$163+ Cheap flights from Key West to Portland (EYW - PDX)
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 4/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Apr 21 — Apr 281
Round-trip
1 adult, Economy
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Cheapest flights from Key West to PortlandExplore the most affordable flight options available from Key West to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
Explore the most affordable flight options available from Key West to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/309:58 am
EYW
- PDX
2 stops52h 44m
Multiple Airlines
Thu 5/282:44 pm
PDX
- EYW
1 stop17h 18m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 3/18. 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.
Wed 4/222:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Sun 4/266:28 am
PDX
- EYW
1 stop10h 12m
Delta
Deal found 3/18![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/20. 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 5/1411:48 am
EYW
- PDX
2 stops13h 14m
Delta
Sat 5/235:51 pm
PDX
- EYW
2 stops14h 02m
Delta
Deal found 3/20![Delta logo]()
$399
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 4/232:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Mon 4/2712:30 am
PDX
- EYW
2 stops13h 53m
Delta
Deal found 3/18![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops24h 15m
Delta
Sat 5/210:55 pm
PDX
- EYW
1 stop8h 15m
Delta
Deal found 3/18![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 4/232:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Mon 4/2711:06 pm
PDX
- EYW
1 stop8h 40m
Delta
Deal found 3/18![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops18h 41m
Delta
Sun 4/266:05 pm
PDX
- EYW
2 stops13h 41m
Delta
Deal found 3/18![Delta logo]()
$442
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Fri 4/33:56 pm
EYW
- PDX
1 stop11h 26m
American Airlines
Sun 4/55:40 am
PDX
- EYW
1 stop7h 44m
American Airlines
Deal found 3/17![American Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops24h 15m
Delta
Mon 4/2711:06 pm
PDX
- EYW
1 stop8h 40m
Delta
Deal found 3/18![Delta logo]()
$462
Best flights from Key West to PortlandDiscover carefully curated flight deals from Key West to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
Discover carefully curated flight deals from Key West to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/21. 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 4/309:58 am
EYW
- PDX
2 stops52h 44m
Multiple Airlines
Thu 5/282:44 pm
PDX
- EYW
1 stop17h 18m
Multiple Airlines
Deal found 3/21![Multiple Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 3/18. 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.
Wed 4/222:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Sun 4/266:05 pm
PDX
- EYW
2 stops13h 41m
Delta
Deal found 3/18![Delta logo]()
$394
This American Airlines deal was found by Cheapflights users on 3/19. 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 5/142:29 pm
EYW
- PDX
1 stop10h 09m
American Airlines
Sat 5/2310:59 pm
PDX
- EYW
2 stops11h 06m
American Airlines
Deal found 3/19![American Airlines logo]()
$414
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 5/1411:48 am
EYW
- PDX
2 stops13h 14m
Delta
Sat 5/235:18 pm
PDX
- EYW
2 stops14h 35m
Delta
Deal found 3/18![Delta logo]()
$399
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Fri 4/33:56 pm
EYW
- PDX
1 stop11h 26m
American Airlines
Sun 4/55:40 am
PDX
- EYW
1 stop7h 44m
American Airlines
Deal found 3/17![American Airlines logo]()
$449
Last-minute flights from Key West to PortlandDiscover last-minute flight deals from Key West to Portland. Data last updated March 22, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Portland. Data last updated March 22, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/17. 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.
Fri 4/33:56 pm
EYW
- PDX
1 stop11h 26m
American Airlines
Sun 4/55:40 am
PDX
- EYW
1 stop7h 44m
American Airlines
Deal found 3/17![American Airlines logo]()
$449
This American Airlines deal was found by Cheapflights users on 3/20. 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 4/44:20 pm
EYW
- PDX
1 stop11h 02m
American Airlines
Mon 4/1310:23 pm
PDX
- EYW
1 stop9h 53m
American Airlines
Deal found 3/20![American Airlines logo]()
$467
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops24h 15m
Delta
Sat 5/210:55 pm
PDX
- EYW
1 stop8h 15m
Delta
Deal found 3/18![Delta logo]()
$437
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops18h 41m
Delta
Sun 4/266:05 pm
PDX
- EYW
2 stops13h 41m
Delta
Deal found 3/18![Delta logo]()
$442
This Delta deal was found by Cheapflights users on 3/18. 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.
Tue 4/216:23 pm
EYW
- PDX
2 stops24h 15m
Delta
Mon 4/2711:06 pm
PDX
- EYW
1 stop8h 40m
Delta
Deal found 3/18![Delta logo]()
$462
This Delta deal was found by Cheapflights users on 3/18. 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.
Wed 4/222:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Sun 4/266:28 am
PDX
- EYW
1 stop10h 12m
Delta
Deal found 3/18![Delta logo]()
$389
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 4/232:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Sat 5/210:55 pm
PDX
- EYW
1 stop8h 15m
Delta
Deal found 3/18![Delta logo]()
$414
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 4/232:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Sun 4/267:32 pm
PDX
- EYW
2 stops12h 14m
Delta
Deal found 3/18![Delta logo]()
$419
This Delta deal was found by Cheapflights users on 3/18. 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.
