn-time71%

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