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$130+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$249
(American Airlines)

One-way from

$130
(American Airlines)

Popular in

March

Cheapest in

August

Average price

$573
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. 15% potential increase in price ($97 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This American Airlines deal was found by Cheapflights users on 2/18. 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.
Tue 4/155:31 amPDX - EYW
1 stop7h 45mAmerican Airlines
Wed 4/233:56 pmEYW - PDX
1 stop10h 32mAmerican Airlines
Deal found 2/18$249
This Delta deal was found by Cheapflights users on 2/18. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1010:55 pmPDX - EYW
2 stops15h 18mDelta
Wed 5/147:00 amEYW - PDX
2 stops12h 09mDelta
Deal found 2/18$284
This United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1211:59 pmPDX - EYW
2 stops15h 56mUnited Airlines
Wed 4/164:04 pmEYW - PDX
1 stop9h 32mUnited Airlines
Deal found 2/18$425
This United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/610:00 amBOI - EYW
1 stop9h 03mUnited Airlines
Mon 3/1012:45 pmEYW - BOI
2 stops12h 30mUnited Airlines
Deal found 2/18$460
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sun 3/161:31 pmBOI - EYW
2 stops17h 31mMultiple Airlines
Sat 3/223:15 pmEYW - BOI
3 stops47h 21mMultiple Airlines
Deal found 2/19$587
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 7/87:33 amBOI - EYW
1 stop6h 43mAmerican Airlines
Tue 7/151:54 pmEYW - BOI
1 stop9h 09mAmerican Airlines
Deal found 2/19$599
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/71:30 pmBOI - EYW
3 stops22h 13mAlaska Airlines
Sat 7/1211:34 amEYW - BOI
2 stops14h 21mAlaska Airlines
Deal found 2/20$1,474

Find flights from Oregon to Key West within your budget

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 February 20, 2025.

Fly from

Oregon

Fly to

Key West

Route

Depart

Return

Price

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 4/15

5:31 am-4:16 pm

1 stop7h 45m

Key West

Wed 4/23

3:56 pm-11:28 pm

1 stop10h 32m

$249

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 5/10

10:55 pm-5:13 pm

2 stops15h 18m

Key West

Wed 5/14

7:00 am-4:09 pm

2 stops12h 09m

$284

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 3/6

11:38 pm-11:41 am

1 stop9h 03m

Key West

Tue 3/11

3:59 pm-10:56 pm

1 stop9h 57m

$409

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Thu 3/6

10:00 am-9:03 pm

1 stop9h 03m

Key West

Mon 3/10

12:45 pm-11:15 pm

2 stops12h 30m

$460

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sun 3/16

1:31 pm-9:02 am

2 stops17h 31m

Key West

Sat 3/22

3:15 pm-12:36 pm

3 stops47h 21m

$587

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Tue 7/8

7:33 am-4:16 pm

1 stop6h 43m

Key West

Tue 7/15

1:54 pm-9:03 pm

1 stop9h 09m

$599

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Mon 7/7

1:30 pm-1:43 pm

3 stops22h 13m

Key West

Sat 7/12

11:34 am-11:55 pm

2 stops14h 21m

$1,474

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 3/12

5:00 am-6:59 pm

2 stops10h 59m

$130

PortlandKey West

PDX - EYW

PDXEYW

Portland

Mon 3/31

7:30 pm-1:15 pm

2 stops14h 45m

$266

PortlandKey West

PDX - EYW

PDXEYW

Portland

Wed 3/12

6:30 am-5:20 pm

1 stop7h 50m

$270

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Oregon to Key West

Get recent, data-driven insights about flights from Oregon to Key West including ideal travel times, pricing trends, and more.

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 $510). 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 February 20, 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 February 20, 2025.
To help decide which airline to fly from Oregon to Key West, see what other customers have to say about Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Alaska Airlines
8.0
Very good
9,692 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Delta
8.0
Very good
8,220 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

United Airlines
7.4
Good
8,766 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
9,692 reviews

Entertainment

7.1

Boarding

8.2

Food

7.1

Comfort

7.9

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $130. Users have also found prices from $266 and $270 on United Airlines and Delta, respectively.

  • 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 $510). 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$288Average$630FlexibilityNo cancel feeOn-time71%
DeltaCheapest$307Average$413FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$431Average$605FlexibilityNo cancel feeOn-time69%
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