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$242+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
ago. 26 — sep. 21
mar. 8/26
mar. 9/2
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 agosto 21, 2025.

Round-trip from

$269
(Delta)

One-way from

$242
(American Airlines)

Popular in

June

Cheapest in

November

Average price

$310
From Key West to Portland
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One-way flight from Key West to Portland
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Highest demand for flights based on searches. 13% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 21, 2025.

This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/236:10 pmEYW - PWM
1 stop6h 01mDelta
mar. 9/306:00 amPWM - EYW
1 stop7h 02mDelta
Deal found 8/21$269
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/242:00 pmEYW - PWM
2 stops10h 34mDelta
mar. 9/306:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$279
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:10 pmEYW - PWM
1 stop6h 01mDelta
mar. 9/306:00 amPWM - EYW
1 stop7h 02mDelta
Deal found 8/21$288
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:10 pmEYW - PWM
1 stop6h 01mDelta
mié. 10/111:34 amPWM - EYW
2 stops8h 33mDelta
Deal found 8/21$293
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/236:10 pmEYW - PWM
1 stop6h 01mDelta
vie. 9/266:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$300
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/242:00 pmEYW - PWM
2 stops10h 34mDelta
vie. 9/266:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$305
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/226:10 pmEYW - PWM
1 stop6h 01mDelta
vie. 9/266:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$312
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/236:10 pmEYW - PWM
1 stop6h 01mDelta
lun. 9/296:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$328
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/242:00 pmEYW - PWM
2 stops10h 34mDelta
lun. 9/296:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$333
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/196:10 pmEYW - PWM
1 stop6h 01mDelta
lun. 9/296:00 amPWM - EYW
2 stops11h 12mDelta
Deal found 8/21$347
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/236:10 pmEYW - PWM
1 stop6h 01mDelta
mié. 10/11:35 pmPWM - EYW
1 stop6h 32mDelta
Deal found 8/21$354

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 agosto 21, 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

jue. 9/25

6:10 pm-12:11 am

1 stop6h 01m

Portland

mar. 9/30

6:00 am-1:02 pm

1 stop7h 02m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

mar. 9/23

6:10 pm-12:11 am

1 stop6h 01m

Portland

mar. 9/30

6:00 am-1:02 pm

1 stop7h 02m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/24

6:10 pm-12:11 am

1 stop6h 01m

Portland

mar. 9/30

6:00 am-1:02 pm

1 stop7h 02m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

mié. 9/24

6:10 pm-12:11 am

1 stop6h 01m

Portland

mié. 10/1

11:34 am-8:07 pm

2 stops8h 33m

$274

Key WestPortland

EYW - PWM

EYWPWM

Key West

jue. 9/25

6:10 pm-12:11 am

1 stop6h 01m

Portland

mié. 10/1

6:00 am-5:12 pm

2 stops11h 12m

$274

Key WestPortland

EYW - PWM

EYWPWM

Key West

mar. 9/23

6:10 pm-12:11 am

1 stop6h 01m

Portland

mié. 10/1

11:34 am-8:07 pm

2 stops8h 33m

$274

Key WestPortland

EYW - PWM

EYWPWM

Key West

lun. 9/22

6:10 pm-12:11 am

1 stop6h 01m

Portland

mar. 9/30

6:00 am-1:02 pm

1 stop7h 02m

$288

Key WestPortland

EYW - PWM

EYWPWM

Key West

mar. 10/14

11:22 am-10:48 pm

2 stops11h 26m

$242

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

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, January is the cheapest month in which you can book a flight from Key West to Portland, Maine (average of $296). Flying from Key West to Portland, Maine in July is currently the most expensive (average of $394). 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 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 agosto 21, 2025.
Peruse reviews from past customers who have flown with 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.
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
10,000 reviews
American Airlines
7.2
Good
10,000 reviews

Food

6.5

Boarding

7.5

Comfort

7.2

Entertainment

6.9

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 6h 01m. The distance between Key West and Portland, Maine is about 1468 mi.

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

    According to our current data, American Airlines ($258), offers the cheapest pricing from Key West to Portland, Maine. This flight start at 30% 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, January is the cheapest month in which you can book a flight from Key West to Portland, Maine (average of $296). Flying from Key West to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top airline flying from Key West to Portland

Discover the top airline 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 agosto 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$336FlexibilityNo cancel feeOn-time71%

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