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Key West

$215+ Cheap flights from Oregon to Key West (EYW)

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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Oregon to Key West

Keep the following information in mind while searching for Oregon to Key West flight deals. Data was last updated May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$309
(American Airlines)

One-way from

$215
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$479
Provider with most accurate pricing for Portland-Key West flight deals.
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Provider most trusted by Cheapflights users for Portland-Key West flights.
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From Oregon to Key West
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One-way flight from Oregon to Key West
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Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Oregon to Key West

Cheapest flights from Oregon to Key West
Explore the most affordable flight options available from Oregon to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 12/36:04 amPDX - EYW
1 stop9h 26mAmerican Airlines
Wed 12/108:10 amEYW - PDX
1 stop11h 56mAmerican Airlines
Deal found 4/30$309
This Delta deal was found by Cheapflights users on 4/30. 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 12/36:00 amPDX - EYW
2 stops10h 44mDelta
Wed 12/107:00 amEYW - PDX
2 stops12h 12mDelta
Deal found 4/30$319
This United Airlines deal was found by Cheapflights users on 4/30. 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.
Tue 5/2710:55 pmPDX - EYW
1 stop10h 58mUnited Airlines
Tue 6/32:12 pmEYW - PDX
1 stop10h 37mUnited Airlines
Deal found 4/30$439
This American Airlines deal was found by Cheapflights users on 4/30. 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.
Sun 5/47:05 amBOI - EYW
1 stop7h 11mAmerican Airlines
Wed 5/1411:28 amEYW - BOI
2 stops12h 32mAmerican Airlines
Deal found 4/30$459
This United Airlines deal was found by Cheapflights users on 4/30. 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 5/307:07 pmBOI - EYW
2 stops16h 09mUnited Airlines
Fri 6/68:45 amEYW - BOI
2 stops30h 47mUnited Airlines
Deal found 4/30$463
This Delta deal was found by Cheapflights users on 4/30. 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 5/3011:59 pmBOI - EYW
1 stop8h 52mDelta
Fri 6/67:00 amEYW - BOI
1 stop7h 08mDelta
Deal found 4/30$679
This Mytrip deal was found by Cheapflights users on 4/30. 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 5/155:40 pmPDX - EYW
3 stops20h 01mMultiple Airlines
Mon 5/1910:23 amEYW - PDX
3 stops33h 22mMultiple Airlines
Deal found 4/30$795

Cheapflights Fare Finder

Customize your flight search to find flights from Oregon to Key West 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 May 1, 2025.
Use the filters below to find and compare flights from Oregon to Key West that are best for you.

Fly from

Oregon

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sun 7/13

11:07 pm-1:51 pm

1 stop11h 44m

Key West

Fri 8/22

2:31 pm-9:17 pm

1 stop9h 46m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 8/4

4:55 pm-10:51 am

2 stops14h 56m

Key West

Thu 8/14

7:00 am-7:16 pm

2 stops15h 16m

$319

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 8/7

6:43 pm-12:15 pm

2 stops14h 32m

Key West

Mon 8/11

6:45 pm-5:31 pm

2 stops25h 46m

$374

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 5/30

7:07 pm-1:16 pm

2 stops16h 09m

Key West

Fri 6/6

8:45 am-1:32 pm

2 stops30h 47m

$463

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 5/30

7:14 am-4:40 pm

1 stop7h 26m

Key West

Fri 6/6

1:24 pm-11:19 pm

2 stops11h 55m

$588

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Fri 5/30

11:59 pm-10:51 am

1 stop8h 52m

Key West

Fri 6/6

7:00 am-12:08 pm

1 stop7h 08m

$679

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 7/29

11:59 pm-8:00 am

2 stops29h 01m

$215

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 7/28

12:59 am-4:18 pm

2 stops12h 19m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Best time to book a flight from Oregon to Key West

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

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

Currently, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon to Key West in March is currently the most expensive (average of $492). 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.

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

Find hourly flight availability from Oregon to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 1, 2025.

When flying from Oregon to Key West, 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 Key West by month

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

In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.

Temperature in Key West by month

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

If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 F).

Reviews of airlines servicing Key West

Get insights into the airlines that provide service to Key West. 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 Key West. Reviews last updated May 1, 2025.
To help decide which airline to fly from Oregon to Key West, see what other customers have to say about Delta, United Airlines and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Delta
8.0
Very good
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,934 reviews

Overall

8.0

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Crew

8.5

Food

7.3

Reviews

1 / 20
2.0
Mediocre

Joseph,Aug 2023

MSP - MCO

Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.

Related info for your journey

Find useful and relevant information for your journey from Oregon to Key West. 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 into for flights to Key West from Oregon?

    Located just 2.6 mi from the city center, Key West (EYW) is the airport most travelers will use when flying to Key West from Oregon.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oregon to Key West 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 Oregon to Key West?

    Currently, August is the cheapest month in which you can book a flight from Oregon to Key West (average of $328). Flying from Oregon to Key West in March is currently the most expensive (average of $492). 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 3 airlines flying from Oregon to Key West

Discover the top 3 airlines that operate flights from Oregon to Key West. 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$278Average$564FlexibilityNo cancel feeOn-time71%
DeltaCheapest$284Average$412FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$558Average$672FlexibilityNo cancel feeOn-time69%

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