Thu 4/232:40 pm
EYW
- PDX
1 stop10h 22m
Delta
Mon 4/2711:06 pm
PDX
- EYW
1 stop8h 40m
Delta
Deal found 3/18![Delta logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 3/20. 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 4/309:58 am
EYW
- PDX
2 stops52h 44m
Multiple Airlines
Thu 5/282:44 pm
PDX
- EYW
1 stop17h 18m
Multiple Airlines
Deal found 3/20![Multiple Airlines logo]()
$357
One-way flights from Key West to PortlandSearch for one-way flight options from Key West to Portland. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
Search for one-way flight options from Key West to Portland. Find affordable one-way fares based on user searches. Data last updated March 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/234:22 pm
EYW
- PDX
3 stops46h 20m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$163
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:38 pm
EYW
- PDX
1 stop9h 20m
United Airlines
Deal found 3/17![United Airlines logo]()
$383
This United Airlines deal was found by Cheapflights users on 3/19. 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 8/54:00 pm
EYW
- PDX
1 stop9h 30m
United Airlines
Deal found 3/19![United Airlines logo]()
$758
This Delta deal was found by Cheapflights users on 3/19. 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 8/52:35 pm
EYW
- PDX
2 stops12h 18m
Delta
Deal found 3/19![Delta logo]()
$778
Find flight deals from Key West to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Portland (PDX). 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 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $357 (Kiwi.com) |
One-way from | $163 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to Portland 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 22, 2026.
Use the filters below to find and compare flights from Key West to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestPortland
EYW - PDX
EYWPDX
Key West
Thu 4/30
9:58 am-11:42 am
2 stops52h 44m
Portland
Thu 5/28
2:44 pm-11:02 am
1 stop17h 18m
$357
Key WestPortland
EYW - PDX
EYWPDX
Key West
Wed 4/22
2:40 pm-10:02 pm
1 stop10h 22m
Portland
Sun 4/26
6:05 pm-10:46 am
2 stops13h 41m
$394
Key WestPortland
EYW - PDX
EYWPDX
Key West
Thu 5/14
11:48 am-10:02 pm
2 stops13h 14m
Portland
Sat 5/23
5:18 pm-10:53 am
2 stops14h 35m
$399
Key WestPortland
EYW - PDX
EYWPDX
Key West
Thu 5/14
2:29 pm-9:38 pm
1 stop10h 09m
Portland
Sat 5/23
10:59 pm-1:05 pm
2 stops11h 06m
$414
Quickest round-trip
Key WestPortland
EYW - PDX
EYWPDX
Key West
Fri 4/3
3:56 pm-12:22 am
1 stop11h 26m
Portland
Sun 4/5
5:40 am-4:24 pm
1 stop7h 44m
$449
Cheapest one-way
Key WestPortland
EYW - PDX
EYWPDX
Key West
Thu 4/23
4:22 pm-11:42 am
3 stops46h 20m
$163
Quickest one-way
Key WestPortland
EYW - PDX
EYWPDX
Key West
Thu 4/23
4:38 pm-10:58 pm
1 stop9h 20m
$383
Key WestPortland
EYW - PDX
EYWPDX
Key West
Wed 8/5
4:00 pm-10:30 pm
1 stop9h 30m
$758
Key WestPortland
EYW - PDX
EYWPDX
Key West
Wed 8/5
2:35 pm-11:53 pm
2 stops12h 18m
$778
Sorted by cheapest first
- Most accurate provider: When it comes to deals on Key West-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Portland 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 Key West-Portland 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 Key West to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Key West with our price prediction graph.
EYW-PDX
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.
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated March 22, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Portland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.5
Crew
7.9
Entertainment
6.9
Comfort
7.2
Overall
7.1
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
Boarding
7.5
Crew
7.9
Entertainment
6.9
Comfort
7.2
Overall
7.1
Food
6.4
Reviews
1 / 20
2.0
MediocreAnonymous,Mar 2026
MIA - SFO
Related info for your journey
Find useful and relevant information for your journey from Key West to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsVancouver
Seaside
Clackamas
Lincoln City
Longview
Lake Oswego
Hillsboro
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Beaverton
Depoe Bay
Wilsonville
Stevenson
Tillamook
Pacific City
Astoria
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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Key West and Portland flights
Browse other Key West and Portland flight options. Last updated on March 22, 2026.
Other flights from Key West
Browse through other flights departing from Key West. Flights are based on user searches made on Cheapflights and were last updated on March 22, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on March 22, 2026.
Top airline flying from Key West to Portland
Discover the top airline that operate flights from Key West to Portland. 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 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$344 | Average$574 | FlexibilityNo cancel fee | On-time71% |