PDX - EYW

$207 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 7/29. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% 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.

Flights Deals
Useful Info
Flights 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

Sun, Aug 17 - Fri, Aug 29
United Airlines Logo
6:43 pm - 12:15 pmPDX-EYW
14h 32m2 stops
United Airlines Logo
2:45 pm - 3:25 pmEYW-PDX
27h 40m2 stops
$384United Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
American Airlines Logo
11:08 pm - 11:07 amPDX-EYW
8h 59m1 stop
American Airlines Logo
3:55 pm - 11:16 pmEYW-PDX
10h 21m1 stop
$389American Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
United Airlines Logo
7:10 am - 12:15 pmPDX-EYW
26h 05m2 stops
United Airlines Logo
4:05 pm - 10:08 pmEYW-PDX
9h 03m1 stop
$391United Airlines
Find Deal
Sat, Dec 6 - Wed, Dec 10
American Airlines Logo
11:59 pm - 3:11 pmPDX-EYW
12h 12m2 stops
American Airlines Logo
12:07 pm - 7:27 pmEYW-PDX
10h 20m2 stops
$399American Airlines
Find Deal
Sat, Jul 19 - Fri, Jul 25
American Airlines Logo
11:07 pm - 1:51 pmPDX-EYW
11h 44m1 stop
American Airlines Logo
12:47 pm - 8:47 pmEYW-PDX
11h 00m1 stop
$432American Airlines
Find Deal
Fri, Sep 12 - Fri, Sep 19
United Airlines Logo
10:44 pm - 8:00 amPDX-EYW
30h 16m2 stops
United Airlines Logo
6:45 pm - 10:25 pmEYW-PDX
30h 40m2 stops
$435United Airlines
Find Deal
Sat, Jul 19 - Fri, Jul 25
American Airlines Logo
11:07 pm - 1:51 pmPDX-EYW
11h 44m1 stop
American Airlines Logo
11:18 am - 8:47 pmEYW-PDX
12h 29m2 stops
$437American Airlines
Find Deal
Tue, Dec 2 - Fri, Dec 5
Delta Logo
6:04 am - 5:12 pmPDX-EYW
8h 08m1 stop
Delta Logo
6:00 pm - 9:04 amEYW-PDX
18h 04m2 stops
$476Delta
Find Deal
Sat, Aug 16 - Fri, Aug 29
Delta Logo
12:46 am - 5:27 pmPDX-EYW
13h 41m2 stops
Delta Logo
2:00 pm - 7:03 pmEYW-PDX
8h 03m1 stop
$544Delta
Find Deal
Sun, Oct 19 - Sun, Oct 26
Alaska Airlines Logo
4:28 pm - 11:30 amPDX-EYW
16h 02m2 stops
Alaska Airlines Logo
12:11 pm - 9:49 amEYW-PDX
24h 38m2 stops
$984Alaska Airlines
Find Deal
Useful Info

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.

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 August, where tickets cost $341 (return) on average. On the other hand, the most expensive months are June and March, where the average cost of round-trip tickets is $781 and $697 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. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonAugust
High seasonNovember
Cheapest flight$207
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly and prices are also 5% 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 $207 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, SkyTeam, and oneworld are the airline alliances operating flights between Portland and Key West, with oneworld 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 $428 and an overall rating of 8.0, 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.

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.
8.0
DeltaOverall score based on 7946 reviews
7.9Entertainment
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
Airline reviews

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

10.0 ExcellentTim, Jun 2025MSP - BUF
Read more Delta reviews

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

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

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

Smooth flight, especially take off and landing, and great crew on board. Really loved the stroopwaffles!

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.

Would have thought that they would gas up plane before everyone got on board

Fine. On time, cabin service was fine, bag arrived. All good. Flying into DCA so did not collide with any helicopters, which is also good. Horrid incident that could have and should have been prevented.

Standard. No different than a discount carrier on a short trip.

The flights were terribly delayed and then cancelled which forced us booking another night at the hotel. Very poor management from American Airlines

Crew was late. Baggage was late. 2hs inside the plane waiting fro de-icing and traffic. A 3:30hs flight ended up being almost 6hs inside the airplane.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.