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$238+ Cheap flights from Key West (EYW) to Oregon

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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
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 July 29, 2025.

Round-trip from

$309
(American Airlines)

One-way from

$238
(Delta)

Popular in

August

Cheapest in

September

Average price

$488
From Key West to Oregon
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One-way flight from Key West to Oregon
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Highest demand for flights based on searches. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 8/301:58 pmEYW - PDX
1 stop9h 54mAmerican Airlines
Fri 9/59:56 pmPDX - EYW
1 stop10h 17mAmerican Airlines
Deal found 7/27$309
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 9/47:00 amEYW - PDX
2 stops11h 59mDelta
Thu 9/116:20 amPDX - EYW
2 stops10h 47mDelta
Deal found 7/27$344
This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/48:55 amEYW - PDX
3 stops29h 17mMultiple Airlines
Thu 9/1112:07 pmPDX - EYW
3 stops20h 45mMultiple Airlines
Deal found 7/27$591

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 July 29, 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

Sat 8/30

1:58 pm-8:52 pm

1 stop9h 54m

Portland

Fri 9/5

9:56 pm-11:13 am

1 stop10h 17m

$309

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 9/4

7:00 am-3:59 pm

2 stops11h 59m

Portland

Thu 9/11

6:20 am-8:07 pm

2 stops10h 47m

$344

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 9/4

8:55 am-11:12 am

3 stops29h 17m

Portland

Thu 9/11

12:07 pm-11:52 am

3 stops20h 45m

$591

Key WestPortland

EYW - PDX

EYWPDX

Key West

Fri 10/3

2:00 pm-9:47 pm

1 stop10h 47m

$238

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 9/4

8:55 am-11:12 am

3 stops29h 17m

$269

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 9/4

12:09 pm-8:37 pm

1 stop11h 28m

$343

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sun 11/9

4:00 pm-10:35 pm

1 stop9h 35m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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 July 29, 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.

How much does it cost to fly round-trip from Key West to Oregon?

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 July 29, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Key West to Oregon. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
8.0
Very good
7,977 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
United Airlines
7.4
Good
8,899 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,977 reviews

Comfort

7.9

Entertainment

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

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.

  • What are the cheapest airlines to fly from Key West to Oregon one-way?

    The cheapest airlines for a one-way flight from Key West to Oregon are Delta ($238), American Airlines ($343), and United Airlines ($429).

  • 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 $368). 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$288Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$308Average$574FlexibilityNo cancel feeOn-time71%

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