EYW - PDX

$334 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 3/4. 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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Everything you should know

Cheapest round-trip
$334
American Airlines
Thu 5/14Sat 5/23
EYW - PDX • 1 stop
Cheapest one-way
$187
Multiple Airlines
Wed 3/4
EYW - PDX • 3 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!
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
11:30 pm - 4:12 pm
PDX
-
EYW
13h 42m
2 stops
$334American Airlines
Thu, Mar 5 - Sun, Mar 15
American Airlines Logo
1:55 pm - 12:17 am
EYW
-
PDX
13h 22m
2 stops
American Airlines Logo
11:59 pm - 3:57 pm
PDX
-
EYW
12h 58m
2 stops
$339American Airlines
Thu, Mar 5 - Sun, Mar 15
American Airlines Logo
2:06 pm - 8:44 pm
EYW
-
PDX
9h 38m
1 stop
American Airlines Logo
11:59 pm - 12:54 pm
PDX
-
EYW
9h 55m
1 stop
$359American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
6:45 am - 4:59 pm
EYW
-
PDX
13h 14m
2 stops
American Airlines Logo
11:30 pm - 4:12 pm
PDX
-
EYW
13h 42m
2 stops
$369American 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
10:30 pm - 1:42 pm
PDX
-
EYW
12h 12m
1 stop
$417American 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
6:00 am - 6:52 pm
PDX
-
EYW
9h 52m
1 stop
$448American 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
$476American 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
6:22 am - 10:36 pm
PDX
-
EYW
13h 14m
2 stops
$481American Airlines
Thu, Mar 5 - Sat, Mar 14
American Airlines Logo
1:55 pm - 12:17 am
EYW
-
PDX
13h 22m
2 stops
American Airlines Logo
11:59 pm - 1:45 pm
PDX
-
EYW
10h 46m
2 stops
$486American Airlines
Thu, Mar 5 - Sat, Mar 14
American Airlines Logo
3:51 pm - 11:50 pm
EYW
-
PDX
10h 59m
1 stop
American Airlines Logo
11:59 pm - 4:49 pm
PDX
-
EYW
13h 50m
2 stops
$508American Airlines
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 is the most popular layover airport when flying from Key West to Portland?

Percentage of 1-stop round-trip flights from Key West to Portland chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Miami (MIA) is the top choice – 69% of KAYAK users who clicked on 1-stop flights from Key West to Portland picked an itinerary connecting there.

What is the cheapest layover airport when flying from Key West to Portland?

Average round-trip price for 1-stop flights from Key West to Portland clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Dallas (DFW) offer the most affordable fares, with an average round-trip price of $538.

Which layover airport offers the shortest total travel time from Key West to Portland?

Shortest average total travel time for 1-stop one-way flights from Key West to Portland via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Dallas (DFW) for the shortest journey. The average one-way travel time for flights connecting there is 9h 36m.

Which layover airport has the quickest connection when flying from Key West to Portland?

Average layover duration at different layover airports for 1-stop one-way flights from Key West to Portland, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Dallas (DFW) often has the shortest layovers from Key West to Portland, with an average of 2h 08m.

Find deals

Good to know

Cheapest flight$187
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 $483 for a one-way ticket and $334 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 11246 reviews
7.5Boarding
7.2Comfort
6.4Food
6.9Entertainment
8.0Crew
Airline reviews

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.

2.0 MediocreSalim, Feb 2026
JAX - PHL
Read more American Airlines reviews

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

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

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)