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$187+ 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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — PDX
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
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Cheap 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 February 4, 2026.

This American Airlines deal was found by Cheapflights users on 2/4. 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.
Thu 5/143:58 pm
EYW
-
PDX
1 stop10h 55m
American Airlines
Sat 5/2311:30 pm
PDX
-
EYW
2 stops13h 42m
American Airlines
Deal found 2/4$334
This American Airlines deal was found by Cheapflights users on 2/2. 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 2/171:55 pm
EYW
-
PDX
2 stops13h 22m
American Airlines
Sat 2/219:44 pm
PDX
-
EYW
1 stop10h 27m
American Airlines
Deal found 2/2$394
This Delta deal was found by Cheapflights users on 2/2. 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 5/147:30 am
EYW
-
PDX
2 stops14h 53m
Delta
Sat 5/235:51 pm
PDX
-
EYW
2 stops14h 02m
Delta
Deal found 2/2$429
This American Airlines deal was found by Cheapflights users on 2/4. 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 4/44:20 pm
EYW
-
PDX
1 stop11h 02m
American Airlines
Mon 4/1310:28 pm
PDX
-
EYW
1 stop9h 26m
American Airlines
Deal found 2/4$476

Find 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 February 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$334
(American Airlines)

One-way from

$187
(Kiwi.com)
Provider with most accurate pricing for Key West-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Key West-Portland flights.
Search Deals
From Key West to Oregon
Search Deals
One-way flight from Key West to Oregon
Search Deals

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 February 4, 2026.
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

Thu 5/14

3:58 pm-11:53 pm

1 stop10h 55m

Portland

Sat 5/23

11:30 pm-4:12 pm

2 stops13h 42m

$334

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 2/17

1:55 pm-12:17 am

2 stops13h 22m

Portland

Sat 2/21

9:44 pm-11:11 am

1 stop10h 27m

$394

Key WestPortland

EYW - PDX

EYWPDX

Key West

Thu 5/14

7:30 am-7:23 pm

2 stops14h 53m

Portland

Sat 5/23

5:51 pm-10:53 am

2 stops14h 02m

$429

Key WestPortland

EYW - PDX

EYWPDX

Key West

Sat 4/4

4:20 pm-12:22 am

1 stop11h 02m

Portland

Mon 4/13

6:22 am-6:16 pm

1 stop8h 54m

$476

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 3/4

12:40 pm-11:09 am

3 stops49h 29m

$187

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 4/28

1:01 pm-8:59 am

3 stops46h 58m

$237

Key WestPortland

EYW - PDX

EYWPDX

Key West

Wed 3/4

2:45 pm-9:52 pm

1 stop10h 07m

$353

Key WestPortland

EYW - PDX

EYWPDX

Key West

Tue 4/28

2:35 pm-9:59 pm

1 stop10h 24m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

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
No data available for this route at this time. Please check back soon.

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 February 4, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Oregon. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.
American Airlines
7.2
Good
11,216 reviews
American Airlines
7.2
Good
11,216 reviews

Boarding

7.5

Entertainment

6.9

Crew

8.0

Overall

7.2

Food

6.4

Comfort

7.2

Reviews

1 / 20
4.0
Okay

Susie,Jan 2026

TPA - CLT

I was sitting at the back of the plane and the flight attendants were so loud, talking to each other and laughing! I thought they were having a party back there.

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.

  • How long is the flight from Key West to Oregon?

    For as low as $334, American Airlines can have you in Oregon from Key West in 10h 55m. The distance between Key West and Oregon is about 2685 mi.

  • 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.

See more FAQs

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Top airline flying from Key West to Oregon

Discover the top airline 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$344Average$574FlexibilityNo cancel feeOn-time71%

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