EYW - PDX

$260 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 2/15. 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
$329
American Airlines
Thu 5/14Sat 5/23
EYW - PDX • 1 stop
Cheapest one-way
$260
Multiple Airlines
Sun 2/15
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!
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 - 11:52 pm
EYW
-
PDX
10h 54m1 stop
American Airlines Logo
10:30 pm - 1:42 pm
PDX
-
EYW
12h 12m1 stop
$329American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:52 pm
EYW
-
PDX
10h 54m1 stop
American Airlines Logo
11:30 pm - 4:12 pm
PDX
-
EYW
13h 42m2 stops
$334American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:52 pm
EYW
-
PDX
10h 54m1 stop
American Airlines Logo
11:30 pm - 1:42 pm
PDX
-
EYW
11h 12m2 stops
$335American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
6:45 am - 4:59 pm
EYW
-
PDX
13h 14m2 stops
American Airlines Logo
11:30 pm - 4:12 pm
PDX
-
EYW
13h 42m2 stops
$486American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
2:01 pm - 10:32 pm
EYW
-
PDX
11h 31m2 stops
American Airlines Logo
11:30 pm - 1:42 pm
PDX
-
EYW
11h 12m2 stops
$487American Airlines
Wed, Jan 14 - Sun, Jan 18
United Airlines Logo
2:25 pm - 9:49 pm
EYW
-
PDX
10h 24m1 stop
United Airlines Logo
11:05 pm - 1:03 pm
PDX
-
EYW
10h 58m1 stop
$539United Airlines
Wed, Jan 14 - Sun, Jan 18
United Airlines Logo
2:25 pm - 9:49 pm
EYW
-
PDX
10h 24m1 stop
United Airlines Logo
11:05 pm - 1:03 pm
PDX
-
EYW
10h 58m1 stop
$589United Airlines
Wed, Jan 14 - Sun, Jan 18
United Airlines Logo
2:25 pm - 9:49 pm
EYW
-
PDX
10h 24m1 stop
United Airlines Logo
11:05 pm - 1:03 pm
PDX
-
EYW
10h 58m1 stop
$629United Airlines
Wed, Jan 14 - Sun, Jan 18
United Airlines Logo
2:25 pm - 9:49 pm
EYW
-
PDX
10h 24m1 stop
United Airlines Logo
5:00 am - 3:17 pm
PDX
-
EYW
31h 17m2 stops
$652United Airlines
Thu, May 14 - Sat, May 23
United Airlines Logo
3:52 pm - 12:48 am
EYW
-
PDX
35h 56m2 stops
United Airlines Logo
3:30 pm - 10:11 pm
PDX
-
EYW
27h 41m3 stops
$656United 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.

Which airlines fly non-stop between Key West and Portland?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for round-trip flights from Key West to Portland.

There is just one airline that flies from Key West to Portland direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is $344.

Find deals

Good to know

Cheapest flight$260
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 $260 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 11081 reviews
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
6.4Food
Airline reviews

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

8.0 ExcellentKrishna, Dec 2025
TPA - PHX
Read more American Airlines reviews

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

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

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

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)