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$189+ 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 8/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PWM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
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 June 18, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$189
(American Airlines)

Popular in

August

Cheapest in

July

Average price

$489
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. 9% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 10% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/16. 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 7/234:58 pmEYW - PWM
1 stop6h 21mAmerican Airlines
Wed 7/305:55 amPWM - EYW
1 stop7h 56mAmerican Airlines
Deal found 6/16$269
This Delta deal was found by Cheapflights users on 6/16. 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.
Wed 9/106:20 pmEYW - PWM
1 stop5h 43mDelta
Fri 9/196:30 amPWM - EYW
2 stops10h 42mDelta
Deal found 6/16$284
This FlightHub deal was found by Cheapflights users on 6/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2010:12 amEYW - PWM
1 stop25h 41mBreeze Airways
Sat 6/2812:38 pmPWM - EYW
1 stop24h 39mBreeze Airways
Deal found 6/17$659

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 June 18, 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

Wed 7/23

4:58 pm-11:19 pm

1 stop6h 21m

Portland

Wed 7/30

5:55 am-1:51 pm

1 stop7h 56m

$269

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/10

6:20 pm-12:03 am

1 stop5h 43m

Portland

Fri 9/19

6:30 am-5:12 pm

2 stops10h 42m

$284

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 9/10

9:47 am-1:51 pm

3 stops52h 04m

Portland

Fri 9/19

2:36 pm-10:19 am

3 stops43h 43m

$757

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 8/6

5:02 pm-10:59 pm

1 stop5h 57m

$189

Key WestPortland

EYW - PWM

EYWPWM

Key West

Wed 8/6

2:12 pm-5:37 pm

3 stops27h 25m

$602

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 18, 2025.
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Boarding

8.4

Crew

8.8

Food

6.8

Overall

8.1

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
182 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Boarding

8.4

Crew

8.8

Food

6.8

Overall

8.1

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,964 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Boarding

8.4

Crew

8.8

Food

6.8

Overall

8.1

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,809 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Boarding

8.4

Crew

8.8

Food

6.8

Overall

8.1

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
182 reviews

Entertainment

6.6

Boarding

8.4

Crew

8.8

Food

6.8

Overall

8.1

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

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

    According to our current data, American Airlines ($269), Delta ($284), and Breeze Airways ($757) offers the cheapest pricing from Key West to Portland, Maine. These flights start at 31% 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 Key West?

Book flights to Key West if you plan to visit one of these locations
North Conway
Bath
Brunswick
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 June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$336FlexibilityNo cancel feeOn-time71%

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