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Key West

$164+ 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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in June or October, booked 90 days in advance, depart on a Tuesday or Wednesday and return on a Monday

Cheap 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 September 11, 2025.

Round-trip from

$269
(Delta)

One-way from

$164
(Delta)

Popular in

March

Cheapest in

June

Average price

$372
From Portland to Key West
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One-way flight from Portland to Key West
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Highest demand for flights based on searches. 18% potential increase in price ($90 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 10/286:00 amPWM - EYW
1 stop5h 27mDelta
Mon 11/31:57 pmEYW - PWM
1 stop8h 22mDelta
Deal found 9/11$269
This Delta deal was found by Cheapflights users on 9/11. 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 10/285:42 amPWM - EYW
2 stops11h 30mDelta
Sat 11/17:40 amEYW - PWM
2 stops8h 23mDelta
Deal found 9/11$279
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Mon 12/86:05 pmPWM - EYW
2 stops17h 00mMultiple Airlines
Fri 12/123:54 pmEYW - PWM
1 stop25h 44mMultiple Airlines
Deal found 9/9$287
This American Airlines deal was found by Cheapflights users on 9/9. 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 11/207:02 amPWM - EYW
2 stops12h 21mAmerican Airlines
Mon 11/245:09 pmEYW - PWM
1 stop6h 32mAmerican Airlines
Deal found 9/9$299
This American Airlines deal was found by Cheapflights users on 9/11. 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 11/117:02 amPWM - EYW
1 stop5h 41mAmerican Airlines
Sat 11/152:36 pmEYW - PWM
1 stop7h 56mAmerican Airlines
Deal found 9/11$309
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Thu 10/163:15 pmPWM - EYW
1 stop28h 40mMultiple Airlines
Fri 10/248:55 amEYW - PWM
1 stop25h 41mMultiple Airlines
Deal found 9/9$316
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/187:37 pmPWM - EYW
2 stops36h 38mMultiple Airlines
Sat 10/2510:47 amEYW - PWM
1 stop6h 51mMultiple Airlines
Deal found 9/9$322
This American Airlines deal was found by Cheapflights users on 9/11. 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.
Mon 10/276:00 amPWM - EYW
1 stop7h 52mAmerican Airlines
Sun 11/25:31 pmEYW - PWM
1 stop6h 28mAmerican Airlines
Deal found 9/11$323

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 September 11, 2025.
Use the filters below to find and compare flights from Portland to Key West that are best for you.

Fly from

Portland

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 10/28

6:00 am-11:27 am

1 stop5h 27m

Key West

Mon 11/3

1:57 pm-10:19 pm

1 stop8h 22m

$269

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 12/10

12:23 pm-7:34 pm

2 stops7h 11m

Key West

Wed 12/17

5:29 pm-11:37 pm

1 stop6h 08m

$274

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 10/28

5:42 am-5:12 pm

2 stops11h 30m

Key West

Sat 11/1

7:40 am-4:03 pm

2 stops8h 23m

$279

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 11/20

7:02 am-7:23 pm

2 stops12h 21m

Key West

Mon 11/24

4:10 pm-11:41 pm

2 stops7h 31m

$304

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 11/11

7:02 am-12:43 pm

1 stop5h 41m

Key West

Sat 11/15

2:36 pm-10:32 pm

1 stop7h 56m

$309

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 10/27

6:00 am-1:52 pm

1 stop7h 52m

Key West

Sun 11/2

5:31 pm-11:59 pm

1 stop6h 28m

$323

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 10/27

6:00 am-11:27 am

1 stop5h 27m

Key West

Mon 11/3

1:57 pm-10:19 pm

1 stop8h 22m

$324

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 11/1

1:27 pm-8:06 pm

1 stop6h 39m

$164

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 11/1

1:42 pm-9:56 pm

2 stops8h 14m

$252

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 10/8

5:42 am-5:21 pm

2 stops11h 39m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 12 results
1
2

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 August 29, 2025.

To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 38 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, August is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $328). Flying from Portland, Maine to Key West in March is currently the most expensive (average of $491). 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 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 September 11, 2025.
Read through reviews of airlines operating flights from Portland to Key West, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,960 reviews

Crew

8.5

Overall

8.0

Entertainment

7.9

Comfort

7.9

Food

7.3

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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?

    Delta and American Airlines can get you from Portland, Maine to Key West in just under 5h 27m. Your travel time can differ by up to 1h 44m. 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?

    American Airlines, at $268, was found to be the cheapest airline from Portland, Maine to Key West.Alternate airlines to your destination round-trip include Delta and United Airlines. American Airlines is currently priced 34% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Portland, Maine to Key West one-way?

    $164 is the cheapest one-way deal found within the past few days, from Delta. You may also be able to find cheap deals on American Airlines and United Airlines, with prices starting from $252 and $415, respectively.

  • 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, August is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $328). Flying from Portland, Maine to Key West in March is currently the most expensive (average of $491). 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$432FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$384FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$372Average$578FlexibilityNo cancel feeOn-time69%

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