HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$179+ 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 5/12. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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.

The best prices from Portland to Key West are usually found in August or December, 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 March 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(American Airlines)

One-way from

$179
(Delta)

Popular in

May

Cheapest in

August

Average price

$570
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. 18% potential increase in price ($94 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

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 March 3, 2025.

This American Airlines deal was found by Cheapflights users on 3/1. 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 3/257:20 amPWM - EYW
2 stops11h 29mAmerican Airlines
Tue 4/15:24 pmEYW - PWM
1 stop5h 20mAmerican Airlines
Deal found 3/1$274
This Delta deal was found by Cheapflights users on 3/1. 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 3/256:15 amPWM - EYW
1 stop6h 35mDelta
Tue 4/16:15 pmEYW - PWM
1 stop5h 43mDelta
Deal found 3/1$294
This United Airlines deal was found by Cheapflights users on 3/3. 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.
Tue 3/116:00 amPWM - EYW
1 stop9h 03mUnited Airlines
Mon 3/1710:19 amEYW - PWM
2 stops12h 56mUnited Airlines
Deal found 3/3$354

Find flights from Portland to Key West within your budget

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 March 3, 2025.

Fly from

Portland

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/25

7:20 am-6:49 pm

2 stops11h 29m

Key West

Tue 4/1

5:24 pm-10:44 pm

1 stop5h 20m

$274

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 3/25

6:15 am-12:50 pm

1 stop6h 35m

Key West

Tue 4/1

6:15 pm-11:58 pm

1 stop5h 43m

$294

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 5/12

6:00 am-1:03 pm

1 stop7h 03m

Key West

Sat 5/17

10:55 am-11:23 pm

2 stops12h 28m

$415

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 5/12

1:30 pm-7:36 pm

1 stop6h 06m

$179

PortlandKey West

PWM - EYW

PWMEYW

Portland

Mon 5/12

7:45 am-6:49 pm

2 stops11h 04m

$184

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

5:40 am-9:15 am

2 stops27h 35m

$330

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 7/3

5:14 am-1:41 pm

3 stops32h 27m

$959

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Key West flight deals on Cheapflights vs. FlightHub >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 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 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.

Travel insights for flights from Portland to Key West

Get recent, data-driven insights about flights from Portland to Key West including ideal travel times, pricing trends, and more.

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 February 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 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 $503). 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.

What is the cheapest time of day to fly from PWM to EYW?

Find hourly flight availability from Portland to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 3, 2025.

It’s typically best to fly out from Portland, Maine to Key West in the morning. Doing so could potentially save you 13% on the flight price compared to flying at noon, which is usually more expensive.

Rainfall in Key West by month

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

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

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

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

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 March 3, 2025.
Read through reviews of airlines operating flights from Portland to Key West, such as Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,713 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,713 reviews
Alaska Airlines
8.0
Very good
9,713 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,070 reviews
Alaska Airlines
8.0
Very good
9,713 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,679 reviews
Alaska Airlines
8.0
Very good
9,713 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,713 reviews

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $274, 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 36% 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?

    $179 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 $184 and $330, 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 $503). 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 Jacksonville flights
Boston to Sarasota flights
Boston to Key West flights
Portland to Orlando flights
Boston to Pensacola flights
Boston to Daytona Beach flights
Boston to Orlando Sanford Intl flights
Boston to Panama City flights
Boston to Melbourne flights
Portland to Miami flights
Portland to Tampa flights
Portland to West Palm Beach flights
Boston to St Petersburg flights
Portland to Fort Myers flights
Portland to Fort Lauderdale flights
Boston to Valparaiso flights
Boston to Gainesville flights
Bangor to Orlando flights
Bangor to Orlando Sanford Intl flights
Portland to Jacksonville flights
Boston to Tallahassee flights
Bangor to Tampa flights
Bangor to Miami flights
Portland to Daytona Beach flights
Portland to Sarasota flights
Bangor to St Petersburg flights
Portland to Panama City flights
Bangor to Jacksonville flights
Bangor to Sarasota flights
Bangor to Fort Lauderdale flights
Portland to Pensacola flights
Bangor to Pensacola flights
Boston to Punta Gorda flights
Portland to Melbourne flights
Bangor to West Palm Beach flights
Bangor to Fort Myers flights
Bangor to Daytona Beach flights
Augusta to Tampa flights
Augusta to Fort Myers flights
Portland to Valparaiso flights
Boston to Valdosta flights
Augusta to Orlando flights
Rockland to Fort Myers 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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$246Average$430FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$268Average$431FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$345Average$588FlexibilityNo 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.