$202+ Cheap flights from Key West to Portland (EYW - PDX)
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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Nov 7 — Nov 141
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
Cheapest
Best
Last-minute
One-way
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 October 8, 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 October 8, 2026.
This American Airlines deal was found by Cheapflights users on 10/7. 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 12/26:35 pm -
1 stop8h 38m
Sat 12/511:10 pm -
1 stop7h 34m
Deal found 10/7![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 10/8. 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 10/232:34 pm -
1 stop9h 37m
Tue 10/276:30 am -
1 stop7h 24m
Deal found 10/8![American Airlines logo]()
$479
This American Airlines deal was found by Cheapflights users on 10/7. 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 12/14:43 pm -
1 stop10h 29m
Sat 12/511:13 pm -
1 stop9h 54m
Deal found 10/7![American Airlines logo]()
$518
This Delta deal was found by Cheapflights users on 10/7. 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 12/27:25 am -
2 stops14h 33m
Sat 12/55:59 pm -
2 stops13h 49m
Deal found 10/7![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/232:15 pm -
1 stop10h 12m
Tue 10/277:10 am -
2 stops27h 44m
Deal found 10/6![United Airlines logo]()
$773
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 October 8, 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 October 8, 2026.
This American Airlines deal was found by Cheapflights users on 10/7. 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 12/210:14 am -
2 stops14h 47m
Sat 12/511:13 pm -
1 stop9h 54m
Deal found 10/7![American Airlines logo]()
$551
This Delta deal was found by Cheapflights users on 10/7. 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 12/27:25 am -
2 stops14h 33m
Sat 12/55:59 pm -
2 stops13h 49m
Deal found 10/7![Delta logo]()
$625
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/232:15 pm -
1 stop10h 12m
Tue 10/277:10 am -
2 stops27h 44m
Deal found 10/6![United Airlines logo]()
$773
Last-minute flights from Key West to PortlandDiscover last-minute flight deals from Key West to Portland. Data last updated October 8, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Portland. Data last updated October 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 10/8. 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 10/232:34 pm -
1 stop9h 37m
Tue 10/276:30 am -
1 stop7h 24m
Deal found 10/8![American Airlines logo]()
$479
This United Airlines deal was found by Cheapflights users on 10/6. 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.
Fri 10/232:15 pm -
1 stop10h 12m
Tue 10/277:10 am -
2 stops27h 44m
Deal found 10/6![United Airlines logo]()
$773
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 October 8, 2026.
Search for one-way flight options from Key West to Portland. Find affordable one-way fares based on user searches. Data last updated October 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/101:16 pm -
3 stops49h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 10/7. 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 1/2410:59 am -
3 stops55h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Multiple Airlines logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 11/83:03 pm -
3 stops47h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/5. 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 3/312:19 pm -
3 stops29h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$288
This American Airlines deal was found by Cheapflights users on 10/5. 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 3/31:00 pm -
1 stop10h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![American Airlines logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 10/6. 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 1/3012:19 pm -
3 stops29h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$307
This American Airlines deal was found by Cheapflights users on 10/8. 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 11/106:35 pm -
1 stop20h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![American Airlines logo]()
$348
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 October 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $399 (American Airlines) |
One-way from | $225 (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 October 8, 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
Sun 1/24
10:59 am-3:03 pm
3 stops55h 04m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$225
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Tue 11/10
1:16 pm-11:07 am
2 stops48h 51m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$235
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 3/3
12:19 pm-3:03 pm
3 stops29h 44m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$288
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 3/3
1:00 pm-8:45 pm
1 stop10h 45m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$303
Quickest round-trip
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Sat 1/30
1:53 pm-8:06 pm
1 stop9h 13m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$350
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Mon 11/2
1:14 pm-7:47 pm
1 stop9h 33m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$363
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Sat 1/30
12:19 pm-3:03 pm
2 stops29h 44m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$377
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Mon 11/2
4:10 pm-10:27 pm
1 stop9h 17m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$428
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 12/2
10:14 am-10:01 pm
2 stops14h 47m
Portland
Sat 12/5
11:13 pm-12:07 pm
1 stop9h 54m
$551
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Wed 12/2
7:25 am-6:58 pm
2 stops14h 33m
Portland
Sat 12/5
5:59 pm-10:48 am
2 stops13h 49m
$625
Showing 1-10 of 11 resultsSorted by cheapest first
Compare providers for flights from Key West to Portland
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 Key West to Portland in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- 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
Durham
Longview
Lake Oswego
Cannon Beach
Vancouver
Kelso
Troutdale
Lincoln City
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Tillamook
Hillsboro
Astoria
Gresham
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