$334 Find Cheap Flights from Key West to Oregon

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Oregon departing on 5/14. 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 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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

Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:52 pm
EYW
-
PDX
10h 54m
1 stop
American Airlines Logo
11:30 pm - 4:12 pm
PDX
-
EYW
13h 42m
2 stops
$334American Airlines
Thu, Mar 5 - Wed, Mar 11
American Airlines Logo
2:06 pm - 8:44 pm
EYW
-
PDX
9h 38m
1 stop
American Airlines Logo
5:40 am - 4:24 pm
PDX
-
EYW
7h 44m
1 stop
$356American Airlines
Fri, Feb 13 - Tue, Feb 17
United Airlines Logo
3:56 pm - 10:40 pm
EYW
-
PDX
9h 44m
1 stop
United Airlines Logo
10:38 pm - 1:15 pm
PDX
-
EYW
11h 37m
1 stop
$389United Airlines
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
2:06 pm - 8:44 pm
EYW
-
PDX
9h 38m
1 stop
American Airlines Logo
6:40 am - 10:22 pm
PDX
-
EYW
12h 42m
2 stops
$394American Airlines
Fri, Feb 13 - Tue, Feb 17
American Airlines Logo
2:06 pm - 12:17 am
EYW
-
PDX
13h 11m
2 stops
American Airlines Logo
6:40 am - 10:22 pm
PDX
-
EYW
12h 42m
2 stops
$399American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
3:58 pm - 11:52 pm
EYW
-
PDX
10h 54m
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 - 11:52 pm
EYW
-
PDX
10h 54m
1 stop
American Airlines Logo
10:30 pm - 1:42 pm
PDX
-
EYW
12h 12m
1 stop
$427American Airlines
Thu, Mar 5 - Wed, Mar 11
American Airlines Logo
2:06 pm - 8:44 pm
EYW
-
PDX
9h 38m
1 stop
American Airlines Logo
6:40 am - 10:37 pm
PDX
-
EYW
12h 57m
2 stops
$462American 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
10:59 pm - 11:15 am
PDX
-
EYW
9h 16m
1 stop
$486American Airlines
Thu, May 14 - Sat, May 23
American Airlines Logo
1:36 pm - 10:49 pm
EYW
-
PDX
12h 13m
2 stops
American Airlines Logo
11:59 pm - 4:12 pm
PDX
-
EYW
13h 13m
2 stops
$487American Airlines
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.

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

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 Oregon were found on American Airlines ($334) and United Airlines ($389).

Find deals

Good to know

Cheapest flight$334
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.

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 11205 reviews
7.5Boarding
7.2Comfort
8.0Crew
6.9Entertainment
6.4Food
Airline reviews

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

10.0 ExcellentCindy, Jan 2026
MIA - BHM
Read more American Airlines reviews

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.

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.

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

Information on your arrival and departure airports

Key West (EYW)