$156+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — EYW
Oct 19 — Oct 261
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 September 19, 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 September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/116:31 pm -
1 stop16h 50m
Tue 11/171:16 pm -
1 stop28h 35m
Deal found 9/16![Breeze Airways logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Sun 11/83:10 pm -
1 stop26h 28m
Thu 11/128:54 pm -
1 stop12h 14m
Deal found 9/14![Multiple Airlines logo]()
$314
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/212:05 pm -
1 stop6h 20m
Wed 12/95:35 pm -
1 stop5h 22m
Deal found 9/16![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/212:28 pm -
2 stops22h 52m
Wed 12/910:45 am -
1 stop7h 47m
Deal found 9/16![Multiple Airlines logo]()
$336
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 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
Sat 11/1410:04 am -
1 stop7h 47m
Deal found 9/18![Breeze Airways logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 9/16. 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
Tue 11/171:16 pm -
1 stop28h 35m
Deal found 9/16![Breeze Airways logo]()
$353
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 11/142:05 pm -
1 stop5h 55m
Fri 11/207:25 am -
1 stop5h 36m
Deal found 9/18![Delta logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 12/45:35 pm -
2 stops16h 29m
Sun 12/67:22 pm -
1 stop13h 46m
Deal found 9/14![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 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
Sat 11/2110:04 am -
1 stop7h 47m
Deal found 9/18![Multiple Airlines logo]()
$369
This Kiwi.com deal was found by Cheapflights users on 9/16. 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
Sat 11/2110:04 am -
1 stop7h 47m
Deal found 9/16![Breeze Airways logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 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
Fri 11/2010:59 am -
1 stop22h 09m
Deal found 9/18![Multiple Airlines logo]()
$380
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 September 19, 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 September 19, 2026.
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/212:05 pm -
1 stop6h 20m
Wed 12/95:35 pm -
1 stop5h 22m
Deal found 9/16![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 9/18. 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.
Sat 11/142:05 pm -
1 stop5h 55m
Fri 11/207:25 am -
1 stop5h 36m
Deal found 9/18![Delta logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Fri 12/45:35 pm -
2 stops16h 29m
Sun 12/67:22 pm -
1 stop13h 46m
Deal found 9/14![Multiple Airlines logo]()
$362
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 10/246:00 am -
1 stop9h 24m
Wed 10/282:51 pm -
1 stop8h 30m
Deal found 9/14![United Airlines logo]()
$528
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/147:00 am -
2 stops9h 58m
Wed 10/214:45 pm -
1 stop5h 51m
Deal found 9/14![American Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 9/18. 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.
Sun 10/112:09 pm -
1 stop5h 52m
Sun 10/186:10 pm -
1 stop5h 25m
Deal found 9/18![Delta logo]()
$528
Last-minute flights from Portland to Key WestDiscover last-minute flight deals from Portland to Key West. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Key West. Data last updated September 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 9/305:09 pm -
2 stops17h 10m
Sun 10/410:59 am -
1 stop22h 09m
Deal found 9/15![Breeze Airways logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:19 pm -
2 stops41h 00m
Wed 10/2110:04 am -
1 stop7h 47m
Deal found 9/17![Breeze Airways logo]()
$391
This American Airlines deal was found by Cheapflights users on 9/14. 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 10/147:00 am -
2 stops9h 58m
Wed 10/214:45 pm -
1 stop5h 51m
Deal found 9/14![American Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:09 pm -
2 stops17h 10m
Sat 10/1710:04 am -
1 stop7h 47m
Deal found 9/17![Breeze Airways logo]()
$449
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:09 pm -
2 stops17h 10m
Mon 10/1911:59 am -
1 stop28h 25m
Deal found 9/17![Breeze Airways logo]()
$465
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:09 pm -
2 stops17h 10m
Sun 10/1810:59 am -
1 stop22h 09m
Deal found 9/17![Breeze Airways logo]()
$471
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/157:00 am -
2 stops28h 19m
Wed 10/2110:04 am -
1 stop7h 47m
Deal found 9/17![Breeze Airways logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:35 pm -
2 stops40h 44m
Fri 10/2310:59 am -
1 stop22h 09m
Deal found 9/17![Breeze Airways logo]()
$456
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:53 pm -
2 stops17h 31m
Wed 10/2110:04 am -
1 stop7h 47m
Deal found 9/17![Breeze Airways logo]()
$466
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:53 pm -
2 stops17h 31m
Sun 10/188:41 pm -
1 stop12h 27m
Deal found 9/17![Multiple Airlines logo]()
$492
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 am -
2 stops27h 19m
Sat 10/2410:04 am -
1 stop7h 47m
Deal found 9/17![Multiple Airlines logo]()
$440
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 September 19, 2026.
