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$188+ 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 5/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Mar 24 — Mar 311
Tue 3/24
Tue 3/31
1 adult, Economy
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Cheap 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 February 22, 2026.

This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:04 pm
EYW
-
PWM
1 stop5h 55m
American Airlines
Wed 3/1112:44 pm
PWM
-
EYW
2 stops9h 53m
American Airlines
Deal found 2/19$332
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:00 am
EYW
-
PWM
1 stop8h 14m
United Airlines
Sun 3/85:45 am
PWM
-
EYW
1 stop9h 10m
United Airlines
Deal found 2/19$339
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/44:52 pm
EYW
-
PWM
1 stop6h 28m
United Airlines
Mon 3/96:00 am
PWM
-
EYW
1 stop7h 23m
United Airlines
Deal found 2/19$348
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:00 am
EYW
-
PWM
1 stop6h 52m
United Airlines
Sat 9/56:00 am
PWM
-
EYW
1 stop9h 06m
United Airlines
Deal found 2/19$378
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:19 pm
EYW
-
PWM
1 stop6h 31m
American Airlines
Mon 3/96:00 am
PWM
-
EYW
2 stops9h 57m
American Airlines
Deal found 2/19$445

Find 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 February 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$332
(American Airlines)

One-way from

$188
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$368
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Portland flights.
Search Deals
From Key West to Portland
Search Deals
One-way flight from Key West to Portland
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 22, 2026.
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

Wed 3/4

5:04 pm-10:59 pm

1 stop5h 55m

Portland

Wed 3/11

12:44 pm-10:37 pm

2 stops9h 53m

$332

Key WestPortland

EYW - PWM

EYWPWM

Key West

Fri 3/6

7:00 am-3:14 pm

1 stop8h 14m

Portland

Sun 3/8

5:45 am-2:55 pm

1 stop9h 10m

$339

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 3/4

4:52 pm-11:20 pm

1 stop6h 28m

Portland

Mon 3/9

6:00 am-1:23 pm

1 stop7h 23m

$348

Key WestPortland

EYW - PWM

EYWPWM

Key West

Thu 4/2

4:40 pm-10:50 pm

1 stop6h 10m

Portland

Mon 4/6

7:00 am-1:45 pm

1 stop6h 45m

$406

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 5/6

11:46 am-7:16 pm

2 stops31h 30m

$188

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 5/6

11:46 am-7:16 pm

3 stops31h 30m

$188

Key WestPortland

EYW - PWM

EYWPWM

Key West

Mon 5/4

12:06 pm-4:16 pm

3 stops52h 10m

$216

Key WestPortland

EYW - PWM

EYWPWM

Key West

Tue 5/5

2:49 pm-11:29 pm

1 stop8h 40m

$270

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 5/6

4:20 pm-10:46 pm

1 stop6h 26m

$270

Key WestPortland

EYW - PWM

EYWPWM

Key West

Mon 3/16

2:35 pm-10:17 am

2 stops43h 42m

$273

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/18

Showing 1-10 of 12 results
1
2
  • 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 May is currently the most expensive (average of $321). 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 February 22, 2026.
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
7.9
Good
8,241 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

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
7.9
Good
8,241 reviews
Delta
7.9
Good
8,241 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

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
11,338 reviews
Delta
7.9
Good
8,241 reviews

Overall

7.9

Comfort

7.9

Food

7.2

Entertainment

7.8

Boarding

8.1

Crew

8.5

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 5h 55m. 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.

  • 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 May is currently the most expensive (average of $321). 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 February 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$319FlexibilityNo cancel feeOn-time71%
DeltaCheapest$274Average$353FlexibilityNo cancel feeOn-timeN/A

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