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Key West

$309+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — EYW
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$309
(American Airlines)

Popular in

August

Cheapest in

September

Average price

$581
From Oregon to Key West
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/29. 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.
Fri 9/129:56 pmPDX - EYW
1 stop10h 17mAmerican Airlines
Fri 9/1912:09 pmEYW - PDX
1 stop11h 28mAmerican Airlines
Deal found 7/29$309
This Delta deal was found by Cheapflights users on 7/30. 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.
Sat 8/236:14 amPDX - EYW
2 stops10h 58mDelta
Sat 8/307:00 amEYW - PDX
1 stop8h 41mDelta
Deal found 7/30$339
This United Airlines deal was found by Cheapflights users on 7/29. 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 12/211:19 pmPDX - EYW
1 stop11h 47mUnited Airlines
Sat 12/63:53 pmEYW - PDX
1 stop9h 22mUnited Airlines
Deal found 7/29$370
This Delta deal was found by Cheapflights users on 7/28. 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 8/235:30 amBOI - EYW
2 stops9h 42mDelta
Wed 8/277:00 amEYW - BOI
1 stop7h 35mDelta
Deal found 7/28$442
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/235:15 pmBOI - EYW
2 stops15h 38mAmerican Airlines
Wed 8/271:13 pmEYW - BOI
2 stops10h 30mAmerican Airlines
Deal found 7/29$492
This Mytrip deal was found by Cheapflights users on 7/29. 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 9/1812:07 pmPDX - EYW
2 stops23h 29mMultiple Airlines
Mon 9/2212:32 pmEYW - PDX
2 stops25h 40mMultiple Airlines
Deal found 7/29$528
This Mytrip deal was found by Cheapflights users on 7/28. 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 8/216:06 pmBOI - EYW
2 stops20h 45mMultiple Airlines
Sun 8/2410:02 amEYW - BOI
3 stops33h 09mMultiple Airlines
Deal found 7/28$665
This United Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 8/2312:27 pmBOI - EYW
2 stops23h 34mUnited Airlines
Wed 8/273:41 pmEYW - BOI
3 stops24h 08mUnited Airlines
Deal found 7/30$941

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 July 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

Fri 9/12

9:56 pm-11:13 am

1 stop10h 17m

Key West

Fri 9/19

12:09 pm-8:37 pm

1 stop11h 28m

$309

PortlandKey West

PDX - EYW

PDXEYW

Portland

Sat 8/23

6:14 am-8:12 pm

2 stops10h 58m

Key West

Sat 8/30

7:00 am-12:41 pm

1 stop8h 41m

$339

PortlandKey West

PDX - EYW

PDXEYW

Portland

Tue 12/2

11:19 pm-2:06 pm

1 stop11h 47m

Key West

Sat 12/6

3:53 pm-10:15 pm

1 stop9h 22m

$370

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 8/23

5:30 am-5:12 pm

2 stops9h 42m

Key West

Wed 8/27

7:00 am-12:35 pm

1 stop7h 35m

$442

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 8/23

5:15 pm-10:53 am

2 stops15h 38m

Key West

Wed 8/27

1:13 pm-9:43 pm

2 stops10h 30m

$492

PortlandKey West

PDX - EYW

PDXEYW

Portland

Thu 9/18

12:07 pm-2:36 pm

2 stops23h 29m

Key West

Mon 9/22

12:32 pm-11:12 am

2 stops25h 40m

$528

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Thu 8/21

6:06 pm-4:51 pm

2 stops20h 45m

Key West

Sun 8/24

10:02 am-5:11 pm

3 stops33h 09m

$665

BoiseKey West

BOI - EYW

BOIEYW

Boise Air Term. Gowen Fld

Sat 8/23

12:27 pm-2:01 pm

2 stops23h 34m

Key West

Wed 8/27

3:41 pm-1:49 pm

3 stops24h 08m

$941

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 July 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.

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 July 31, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Oregon to Key West by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,902 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Comfort

7.9

Food

7.3

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$261Average$428FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$271Average$577FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$317Average$688FlexibilityNo cancel feeOn-time69%

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