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$164+ Cheap flights from Key West to Portland, ME (EYW - PWM)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Nov 7 — Nov 141
Fri 11/7
Fri 11/14
1 adult, Economy
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Cheap flight deals from Key West to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Portland (PWM). 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 8, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$269
(Delta)

One-way from

$164
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$364
Provider with most accurate pricing for Key West-Portland flight deals.
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Provider most trusted by Cheapflights users for Key West-Portland flights.
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From Key West to Portland
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One-way flight from Key West to Portland
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Key West to Portland

Cheapest flights from Key West to Portland
Explore the most affordable flight options available from Key West to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 8, 2025.

This Delta deal was found by Cheapflights users on 10/8. 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 10/301:57 pmEYW - PWM
1 stop8h 22mDelta
Tue 11/41:27 pmPWM - EYW
1 stop6h 39mDelta
Deal found 10/8$269
This American Airlines deal was found by Cheapflights users on 10/8. 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.
Thu 10/303:20 pmEYW - PWM
1 stop6h 50mAmerican Airlines
Tue 11/47:02 amPWM - EYW
2 stops9h 59mAmerican Airlines
Deal found 10/8$274
This American Airlines deal was found by Cheapflights users on 10/8. 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 10/144:58 pmEYW - PWM
1 stop5h 50mAmerican Airlines
Mon 10/276:00 amPWM - EYW
1 stop6h 58mAmerican Airlines
Deal found 10/8$334
This American Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/174:53 pmEYW - PWM
1 stop5h 55mAmerican Airlines
Sun 10/197:44 amPWM - EYW
1 stop6h 08mAmerican Airlines
Deal found 10/6$405
This Delta deal was found by Cheapflights users on 10/7. 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.
Tue 10/141:57 pmEYW - PWM
1 stop8h 22mDelta
Tue 10/285:42 amPWM - EYW
2 stops11h 39mDelta
Deal found 10/7$493

Cheapflights Fare Finder

 
Customize your flight search to find flights from Key West to Portland 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 8, 2025.
Use the filters below to find and compare flights from Key West to Portland that are best for you.

Fly from

Key West

Fly to

Portland

Route

Depart

Return

Price

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 10/30

1:57 pm-10:19 pm

1 stop8h 22m

Portland

Tue 11/4

1:27 pm-8:06 pm

1 stop6h 39m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 10/30

1:25 pm-11:51 pm

2 stops10h 26m

Portland

Tue 11/4

7:02 am-5:01 pm

2 stops9h 59m

$279

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 3/27

12:30 pm-10:44 am

1 stop22h 14m

Portland

Tue 3/31

6:00 am-3:06 pm

1 stop9h 06m

$453

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 3/27

3:08 pm-10:30 pm

1 stop7h 22m

Portland

Tue 3/31

5:44 am-4:44 pm

2 stops11h 00m

$501

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

2:35 pm-9:59 pm

1 stop7h 24m

Portland

Mon 4/6

5:30 am-1:12 pm

1 stop7h 42m

$513

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 12/24

8:00 am-1:22 pm

1 stop5h 22m

$164

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sun 1/18

9:46 am-9:07 am

1 stop23h 21m

$165

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sat 2/14

6:31 am-4:35 pm

2 stops10h 04m

$169

Key WestPortland

EYW - PWM

EYWPWM

Key West

Sun 1/18

10:27 pm-4:26 pm

3 stops17h 59m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/6

Compare providers for flights from Key West to Portland

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

Have a flexible travel schedule? Discover the best time to fly to Portland from Key West 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 Key West to Portland

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

Currently, November is the cheapest month in which you can book a flight from Key West to Portland, Maine (average of $170). Flying from Key West to Portland, Maine in February is currently the most expensive (average of $331). 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 Key West to Portland, Maine?

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated October 8, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from Key West to Portland 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
7,969 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,969 reviews
Delta
8.0
Very good
7,969 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
11,042 reviews
Delta
8.0
Very good
7,969 reviews

Crew

8.5

Entertainment

7.9

Food

7.3

Comfort

7.9

Boarding

8.2

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from Key West to Portland. 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 Key West to Portland, Maine?

    Departing from Key West to Portland, Maine will take you 8h 22m. The distance between Key West and Portland, Maine is about 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 Key West to Portland, Maine round-trip?

    According to our current data, American Airlines ($268), and Delta ($274) offers the cheapest pricing from Key West to Portland, Maine. These flights start at 27% lower than the current average price 3 months from now.

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

    Yes. In addition to deals on Key West to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Portland.

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

    Yes. Cheapflights offers flight deals from Key West to Portland 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 Key West to Portland, Maine?

    Currently, November is the cheapest month in which you can book a flight from Key West to Portland, Maine (average of $170). Flying from Key West to Portland, Maine in February is currently the most expensive (average of $331). 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

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top 2 airlines flying from Key West to Portland

Discover the top 2 airlines that operate flights from Key West to Portland. 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 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$336FlexibilityNo cancel feeOn-time71%
DeltaCheapest$274Average$380FlexibilityNo cancel feeOn-timeN/A

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