HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Key West

$142+ 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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 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 August 18, 2025.

Round-trip from

$269
(American Airlines)

One-way from

$142
(American Airlines)

Popular in

March

Cheapest in

June

Average price

$370
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 ($91 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 18, 2025.

This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:00 amPWM - EYW
1 stop6h 58mAmerican Airlines
Wed 10/84:58 pmEYW - PWM
1 stop5h 50mAmerican Airlines
Deal found 8/17$283
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/205:41 amPWM - EYW
2 stops10h 58mAmerican Airlines
Mon 11/245:09 pmEYW - PWM
1 stop6h 29mAmerican Airlines
Deal found 8/17$293
This Delta deal was found by Cheapflights users on 8/18. 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.
Mon 10/276:00 amPWM - EYW
1 stop7h 02mDelta
Thu 10/301:57 pmEYW - PWM
1 stop8h 22mDelta
Deal found 8/18$307
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:00 amPWM - EYW
2 stops6h 58mAmerican Airlines
Fri 8/295:02 pmEYW - PWM
1 stop5h 57mAmerican Airlines
Deal found 8/17$312
This American Airlines deal was found by Cheapflights users on 8/17. 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 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 stop6h 03mAmerican Airlines
Sat 11/1512:40 pmEYW - PWM
2 stops9h 04mAmerican Airlines
Deal found 8/17$314

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 August 18, 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

Fri 1/9

5:51 am-1:55 pm

1 stop8h 04m

Key West

Wed 1/14

3:09 pm-10:31 pm

1 stop7h 22m

$269

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 10/7

6:00 am-12:58 pm

1 stop6h 58m

Key West

Wed 10/8

4:58 pm-10:48 pm

1 stop5h 50m

$283

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 12/11

5:53 am-1:46 pm

1 stop7h 53m

Key West

Mon 12/15

5:19 pm-10:29 pm

1 stop5h 10m

$288

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 11/20

5:41 am-4:39 pm

2 stops10h 58m

Key West

Mon 11/24

5:09 pm-11:38 pm

1 stop6h 29m

$293

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 10/7

6:00 am-12:58 pm

1 stop6h 58m

$142

PortlandKey West

PWM - EYW

PWMEYW

Portland

Tue 10/7

8:00 am-2:29 pm

1 stop6h 29m

$196

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 11/20

5:41 am-4:39 pm

2 stops10h 58m

$242

PortlandKey West

PWM - EYW

PWMEYW

Portland

Thu 11/20

6:00 am-2:04 pm

1 stop8h 04m

$277

PortlandKey West

PWM - EYW

PWMEYW

Portland

Fri 11/21

5:41 am-4:12 pm

2 stops10h 31m

$300

PortlandKey West

PWM - EYW

PWMEYW

Portland

Sat 11/29

6:00 am-12:44 pm

1 stop6h 44m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/17

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 8, 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 $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 August 18, 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
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
8,925 reviews
Delta
8.0
Very good
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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
7,981 reviews

Overall

8.0

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Crew

8.5

Food

7.3

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?

    American Airlines can get you from Portland, Maine to Key West in just under 8h 04m. Your travel time can differ by up to . Airlines will cover a distance of 1468 mi.

  • 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.

  • 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

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 Orlando flights
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Tampa flights
Boston to West Palm Beach flights
Boston to Fort Myers flights
Boston to Jacksonville flights
Boston to Key West flights
Boston to Sarasota flights
Boston to Orlando Sanford Intl flights
Portland to Orlando flights
Boston to St Petersburg flights
Boston to Pensacola flights
Boston to Melbourne flights
Portland to Fort Lauderdale flights
Bangor to Orlando flights
Boston to Panama City flights
Boston to Daytona Beach flights
Boston to Gainesville flights
Portland to Miami flights
Bangor to Orlando Sanford Intl flights
Portland to West Palm Beach flights
Portland to Jacksonville flights
Bangor to Miami flights
Portland to Tampa flights
Portland to Fort Myers flights
Boston to Valparaiso flights
Portland to Pensacola flights
Portland to Sarasota flights
Boston to Tallahassee flights
Bangor to Tampa flights
Portland to Panama City flights
Bangor to Fort Lauderdale flights
Portland to Valparaiso flights
Bangor to West Palm Beach flights
Augusta to Orlando flights
Bangor to Fort Myers flights
Boston to Punta Gorda flights
Portland to Melbourne flights
Bangor to Jacksonville flights
Bangor to St Petersburg flights
Bangor to Key West flights
Portland to Daytona Beach flights
Bangor to Sarasota flights
Augusta to Fort Myers flights
Rockland to Orlando flights
Bangor to Pensacola flights
Bar Harbor to West Palm Beach flights
Bangor to Melbourne 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$268Average$430FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$386FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$372Average$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.