Search for one-way flight options from Portland to Key West. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:31 pm -
1 stop19h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/216:31 pm -
1 stop16h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Breeze Airways logo]()
$176
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:00 am -
3 stops28h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Breeze Airways logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 9/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:00 am -
2 stops29h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Multiple Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 11/216:31 pm -
3 stops39h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Multiple Airlines logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:10 pm -
1 stop19h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Multiple Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/157:00 am -
2 stops28h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Breeze Airways logo]()
$307
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 September 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $287 (Kiwi.com) |
One-way from | $156 (Kiwi.com) |
Popular in | August |
Cheapest in | September |
Average price | $300 |
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 September 19, 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
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 11/21
6:31 pm-11:21 am
1 stop16h 50m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$176
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 10/10
7:00 am-12:43 pm
2 stops29h 43m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$286
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 11/21
6:31 pm-10:19 am
3 stops39h 48m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$290
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Thu 11/19
3:10 pm-10:19 am
2 stops19h 09m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$318
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Wed 12/2
12:05 pm-6:25 pm
1 stop6h 20m
Key West
Wed 12/9
5:35 pm-10:57 pm
1 stop5h 22m
$321
Quickest round-trip
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sun 1/31
7:23 am-2:08 pm
1 stop6h 45m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$339
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 1/16
9:48 am-10:19 am
1 stop24h 31m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$340
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 10/10
6:31 pm-11:21 am
1 stop16h 50m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$356
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Sat 11/14
2:05 pm-8:00 pm
1 stop5h 55m
Key West
Fri 11/20
7:25 am-1:01 pm
1 stop5h 36m
$356
PortlandKey West
PWM Portland - EYW Key West
PWMEYW
Portland
Fri 12/4
5:35 pm-10:04 am
2 stops16h 29m
Key West
Sun 12/6
7:22 pm-9:08 am
1 stop13h 46m
$362
Showing 1-10 of 13 resultsSorted 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 September.
| 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
How far ahead should I book a flight from Portland, Maine to Key West?
To ensure you get the cheapest price possible for a flight from Portland, Maine to Key West, you should look to book at least 25 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, September is the cheapest month in which you can book a flight from Portland, Maine to Key West (average of $300). Flying from Portland, Maine to Key West in August is currently the most expensive (average of $834). 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.
How much does it cost to fly round-trip from Portland, Maine to Key West?
Airfare is below average for this route at the moment.
Portland, Maine to Key West flights typically cost between $326 and $368 in November.The cheapest round-trip price found within the last 5 days was $287 on Breeze Airways (Nov 11-Nov 17).
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 September 19, 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.
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Crew
8.5
Food
7.2
Boarding
8.1
Comfort
7.8
Overall
7.8
Entertainment
7.8
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.
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.
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Complete your trip
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Search flights from Portland to Key West by cabin class
Find flights from Portland to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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 September 19, 2026.
Portland and Key West flights
Browse other Portland and Key West flight options. Last updated on September 19, 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 September 19, 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 September 19, 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$484 | FlexibilityNo cancel fee | On-time71% |