$327 Find Cheap Flights from Key West to Oregon

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Oregon departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Oregon

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Oregon, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Oregon, as well as popular online travel agencies
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Cheap Flights from Key West to Oregon

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Portland
Portland1 stop$486
Portland
Portland1 stop$486

Book Cheap Key West to Oregon Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Oregon that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Oregon

Fri, Nov 21 - Fri, Nov 28
American Airlines Logo
2:39 pm - 10:59 pmEYW-PDX
11h 20m1 stop
American Airlines Logo
10:15 pm - 12:13 pmPDX-EYW
10h 58m1 stop
$486American Airlines
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Fri, Nov 21 - Fri, Nov 28
American Airlines Logo
2:39 pm - 10:59 pmEYW-PDX
11h 20m1 stop
American Airlines Logo
7:40 am - 11:50 pmPDX-EYW
13h 10m2 stops
$491American Airlines
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:00 pm - 11:05 amEYW-PDX
20h 05m1 stop
Delta Logo
5:10 pm - 11:03 amPDX-EYW
14h 53m2 stops
$492Delta
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:00 pm - 11:05 amEYW-PDX
20h 05m1 stop
Delta Logo
5:10 pm - 11:03 amPDX-EYW
14h 53m2 stops
$523Delta
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:00 pm - 7:18 pmEYW-PDX
28h 18m1 stop
Delta Logo
6:04 am - 5:12 pmPDX-EYW
8h 08m1 stop
$525Delta
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Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:00 pm - 7:18 pmEYW-PDX
28h 18m1 stop
Delta Logo
5:10 pm - 11:03 amPDX-EYW
14h 53m2 stops
$530Delta
Find Deal
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
1:42 pm - 8:24 pmEYW-PDX
9h 42m1 stop
American Airlines Logo
10:59 pm - 10:59 amPDX-EYW
9h 00m1 stop
$538American Airlines
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Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
3:57 pm - 10:57 pmEYW-PDX
10h 00m2 stops
American Airlines Logo
6:42 pm - 10:59 amPDX-EYW
13h 17m2 stops
$578American Airlines
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Fri, Nov 21 - Fri, Nov 28
Delta Logo
7:40 am - 5:43 pmEYW-PDX
13h 03m2 stops
Delta Logo
11:15 pm - 2:03 pmPDX-EYW
11h 48m2 stops
$587Delta
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Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
12:10 pm - 8:24 pmEYW-PDX
11h 14m2 stops
American Airlines Logo
6:42 pm - 10:59 amPDX-EYW
13h 17m2 stops
$596American Airlines
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Booking Insights

KAYAK's insights & trends for Key West to Oregon flights

Get data-powered insights and trends into flights from Key West to Oregon to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Key West to Oregon?

The average price of all round-trip flights from Key West to Oregon clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Oregon on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Key West to Oregon. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

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Good to know

Cheapest flight$327
Flight from Key West to Portland

FAQs - booking Oregon flights

  • How does KAYAK find such low prices on flights from Key West to Oregon?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Oregon.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Oregon?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Oregon is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Oregon?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Key West to Oregon with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Oregon?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Key West to Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Oregon?

    The cheapest time of day to fly to Oregon is generally in the afternoon, when round-trip flights cost $358 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Oregon is generally in the morning, which is peak travel time and where the average cost of a ticket is $498.

Reviews of the top airline flying from Key West to Oregon

 
See real verified KAYAK customer reviews for airlines flying from Key West to Oregon. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West to Oregon? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
American AirlinesOverall score based on 10000 reviews
6.9Entertainment
6.4Food
7.2Comfort
7.5Boarding
8.0Crew
Airline reviews

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

2.0 MediocreSydney, Sep 2025MIA - LAS
Read more American Airlines reviews

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Everything you need to know for your flight from Key West to Oregon

Information on your arrival and departure airports

Key West (EYW)

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