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Key West

$249+ Cheap flights from Oregon to Key West (EYW)

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 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
אפר' 5 — אפר' 121
ש' 4/5
ש' 4/12
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 מרץ 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$708
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
Search Deals
Highest demand for flights based on searches. 14% potential increase in price ($88 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 March 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 מרץ 31, 2025.

This American Airlines deal was found by Cheapflights users on 3/30. 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.
ג' 9/165:55 amPDX - EYW
1 stop7h 06mAmerican Airlines
ג' 9/231:35 pmEYW - PDX
1 stop10h 18mAmerican Airlines
Deal found 3/30$249
This Delta deal was found by Cheapflights users on 3/31. 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.
ג' 9/167:55 pmPDX - EYW
2 stops12h 04mDelta
ג' 9/237:00 amEYW - PDX
2 stops12h 12mDelta
Deal found 3/31$259
This Delta deal was found by Cheapflights users on 3/30. 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.
א' 4/206:15 amBOI - EYW
2 stops10h 06mDelta
ה' 4/243:00 pmEYW - BOI
1 stop9h 28mDelta
Deal found 3/30$399
This Mytrip deal was found by Cheapflights users on 3/30. 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.
ד' 5/211:37 pmPDX - EYW
3 stops24h 08mMultiple Airlines
א' 5/258:53 amEYW - PDX
2 stops32h 47mMultiple Airlines
Deal found 3/30$409
This American Airlines deal was found by Cheapflights users on 3/30. 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.
ג' 4/157:05 amBOI - EYW
1 stop7h 11mAmerican Airlines
ש' 4/193:06 pmEYW - BOI
2 stops10h 28mAmerican Airlines
Deal found 3/30$410
This United deal was found by Cheapflights users on 3/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ש' 5/1710:47 pmPDX - EYW
1 stop11h 12mUnited Airlines
ש' 5/248:45 amEYW - PDX
2 stops30h 48mUnited Airlines
Deal found 3/31$425
This United Airlines deal was found by Cheapflights users on 3/31. 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.
ו' 5/27:10 pmBOI - EYW
2 stops34h 50mUnited Airlines
ב' 5/58:45 amEYW - BOI
2 stops40h 07mUnited Airlines
Deal found 3/31$599

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 מרץ 31, 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

ג' 4/15

10:34 pm-10:53 am

1 stop9h 19m

Key West

ג' 4/22

3:56 pm-11:28 pm

1 stop10h 32m

$300

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

א' 4/20

6:15 am-6:21 pm

2 stops10h 06m

Key West

ה' 4/24

3:00 pm-10:28 pm

1 stop9h 28m

$399

PortlandKey West

PDX - EYW

PDXEYW

Portland

ד' 5/21

1:37 pm-4:45 pm

3 stops24h 08m

Key West

א' 5/25

8:53 am-2:40 pm

2 stops32h 47m

$409

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

ג' 4/15

7:05 am-4:16 pm

1 stop7h 11m

Key West

ש' 4/19

3:06 pm-11:34 pm

2 stops10h 28m

$410

PortlandKey West

PDX - EYW

PDXEYW

Portland

ש' 5/17

10:47 pm-12:59 pm

1 stop11h 12m

Key West

ש' 5/24

8:45 am-12:33 pm

2 stops30h 48m

$425

PortlandKey West

PDX - EYW

PDXEYW

Portland

ה' 4/3

12:59 am-5:15 pm

2 stops13h 16m

Key West

ד' 4/9

12:26 pm-6:02 pm

1 stop8h 36m

$540

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

ו' 5/2

7:10 pm-8:00 am

2 stops34h 50m

Key West

ב' 5/5

8:45 am-10:52 pm

2 stops40h 07m

$599

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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 $493). 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 מרץ 31, 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 מרץ 31, 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
7,899 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
7,899 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
8,614 reviews
Delta
8.0
Very good
7,899 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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
7,899 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Crew

8.5

Food

7.3

Overall

8.0

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 $493). 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 מרץ 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$285Average$573FlexibilityNo cancel feeOn-time71%
DeltaCheapest$289Average$412FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$317Average$621FlexibilityNo cancel feeOn-time69%
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