$162+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Dec 4 — Dec 111
Round-trip
1 adult, Economy
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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.Cheap flight deals from Portland to Key West
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to Key WestExplore 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 November 4, 2026.
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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:50 am -
1 stop8h 02m
Wed 12/212:05 pm -
2 stops11h 19m
Deal found 11/1![United Airlines logo]()
$365
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/211:57 am -
1 stop6h 30m
Sat 12/125:32 pm -
1 stop5h 47m
Deal found 11/1![American Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 11/1. 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.
Sat 11/286:00 am -
1 stop6h 59m
Tue 12/156:06 pm -
1 stop5h 27m
Deal found 11/1![Delta logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/146:31 pm -
1 stop16h 50m
Wed 11/1810:04 am -
1 stop7h 47m
Deal found 10/30![Breeze Airways logo]()
$402
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 11/252:05 pm -
1 stop5h 55m
Wed 12/26:06 pm -
1 stop5h 27m
Deal found 11/1![Delta logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:31 pm -
1 stop16h 50m
Sun 11/2210:59 am -
1 stop22h 09m
Deal found 11/1![Breeze Airways logo]()
$408
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 12/65:00 am -
1 stop7h 33m
Sat 12/125:32 pm -
1 stop5h 47m
Deal found 11/1![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 11/285:45 am -
1 stop6h 52m
Tue 12/155:32 pm -
1 stop5h 47m
Deal found 11/2![American Airlines logo]()
$441
Best flights from Portland to Key WestDiscover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
Discover carefully curated flight deals from Portland to Key West that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 4, 2026.
This Delta deal was found by Cheapflights users on 10/30. 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.
Wed 2/246:00 am -
2 stops11h 11m
Wed 3/36:00 pm -
1 stop5h 23m
Deal found 10/30![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 1/126:17 am -
1 stop6h 28m
Wed 1/207:30 am -
2 stops8h 56m
Deal found 11/3![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 11/3. 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.
Tue 1/196:17 am -
2 stops9h 47m
Sat 1/235:00 pm -
1 stop6h 26m
Deal found 11/3![Delta logo]()
$346
This Delta deal was found by Cheapflights users on 10/31. 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.
Wed 1/136:17 am -
2 stops9h 47m
Wed 1/205:00 pm -
1 stop6h 26m
Deal found 10/31![Delta logo]()
$346
Last-minute flights from Portland to Key WestDiscover last-minute flight deals from Portland to Key West. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Key West. Data last updated November 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/146:31 pm -
1 stop16h 50m
Wed 11/1810:04 am -
1 stop7h 47m
Deal found 10/30![Breeze Airways logo]()
$402
This Kiwi.com deal was found by Cheapflights users on 11/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:31 pm -
1 stop16h 50m
Sun 11/2210:59 am -
1 stop22h 09m
Deal found 11/1![Breeze Airways logo]()
$408
This United Airlines deal was found by Cheapflights users on 11/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:50 am -
1 stop8h 02m
Wed 12/212:05 pm -
2 stops11h 19m
Deal found 11/1![United Airlines logo]()
$365
This Delta deal was found by Cheapflights users on 11/1. 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.
Wed 11/252:05 pm -
1 stop5h 55m
Wed 12/26:06 pm -
1 stop5h 27m
Deal found 11/1![Delta logo]()
$406
This Delta deal was found by Cheapflights users on 11/1. 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.
Sat 11/286:00 am -
1 stop6h 59m
Tue 12/156:06 pm -
1 stop5h 27m
Deal found 11/1![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 11/4. 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.
Sat 11/285:45 am -
1 stop6h 52m
Tue 12/155:32 pm -
1 stop5h 47m
Deal found 11/4![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Wed 12/211:57 am -
1 stop6h 30m
Sat 12/125:32 pm -
1 stop5h 47m
Deal found 11/1![American Airlines logo]()
$391
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 12/65:00 am -
1 stop7h 33m
Sat 12/125:32 pm -
1 stop5h 47m
Deal found 11/1![American Airlines logo]()
$418
One-way flights from Portland to Key WestSearch for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
Search for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/165:35 pm -
2 stops19h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Breeze Airways logo]()
$162
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Sat 1/169:20 am -
1 stop6h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/145:09 pm -
2 stops17h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Breeze Airways logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:09 pm -
1 stop17h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Breeze Airways logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 11/146:31 pm -
1 stop14h 33m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/105:09 pm -
3 stops38h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Multiple Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 11/1. 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.
Sun 1/315:00 am -
1 stop7h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$364
This Delta deal was found by Cheapflights users on 11/3. 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 1/316:00 am -
2 stops10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Delta logo]()
$369
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 November 4, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $294 (Kiwi.com) |
One-way from | $162 (Kiwi.com) |
Popular in | August |
Cheapest in | September |
Average price | $427 |
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 7,457,451 searches. Data last updated November 4, 2026.
Use the filters below to find and compare flights from Portland to Key West that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 1/16
9:20 am-4:09 pm
1 stop6h 49m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$171
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 11/14
5:09 pm-10:19 am
2 stops17h 10m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$229
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Mon 11/16
5:35 pm-12:42 pm
3 stops43h 07m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$262
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 11/14
5:09 pm-11:04 am
3 stops41h 55m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$324
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Tue 11/10
5:09 pm-8:04 am
3 stops38h 55m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$333
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Wed 2/24
6:00 am-5:11 pm
2 stops11h 11m
Key West
Wed 3/3
6:00 pm-11:23 pm
1 stop5h 23m
$346
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Tue 1/12
6:17 am-12:45 pm
1 stop6h 28m
Key West
Wed 1/20
7:30 am-4:26 pm
2 stops8h 56m
$346
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Tue 1/19
6:17 am-4:04 pm
2 stops9h 47m
Key West
Sat 1/23
5:00 pm-11:26 pm
1 stop6h 26m
$346
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Wed 1/13
6:17 am-4:04 pm
2 stops9h 47m
Key West
Wed 1/20
5:00 pm-11:26 pm
1 stop6h 26m
$346
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sun 1/31
5:00 am-12:18 pm
1 stop7h 18m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$364
Sorted by cheapest first
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
PWM-EYW
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
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 November 4, 2026.
Read through reviews of airlines operating flights from Portland to Key West, such as Delta,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Overall
7.8
Food
7.2
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
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Complete your trip
Complete your trip to Key West by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Portland to Key West by cabin class
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Other flights to Key West
Explore flights to Key West departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
Portland and Key West flights
Browse other Portland and Key West flight options. Last updated on November 4, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on November 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$256 | Average$447 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$256 | Average$534 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$472 | FlexibilityNo cancel fee | On-time71% |