$296+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Nov 18 — Nov 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
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 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 October 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 11/132:51 pm -
2 stops26h 46m
Tue 11/173:40 pm -
2 stops19h 12m
Deal found 10/16![United Airlines logo]()
$811
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 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 October 19, 2026.
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 11/132:51 pm -
2 stops26h 46m
Tue 11/173:40 pm -
2 stops19h 12m
Deal found 10/16![United Airlines logo]()
$811
Last-minute flights from Key West to PortlandDiscover last-minute flight deals from Key West to Portland. Data last updated October 19, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Portland. Data last updated October 19, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Fri 11/132:51 pm -
2 stops26h 46m
Tue 11/173:40 pm -
2 stops19h 12m
Deal found 10/16![United Airlines logo]()
$811
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 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 October 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 12/176:20 pm -
2 stops54h 01m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$296
This United Airlines deal was found by Cheapflights users on 10/17. 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 12/1712:22 pm -
1 stop9h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![United Airlines logo]()
$333
This American Airlines deal was found by Cheapflights users on 10/14. 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.
Mon 11/211:14 am -
1 stop15h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/14![American Airlines logo]()
$438
This Delta deal was found by Cheapflights users on 10/16. 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.
Mon 11/211:51 am -
1 stop10h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![Delta logo]()
$463
This United Airlines deal was found by Cheapflights users on 10/16. 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.
Mon 11/22:50 pm -
3 stops34h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/16![United Airlines logo]()
$670
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 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $811 (United Airlines) |
One-way from | $296 (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 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 12/17
6:20 pm-9:21 pm
2 stops54h 01m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$296
Quickest round-trip
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Thu 12/17
12:22 pm-6:53 pm
1 stop9h 31m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$333
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Mon 11/2
11:14 am-11:59 pm
1 stop15h 45m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$438
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Mon 11/2
11:51 am-7:09 pm
1 stop10h 18m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$463
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Mon 11/2
2:50 pm-10:27 pm
3 stops34h 37m
Portland
Wed 12/31
12:00 am-3:00 am
Nonstop0h 00m
$670
Key WestPortland
EYW Key West - PDX Portland
EYWPDX
Key West
Fri 11/13
2:51 pm-2:37 pm
2 stops26h 46m
Portland
Tue 11/17
3:40 pm-1:52 pm
2 stops19h 12m
$811
Sorted 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
Hillsboro
Tillamook
Astoria
Gresham
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