EYW - PDX

$194 Find Cheap Flights from Key West to Portland

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 Portland departing on 12/22. 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, 0 bags

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

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

Cheap Flights from Key West to Portland (EYW-PDX)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Portland 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 Portland

Thu, Nov 20 - Mon, Nov 24
American Airlines Logo
2:39 pm - 9:20 pmEYW-PDX
9h 41m1 stop
American Airlines Logo
5:30 am - 4:29 pmPDX-EYW
7h 59m1 stop
$389American Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
American Airlines Logo
2:39 pm - 9:20 pmEYW-PDX
9h 41m1 stop
American Airlines Logo
7:40 am - 11:50 pmPDX-EYW
13h 10m2 stops
$394American Airlines
Find Deal
Thu, Nov 20 - Mon, Nov 24
American Airlines Logo
11:44 am - 9:15 pmEYW-PDX
12h 31m2 stops
American Airlines Logo
7:40 am - 11:50 pmPDX-EYW
13h 10m2 stops
$399American Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
American Airlines Logo
2:25 pm - 9:48 pmEYW-PDX
10h 23m1 stop
American Airlines Logo
5:44 am - 4:17 pmPDX-EYW
7h 33m1 stop
$409American Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
American Airlines Logo
4:02 pm - 11:59 pmEYW-PDX
10h 57m1 stop
American Airlines Logo
11:59 pm - 3:56 pmPDX-EYW
12h 57m2 stops
$414American Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
American Airlines Logo
7:00 am - 6:09 pmEYW-PDX
14h 09m2 stops
American Airlines Logo
6:43 am - 10:59 pmPDX-EYW
13h 16m2 stops
$459American Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
2:22 pm - 9:54 pmEYW-PDX
10h 32m1 stop
United Airlines Logo
10:56 pm - 1:09 pmPDX-EYW
11h 13m1 stop
$492United Airlines
Find Deal
Thu, Nov 20 - Sun, Nov 23
American Airlines Logo
2:39 pm - 9:20 pmEYW-PDX
9h 41m1 stop
American Airlines Logo
12:59 am - 5:06 pmPDX-EYW
13h 07m2 stops
$511American Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
Delta Logo
6:07 pm - 7:03 pmEYW-PDX
27h 56m1 stop
Delta Logo
7:55 pm - 11:03 amPDX-EYW
12h 08m2 stops
$523Delta
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Fri, Mar 6 - Mon, Mar 9
Delta Logo
6:07 pm - 7:03 pmEYW-PDX
27h 56m1 stop
Delta Logo
12:55 am - 5:13 pmPDX-EYW
13h 18m2 stops
$582Delta
Find Deal

Everything you should know

Top airlines
American Airlines
Cheapest • from $389 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$389
American Airlines
Thu 11/20Mon 11/24
EYW - PDX • 1 stop
Cheapest one-way
$194
Typical prices: $335-$468
Multiple Airlines
Mon 12/22
EYW - PDX • 2 stops
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Booking Insights

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

Get data-powered insights and trends into flights from Key West to Portland 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 Portland?

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

If your flying dates are flexible, you should consider flying to Portland 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 Portland. For your return ticket, we recommend flying on a Monday and avoiding Fridays for the best deals.

Good to know

Cheapest flight$194
Flight from Key West to Portland

When to book flights from Key West to Portland

Are your dates flexible? Find out the best times to travel from Key West to Portland based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Key West to Portland

  • What is the cheapest flight from Key West to Portland?

    In the last 3 days, the lowest price for a flight from Key West to Portland was $194 for a one-way ticket and $389 for a round-trip.

  • Do I need a passport to fly between Key West and Portland?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which aircraft models fly most regularly from Key West to Portland?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Key West to Portland?

    oneworld is the only airline alliance operating flights between Key West and Portland.

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

    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 Portland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Key West 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 Portland?

    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 to Portland with an airline and back to Key West with another airline. Booking your flights between Key West and PDX can sometimes prove cheaper using this method.

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

    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 to Portland from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Key West to Portland

 
See real verified KAYAK customer reviews for airlines flying from Key West to Portland. 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 Portland? 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 11040 reviews
8.0Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

10.0 Excellentchloe, Nov 2025MCO - ORD
Read more American Airlines reviews

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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.

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

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