PDX - EYW

$168 Find Cheap Flights from Portland to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Key West departing on 10/25. 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

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

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

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

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

Fri, Jan 9 - Tue, Jan 13
United Airlines Logo
11:05 pm - 1:02 pmPDX-EYW
10h 57m1 stop
United Airlines Logo
4:15 pm - 10:32 pmEYW-PDX
9h 17m1 stop
$384United Airlines
Find Deal
Fri, Jan 9 - Tue, Jan 13
American Airlines Logo
7:59 am - 11:59 pmPDX-EYW
13h 00m2 stops
American Airlines Logo
3:49 pm - 9:11 pmEYW-PDX
8h 22m1 stop
$437American Airlines
Find Deal
Fri, Jan 9 - Tue, Jan 13
American Airlines Logo
10:15 pm - 1:06 pmPDX-EYW
11h 51m2 stops
American Airlines Logo
6:31 am - 4:28 pmEYW-PDX
12h 57m2 stops
$442American Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
10:55 pm - 11:00 amPDX-EYW
9h 05m1 stop
American Airlines Logo
1:24 pm - 8:17 pmEYW-PDX
9h 53m1 stop
$475American Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
5:22 am - 6:35 pmPDX-EYW
10h 13m2 stops
American Airlines Logo
1:24 pm - 8:17 pmEYW-PDX
9h 53m1 stop
$480American Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
9:07 am - 11:59 pmPDX-EYW
11h 52m2 stops
American Airlines Logo
6:31 am - 4:57 pmEYW-PDX
13h 26m2 stops
$485American Airlines
Find Deal
Mon, Oct 13 - Mon, Oct 20
Delta Logo
10:10 pm - 11:27 amPDX-EYW
10h 17m1 stop
Delta Logo
1:57 pm - 10:08 pmEYW-PDX
11h 11m1 stop
$511Delta
Find Deal
Mon, Oct 13 - Mon, Oct 20
Delta Logo
8:05 pm - 11:27 amPDX-EYW
12h 22m2 stops
Delta Logo
1:57 pm - 7:06 pmEYW-PDX
8h 09m1 stop
$534Delta
Find Deal
Mon, Sep 29 - Mon, Oct 6
Delta Logo
10:05 pm - 10:55 amPDX-EYW
9h 50m1 stop
Delta Logo
1:57 pm - 10:08 pmEYW-PDX
11h 11m1 stop
$557Delta
Find Deal
Tue, Feb 24 - Fri, Feb 27
United Airlines Logo
10:56 pm - 12:46 pmPDX-EYW
10h 50m1 stop
United Airlines Logo
3:56 pm - 1:44 pmEYW-PDX
24h 48m2 stops
$597United Airlines
Find Deal

Everything you should know

Top airlines
United Airlines
Cheapest • from $384 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
4 weeks
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 33% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$384
Typical prices: $330-619
United Airlines
Fri 1/9Tue 1/13
PDX - EYW • 1 stop
Cheapest one-way
$168
Typical prices: $448-505
Multiple Airlines
Sat 10/25
PDX - EYW • 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 Key West!
Booking Insights

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

Get data-powered insights and trends into flights from Portland to Key West to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland to Key West?

What’s the cheapest day of the week to fly from Portland to Key West?

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

When flying from Portland to Key West, you should consider leaving on a Monday and avoid Fridays if you are looking for the best rates. For your return to Portland, you’ll find the best rates on Thursdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Portland to Key West?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Key West, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Key West is September, where tickets cost $414 (return) on average. On the other hand, the most expensive months are June and August, where the average cost of round-trip tickets is $968 and $848 respectively.

How far in advance should I book a flight from Portland to Key West?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Key West, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Key West, you should book around 4 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$168
Best time to beat the crowds but there is an average 36% increase in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Portland to Key West

When to book flights from Portland to Key West

Are your dates flexible? Find out the best times to travel from Portland to Key West 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 Portland to Key West

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

    In the last 3 days, the lowest price for a flight from Portland to Key West was $168 for a one-way ticket and $384 for a round-trip.

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

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

  • Which airports will I be using when flying from Portland to Key West?

    When flying out of Portland you will be using Portland. You will be landing at Key West, also known as Key West.

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

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

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

    Star Alliance, oneworld, and SkyTeam are the airline alliances operating flights between Portland and Key West, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Portland to Key West, Delta or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Key West are Delta and United Airlines. With an average price for the route of $610 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $622 and an overall rating of 7.4.

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

    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 Portland to Key West.

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

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

    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 Key West with an airline and back to Portland with another airline. Booking your flights between Portland and EYW 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 Portland to Key West?

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

Reviews of the top 3 airlines serving from Portland to Key West

 
See real verified KAYAK customer reviews for airlines flying from Portland to Key West. 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 Portland to Key West? 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.
7.9
DeltaOverall score based on 7954 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
8.2Boarding
Airline reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

10.0 ExcellentAnonymous, Sep 2025CLT - BOS
Read more Delta reviews

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Crew was friendly Love the entertainment in the seat head rest.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

This was a code share Latam Airlines flight - everything very good except there was no seatback entertainment

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

It is clear that someone knew, and competent, is in charge of food at United Airlines at least for the international flights. I was flying in coach, but the choices of the dinner were excellent. Tasty, and appropriate size. I had the beef, which was a little bit like a shepherds pie, and it was good. Nothing comparable has been served on a United flight in years. It will not be confused with three star food, but it is very good for airline food. Even better was the breakfast choice between a cinnamon roll and a breakfast sandwich. I chose the breakfast sandwich which was absolutely delicious and which I would happily order again at my local Starbucks or Panera. It is clear that someone knew indifferent is in charge of the food and it’s about time.

Flight was delayed not sure why no explanation given and no apologies either. Otherwise the flight was fine

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

Flight delays numerous times. Everytime we would get close to boarding it would be delayed again. Strung along the entire time.

This flight never occurred because AA couldn’t get their act together.

During service there was a garbage/beverage spill near our seats that never was cleaned up. On a relatively short flight when we’re fortunate enough to actually have in flight movies available, the flight attendants pitching the AADVANTAGE credit card shouldn’t talk for the last 10 minutes of the flight so that we miss the end of the movie.

Waited on the runway for takeoff for 2.5 hours. Air traffic rerouted us. The plane didn't have enough fuel, so had to go back to the gate. Had to wait for a new pilot. Should have landed at 5:22. Didn't land until 9:10. Trash flight.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

The boarding was pretty easy. However, the first class seats are not lay flat as other airlines (like JetBlue) has and therefore sleeping was a challenge.

Everything about the flight was lovely…We left early, arrived early, cabin crew were efficient and helpful. Flight was easy and most pleasant.

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

Information on your arrival and departure airports

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