$393+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Nov 18 — Nov 251
1 adult, Economy
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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, 2025.
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, 2025.
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.
Fri 3/66:00 pmEYW - PDX
1 stop20h 05mDelta
Tue 3/109:45 pmPDX - EYW
1 stop10h 18mDelta
Deal found 10/16![Delta logo]()
$558
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.
Fri 3/63:48 pmEYW - PDX
1 stop9h 28mUnited Airlines
Tue 3/104:05 pmPDX - EYW
2 stops21h 03mUnited Airlines
Deal found 10/17![United Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 10/18. 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.
Fri 3/63:51 pmEYW - PDX
1 stop10h 06mAmerican Airlines
Tue 3/108:01 amPDX - EYW
2 stops12h 58mAmerican Airlines
Deal found 10/18![American Airlines logo]()
$573
Cheap 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, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $558 (Delta) |
One-way from | $393 (United Airlines) |
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 October 19, 2025.
Use the filters below to find and compare flights from Key West to Portland that are best for you.
Fly from
Key West
Fly to
Portland
Route
Depart
Return
Price
Key WestPortland
EYW - PDX
EYWPDX
Key West
Fri 3/6
6:00 pm-11:05 am
1 stop20h 05m
Portland
Tue 3/10
9:45 pm-11:03 am
1 stop10h 18m
$558
Key WestPortland
EYW - PDX
EYWPDX
Key West
Fri 3/6
3:48 pm-10:16 pm
1 stop9h 28m
Portland
Tue 3/10
4:05 pm-4:08 pm
2 stops21h 03m
$568
Key WestPortland
EYW - PDX
EYWPDX
Key West
Fri 3/6
3:51 pm-10:57 pm
1 stop10h 06m
Portland
Tue 3/10
8:01 am-11:59 pm
2 stops12h 58m
$573
Key WestPortland
EYW - PDX
EYWPDX
Key West
Wed 12/31
4:29 pm-10:01 am
2 stops20h 32m
$393
- 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.
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 Key West to Portland
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 October 19, 2025.
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
Food
6.4
Overall
7.2
Crew
8.0
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
MIA - DCA
Boarding
7.5
Food
6.4
Overall
7.2
Crew
8.0
Comfort
7.2
Entertainment
6.9
Reviews
1 / 20
2.0
MediocreAnonymous,Aug 2025
MIA - DCA
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
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The Dalles
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Alternative routes for Key West to Portland
See prices for flight routes from nearby airports that may be better suited for you.
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 October 19, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$344 | Average$574 | FlexibilityNo cancel fee | On-time71% |