EYW - PDX

$168 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 4/13. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$329
American Airlines
Thu 5/14Sat 5/23
EYW - PDX • 1 stop
Cheapest one-way
$168
Multiple Airlines
Mon 4/13
EYW - PDX • 3 stops
Top airlines
American Airlines
Cheapest • from $329 (round-trip)
American Airlines
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Key West and Portland. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Dallas (DFW)
Cheapest • Avg $538 (round-trip)
Dallas (DFW)
Shortest trip • 9h 36m (one-way)
Insights
Insights
Insights
Insights
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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!
Flight Deals
Booking Insights
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, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:53 pm
EYW
-
PDX
10h 55m
1 stop
American Airlines Logo
10:30 pm - 1:41 pm
PDX
-
EYW
12h 11m
1 stop
$329American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:53 pm
EYW
-
PDX
10h 55m
1 stop
American Airlines Logo
10:59 pm - 1:41 pm
PDX
-
EYW
11h 42m
2 stops
$340American Airlines
Fri, Mar 6 - Tue, Mar 10
United Airlines Logo
2:24 pm - 9:52 pm
EYW
-
PDX
10h 28m
1 stop
United Airlines Logo
10:54 pm - 1:23 pm
PDX
-
EYW
11h 29m
1 stop
$389United Airlines
Fri, Mar 6 - Tue, Mar 10
Delta Logo
2:46 pm - 10:08 pm
EYW
-
PDX
10h 22m
1 stop
Delta Logo
7:43 pm - 10:48 am
PDX
-
EYW
12h 05m
2 stops
$394Delta
Fri, Mar 6 - Mon, Mar 9
American Airlines Logo
1:55 pm - 12:17 am
EYW
-
PDX
13h 22m
2 stops
American Airlines Logo
11:59 pm - 4:49 pm
PDX
-
EYW
13h 50m
2 stops
$405American Airlines
Sat, Apr 4 - Mon, Apr 13
American Airlines Logo
4:20 pm - 12:22 am
EYW
-
PDX
11h 02m
1 stop
American Airlines Logo
10:28 pm - 10:54 am
PDX
-
EYW
9h 26m
1 stop
$417American Airlines
Sat, Apr 4 - Sun, Apr 12
American Airlines Logo
4:20 pm - 12:22 am
EYW
-
PDX
11h 02m
1 stop
American Airlines Logo
12:59 am - 4:30 pm
PDX
-
EYW
12h 31m
2 stops
$422American Airlines
Thu, Mar 5 - Tue, Mar 10
United Airlines Logo
4:05 pm - 10:45 pm
EYW
-
PDX
9h 40m
1 stop
United Airlines Logo
10:54 pm - 1:23 pm
PDX
-
EYW
11h 29m
1 stop
$439United Airlines
Thu, Mar 5 - Tue, Mar 10
Delta Logo
11:59 am - 10:24 pm
EYW
-
PDX
13h 25m
2 stops
Delta Logo
10:30 pm - 10:48 am
PDX
-
EYW
9h 18m
1 stop
$444Delta
Thu, Mar 5 - Tue, Mar 10
Delta Logo
7:10 am - 4:10 pm
EYW
-
PDX
12h 00m
2 stops
Delta Logo
6:05 am - 7:41 pm
PDX
-
EYW
10h 36m
2 stops
$449Delta
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.

Which airlines provide the cheapest flights from Key West to Portland?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Portland were found on American Airlines ($329) and United Airlines ($389).

Find deals

Good to know

Cheapest flight$168
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 $168 for a one-way ticket and $329 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 11339 reviews
6.4Food
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
Airline reviews

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

8.0 ExcellentTeresa, Feb 2026
MIA - DCA
Read more American Airlines reviews

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

The smell from the bathroom kept wafting through the cabin. It made people sick.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

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

Information on your arrival and departure airports

Key West (EYW)
Portland (PDX)