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$349+ Cheap flights from Key West (EYW) to Oregon

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 5/7. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Key West to Oregon

Keep the following information in mind while searching for Key West to Oregon flight deals. Data was last updated April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$349
(American Airlines)

Popular in

August

Cheapest in

September

Average price

$574
Provider with most accurate pricing for Key West-Portland flight deals.
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Provider most trusted by Cheapflights users for Key West-Portland flights.
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From Key West to Oregon
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High demand for flights, 0% potential price rise
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Cheapest flight prices on average. 6% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Key West to Oregon

Cheapest flights from Key West to Oregon
Explore the most affordable flight options available from Key West to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2025.

This American Airlines deal was found by Cheapflights users on 4/17. 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 5/73:17 pmEYW - PDX
2 stops11h 42mAmerican Airlines
Mon 5/1211:49 pmPDX - EYW
2 stops11h 48mAmerican Airlines
Deal found 4/17$349
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Wed 5/72:18 pmEYW - PDX
1 stop10h 21mUnited Airlines
Mon 5/1210:47 pmPDX - EYW
1 stop11h 16mUnited Airlines
Deal found 4/17$449

Cheapflights Fare Finder

Customize your flight search to find flights from Key West to Oregon 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 April 17, 2025.
Use the filters below to find and compare flights from Key West to Oregon that are best for you.

Fly from

Key West

Fly to

Oregon

Route

Depart

Return

Price

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 5/7

3:17 pm-11:59 pm

2 stops11h 42m

Portland

Mon 5/12

11:49 pm-2:37 pm

2 stops11h 48m

$349

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 5/7

2:18 pm-9:39 pm

1 stop10h 21m

Portland

Mon 5/12

10:47 pm-1:03 pm

1 stop11h 16m

$449

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Best time to book a flight from Key West to Oregon

Have a flexible travel schedule? Discover the best time to fly to Oregon 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 Oregon

What is the cheapest time of day to fly from EYW to OR?

Find hourly flight availability from Key West to Oregon. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2025.

When flying from Key West to Oregon, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Oregon by month

Plan your trip to Oregon by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Oregon ranges from 0.7 - 5.6 inches per month. November is typically the wettest month, when rainfall can reach 5.6 in. July is typically the driest time to visit Oregon when rainfall is around 0.7 in.

Temperature in Oregon by month

Plan your trip to Oregon by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Oregon, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 41.0 F).

Reviews of airlines servicing Oregon

Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated April 17, 2025.
United Airlines
7.4
Good
8,667 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,667 reviews
United Airlines
7.4
Good
8,667 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,667 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Comfort

7.3

Entertainment

7.0

Crew

8.1

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

Related info for your journey

Find useful and relevant information for your journey from Key West to Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Key West to Oregon?

    Key West (EYW) is the airport you will fly out of if you book a flight from Key West to Oregon. It is only a 2.6 mi journey to Key West (EYW) from Key West’s city center.

  • Can I find deals for flights from Key West to Oregon that include hotel bookings?

    Yes. In addition to deals on Key West to Oregon flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Key West to Oregon?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Key West to Oregon.

  • Can I find deals for business class flights from Key West to Oregon?

    Yes. Cheapflights offers flight deals from Key West to Oregon by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Key West to Oregon?

    Currently, November is the cheapest month in which you can book a flight from Key West to Oregon (average of $277). Flying from Key West to Oregon in March is currently the most expensive (average of $369). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 2 airlines flying from Key West to Oregon

Discover the top 2 airlines that operate flights from Key West to Oregon. 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$543FlexibilityNo cancel feeOn-time71%

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