$211+ 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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Portland 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 Key West to Portland
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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 August 19, 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 August 19, 2026.
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:40 am -
1 stop8h 18m
Wed 9/166:45 am -
1 stop10h 15m
Deal found 8/15![Delta logo]()
$473
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:20 pm -
1 stop10h 43m
Sat 9/1211:09 pm -
1 stop11h 20m
Deal found 8/16![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:40 am -
1 stop8h 58m
Thu 10/296:50 am -
1 stop10h 11m
Deal found 8/16![Delta logo]()
$509
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:56 pm -
1 stop10h 03m
Sun 9/611:30 pm -
1 stop10h 25m
Deal found 8/18![American Airlines logo]()
$519
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.
Wed 10/2112:48 pm -
1 stop10h 06m
Thu 10/295:20 am -
1 stop8h 34m
Deal found 8/17![American Airlines logo]()
$560
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:20 pm -
1 stop10h 43m
Tue 9/2211:09 pm -
1 stop11h 20m
Deal found 8/18![United Airlines logo]()
$579
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.
Wed 9/24:56 pm -
1 stop10h 03m
Wed 9/1611:08 pm -
2 stops11h 03m
Deal found 8/17![American Airlines logo]()
$601
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 August 19, 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 August 19, 2026.
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:20 pm -
1 stop10h 43m
Sat 9/1211:09 pm -
1 stop11h 20m
Deal found 8/17![United Airlines logo]()
$489
This Delta deal was found by Cheapflights users on 8/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:40 am -
1 stop8h 58m
Thu 10/296:50 am -
1 stop10h 11m
Deal found 8/16![Delta logo]()
$509
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/21:50 pm -
2 stops13h 09m
Sun 9/611:30 pm -
1 stop10h 25m
Deal found 8/18![American Airlines logo]()
$601
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.
Wed 9/24:56 pm -
1 stop10h 03m
Wed 9/1611:08 pm -
2 stops11h 03m
Deal found 8/17![American Airlines logo]()
$601
This United Airlines deal was found by Cheapflights users on 8/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/202:15 pm -
1 stop10h 12m
Sat 10/2410:33 pm -
1 stop12h 19m
Deal found 8/15![United Airlines logo]()
$677
Last-minute flights from Key West to PortlandDiscover last-minute flight deals from Key West to Portland. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Portland. Data last updated August 19, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:40 am -
1 stop8h 18m
Wed 9/166:45 am -
1 stop10h 15m
Deal found 8/15![Delta logo]()
$473
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:56 pm -
1 stop10h 03m
Sun 9/611:30 pm -
1 stop10h 25m
Deal found 8/18![American Airlines logo]()
$519
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.
Wed 9/24:56 pm -
1 stop10h 03m
Wed 9/1611:08 pm -
2 stops11h 03m
Deal found 8/17![American Airlines logo]()
$601
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/102:20 pm -
1 stop10h 43m
Sat 9/1211:09 pm -
1 stop11h 20m
Deal found 8/16![United Airlines logo]()
$489
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:20 pm -
1 stop10h 43m
Tue 9/2211:09 pm -
1 stop11h 20m
Deal found 8/18![United Airlines logo]()
$579
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/152:34 pm -
1 stop11h 54m
Tue 9/2211:06 pm -
1 stop11h 05m
Deal found 8/18![American Airlines logo]()
$645
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 August 19, 2026.
Search for one-way flight options from Key West to Portland. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 9/1610:04 am -
3 stops52h 39m
Deal found 8/16![Multiple Airlines logo]()
$211
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/211:46 am -
3 stops28h 06m
Deal found 8/18![Multiple Airlines logo]()
$292
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/293:33 pm -
2 stops51h 07m
Deal found 8/17![Multiple Airlines logo]()
$411
This United Airlines deal was found by Cheapflights users on 8/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/162:20 pm -
1 stop10h 43m
Deal found 8/16![United Airlines logo]()
$420
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $473 (Delta) |
One-way from | $211 (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 7,457,451 searches. Data last updated August 19, 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 Key West - PDX Portland
EYWPDX
Key West
Thu 9/10
2:20 pm-10:03 pm
1 stop10h 43m
Portland
Sat 9/12
11:09 pm-1:29 pm
1 stop11h 20m
$489
Quickest round-trip
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 10/21
7:40 am-1:38 pm
1 stop8h 58m
Portland
Thu 10/29
6:50 am-8:01 pm
1 stop10h 11m
$509
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 9/2
1:50 pm-11:59 pm
2 stops13h 09m
Portland
Sun 9/6
11:30 pm-12:55 pm
1 stop10h 25m
$601
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 9/2
4:56 pm-11:59 pm
1 stop10h 03m
Portland
Wed 9/16
11:08 pm-1:11 pm
2 stops11h 03m
$601
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Tue 10/20
2:15 pm-9:27 pm
1 stop10h 12m
Portland
Sat 10/24
10:33 pm-1:52 pm
1 stop12h 19m
$677
Cheapest one-way
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 9/16
10:04 am-11:43 am
3 stops52h 39m
$211
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 9/2
11:46 am-12:52 pm
3 stops28h 06m
$296
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Sun 11/29
3:33 pm-3:40 pm
2 stops51h 07m
$411
Quickest one-way
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 9/16
2:20 pm-10:03 pm
1 stop10h 43m
$420
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.
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 locationsBeaverton
Seaside
Lincoln City
Durham
Longview
Lake Oswego
Kelso
Clackamas
Troutdale
Vancouver
Cannon Beach
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
Silverton
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