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Key West

$269+ Cheap flights from Portland, ME to Key West (PWM - EYW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Key West are usually found in June or August, booked 47 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 julio 3, 2025.

Round-trip from

$269
(American Airlines)

Popular in

March

Cheapest in

June

Average price

$373
From Portland to Key West
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($97 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 julio 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/2. 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.
mié. 8/138:05 amPWM - EYW
1 stop8h 41mAmerican Airlines
lun. 8/185:02 pmEYW - PWM
1 stop5h 57mAmerican Airlines
Deal found 7/2$269
This Delta deal was found by Cheapflights users on 7/3. 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.
sáb. 11/112:30 pmPWM - EYW
1 stop7h 14mDelta
mar. 11/46:00 pmEYW - PWM
1 stop6h 03mDelta
Deal found 7/3$348
This United Airlines deal was found by Cheapflights users on 7/3. 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.
sáb. 11/17:22 pmPWM - EYW
2 stops19h 47mUnited Airlines
mar. 11/43:05 pmEYW - PWM
3 stops22h 53mUnited Airlines
Deal found 7/3$617

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 julio 3, 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

mié. 8/13

8:05 am-4:46 pm

1 stop8h 41m

Key West

lun. 8/18

5:02 pm-10:59 pm

1 stop5h 57m

$269

PortlandKey West

PWM - EYW

PWMEYW

Portland

vie. 9/26

6:00 am-1:02 pm

1 stop7h 02m

Key West

lun. 9/29

6:10 pm-12:11 am

1 stop6h 01m

$426

PortlandKey West

PWM - EYW

PWMEYW

Portland

vie. 9/26

2:36 pm-10:19 am

3 stops43h 43m

Key West

lun. 9/29

12:32 pm-10:41 am

2 stops46h 09m

$715

PortlandKey West

PWM - EYW

PWMEYW

Portland

mié. 7/16

7:28 am-1:12 pm

1 stop5h 44m

Key West

dom. 7/20

1:42 pm-11:59 pm

2 stops34h 17m

$724

PortlandKey West

PWM - EYW

PWMEYW

Portland

mié. 7/16

12:38 pm-11:41 am

3 stops23h 03m

Key West

dom. 7/20

10:02 am-5:36 pm

2 stops31h 34m

$776

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 June 27, 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 47 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 $492). 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 julio 3, 2025.
Read through reviews of airlines operating flights from Portland to Key West, such as Breeze Airways, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Crew

8.8

Boarding

8.3

Overall

8.1

Entertainment

6.6

Food

6.8

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
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Crew

8.8

Boarding

8.3

Overall

8.1

Entertainment

6.6

Food

6.8

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
7,982 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Crew

8.8

Boarding

8.3

Overall

8.1

Entertainment

6.6

Food

6.8

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
8,861 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Crew

8.8

Boarding

8.3

Overall

8.1

Entertainment

6.6

Food

6.8

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
183 reviews

Comfort

8.2

Crew

8.8

Boarding

8.3

Overall

8.1

Entertainment

6.6

Food

6.8

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 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.

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

    American Airlines, at $269, 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 33% below the average price you’ll pay for this route.

  • 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 $492). 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$378FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$419FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$372Average$578FlexibilityNo cancel feeOn-time69%

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