HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$134+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Key West with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Key West are usually found in June or August, booked 26 days in advance, depart on a Tuesday or Wednesday and return on a Monday

Cheap 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 December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:18 pmPWM - EYW
1 stop16h 01mBreeze Airways
Thu 12/188:55 amEYW - PWM
1 stop24h 11mBreeze Airways
Deal found 12/3$280
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:18 pmPWM - EYW
1 stop16h 01mBreeze Airways
Fri 12/191:10 pmEYW - PWM
1 stop21h 26mBreeze Airways
Deal found 12/3$302
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:05 pmPWM - EYW
2 stops17h 00mBreeze Airways
Thu 12/188:55 amEYW - PWM
1 stop24h 11mBreeze Airways
Deal found 12/3$310
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1711:16 amPWM - EYW
1 stop20h 59mBreeze Airways
Fri 12/191:10 pmEYW - PWM
1 stop21h 26mBreeze Airways
Deal found 12/3$314
This American Airlines deal was found by Cheapflights users on 12/2. 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.
Thu 12/115:34 amPWM - EYW
2 stops11h 23mAmerican Airlines
Tue 12/161:45 pmEYW - PWM
1 stop7h 52mAmerican Airlines
Deal found 12/2$332
This Delta deal was found by Cheapflights users on 12/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:15 amPWM - EYW
2 stops11h 00mDelta
Tue 12/163:02 pmEYW - PWM
2 stops8h 19mDelta
Deal found 12/2$337
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:18 pmPWM - EYW
1 stop16h 01mMultiple Airlines
Thu 12/1812:20 pmEYW - PWM
2 stops20h 46mMultiple Airlines
Deal found 12/3$339
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:18 pmPWM - EYW
1 stop16h 01mBreeze Airways
Wed 12/1710:47 amEYW - PWM
1 stop6h 51mBreeze Airways
Deal found 12/3$340
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/136:18 pmPWM - EYW
1 stop16h 01mMultiple Airlines
Sat 12/202:30 pmEYW - PWM
2 stops42h 36mMultiple Airlines
Deal found 12/3$345
This Delta deal was found by Cheapflights users on 12/3. 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.
Sun 12/146:08 amPWM - EYW
1 stop7h 59mDelta
Wed 12/173:02 pmEYW - PWM
1 stop7h 21mDelta
Deal found 12/3$367
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:05 pmPWM - EYW
2 stops17h 00mBreeze Airways
Wed 12/1710:47 amEYW - PWM
1 stop6h 51mBreeze Airways
Deal found 12/3$370

Find 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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$219
(American Airlines)

One-way from

$134
(Kiwi.com)

Popular in

March

Cheapest in

June

Average price

$477
Provider with most accurate pricing for Portland-Key West flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Key West flights.
Search Deals
From Portland to Key West
Search Deals
One-way flight from Portland to Key West
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($74 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 4, 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

Wed 1/28

12:40 pm-9:47 pm

2 stops9h 07m

Key West

Tue 2/3

5:21 pm-11:43 pm

1 stop6h 22m

$224

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 1/13

5:30 am-1:48 pm

1 stop8h 18m

Key West

Wed 1/21

7:10 am-5:16 pm

2 stops10h 06m

$224

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 1/28

6:00 am-12:48 pm

1 stop6h 48m

Key West

Tue 2/3

2:45 pm-10:27 pm

1 stop7h 42m

$277

PortlandKey West

PWM - EYW

PWMEYW

Portland

Wed 1/14

12:46 pm-11:56 pm

2 stops11h 10m

Key West

Sat 1/24

6:06 am-3:31 pm

2 stops9h 25m

$280

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 1/24

6:00 am-5:05 pm

2 stops11h 05m

Key West

Sat 1/31

12:00 pm-9:37 pm

2 stops9h 37m

$314

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sun 12/21

6:00 am-2:13 pm

1 stop8h 13m

Key West

Fri 12/26

3:09 pm-11:22 pm

1 stop8h 13m

$367

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 2/17

5:31 am-12:02 pm

1 stop6h 31m

Key West

Wed 2/18

5:10 pm-11:17 pm

1 stop6h 07m

$367

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 12/15

6:05 pm-11:05 am

2 stops17h 00m

Key West

Wed 12/17

10:47 am-5:38 pm

1 stop6h 51m

$370

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 2/7

6:18 pm-10:21 am

1 stop16h 03m

$134

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 2/7

12:46 pm-11:56 pm

2 stops11h 10m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 11 results
1
2

Compare providers for flights from Portland to Key West

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Key West in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland, Maine-Key West flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Key West flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Portland, Maine-Key West flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Key West flights, Cheapflights users trust eDreams the most. eDreams 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 Portland, Maine-Key West 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 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 November 28, 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 26 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, May is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $179). Flying from Portland, Maine to Key West in April is currently the most expensive (average of $292). 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 December 4, 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
7.9
Good
8,011 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,011 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,066 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,047 reviews
Delta
7.9
Good
8,011 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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?

    American Airlines and Delta can get you from Portland, Maine to Key West in just under 8h 18m. Your travel time can differ by up to 49m. 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?

    Delta, at $256, was found to be the cheapest airline from Portland, Maine to Key West.Alternate airlines to your destination round-trip include American Airlines and United Airlines. Delta is currently priced 39% 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, May is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $179). Flying from Portland, Maine to Key West in April is currently the most expensive (average of $292). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Key West

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Orlando flights
Boston to Tampa flights
Boston to West Palm Beach flights
Boston to Fort Myers flights
Boston to Sarasota flights
Boston to Key West flights
Boston to Jacksonville flights
Boston to Daytona Beach flights
Boston to St Petersburg flights
Portland to Orlando flights
Boston to Orlando Sanford Intl flights
Boston to Pensacola flights
Portland to Tampa flights
Portland to Fort Lauderdale flights
Portland to Miami flights
Portland to Fort Myers flights
Boston to Panama City flights
Boston to Valparaiso flights
Portland to West Palm Beach flights
Portland to Sarasota flights
Bangor to Orlando flights
Portland to Jacksonville flights
Bangor to Miami flights
Bangor to Orlando Sanford Intl flights
Bangor to Fort Lauderdale flights
Boston to Melbourne flights
Bangor to Jacksonville flights
Bangor to Fort Myers flights
Boston to Gainesville flights
Boston to Punta Gorda flights
Portland to Melbourne flights
Augusta to Fort Myers flights
Boston to Tallahassee flights
Bangor to Sarasota flights
Bangor to West Palm Beach flights
Bangor to Tampa flights
Bangor to St Petersburg flights
Rockland to Fort Myers flights
Portland to Pensacola flights
Augusta to Tampa flights
Portland to Valparaiso flights
Bangor to Melbourne flights
Bangor to Pensacola flights
Portland to Panama City flights
Bangor to Key West flights
Portland to Daytona Beach flights
Augusta to Orlando flights

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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$439FlexibilityNo cancel feeOn-time71%
DeltaCheapest$268Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$373Average$578FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.