PDX - EYW

$140 Find Cheap Flights from Portland to Key West - Compare and Save

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 8/29. 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, 0 bags

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Everything you should know

Cheapest round-trip
$439
Typical prices: $428-$711
Delta
Tue 11/17Wed 11/25
PDX - EYW • 1 stop
Cheapest one-way
$140
Multiple Airlines
Sat 8/29
PDX - EYW • 2 stops
Top airlines
Cheapest • from $439 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and Key West. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $397 (round-trip)
Shortest trip • 7h 38m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 36% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Key West!
Flight Deals
Booking Insights
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

Tue, Nov 17 - Wed, Nov 25
Delta Logo
6:50 am - 8:02 pm-
10h 12m
Delta Logo
2:00 pm - 9:52 pm-
10h 52m
$439Delta
Sat, Nov 7 - Wed, Nov 18
Delta Logo
7:00 am - 8:01 pm-
10h 01m
Delta Logo
7:35 am - 1:14 pm-
8h 39m
$439Delta
Sat, Nov 7 - Wed, Nov 18
American Airlines Logo
5:00 am - 4:55 pm-
8h 55m
American Airlines Logo
2:26 pm - 7:32 pm-
8h 06m
$439American Airlines
Wed, Nov 18 - Tue, Nov 24
American Airlines Logo
5:00 am - 4:55 pm-
8h 55m
American Airlines Logo
4:43 pm - 12:12 am-
10h 29m
$439American Airlines
Tue, Dec 1 - Sat, Dec 5
United Airlines Logo
10:59 pm - 11:11 am-
9h 12m
United Airlines Logo
4:05 pm - 11:12 pm-
10h 07m
$445United Airlines
Wed, Nov 18 - Wed, Nov 25
Delta Logo
11:10 pm - 10:48 am-
8h 38m
Delta Logo
2:00 pm - 9:52 pm-
10h 52m
$469Delta
Tue, Oct 20 - Wed, Oct 28
Delta Logo
6:50 am - 8:01 pm-
10h 11m
Delta Logo
7:40 am - 1:38 pm-
8h 58m
$488Delta
Sat, Jan 9 - Wed, Jan 13
United Airlines Logo
10:59 pm - 11:11 am-
9h 12m
United Airlines Logo
4:05 pm - 11:12 pm-
10h 07m
$489United Airlines
Sun, Jan 17 - Sat, Jan 23
American Airlines Logo
10:55 pm - 12:33 pm-
10h 38m
American Airlines Logo
1:22 pm - 8:24 pm-
10h 02m
$492American Airlines
Sat, Sep 19 - Sat, Sep 26
United Airlines Logo
11:09 pm - 1:29 pm-
11h 20m
United Airlines Logo
4:00 pm - 10:23 pm-
9h 23m
$533United Airlines
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.

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 April, where tickets cost $428 (return) on average. On the other hand, the most expensive months are October and June, where the average cost of round-trip tickets is $916 and $834 respectively.

Good to know

Low season

September

Cheapest flight

$140
Best time to beat the crowds with an average 6% 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 5 days, the lowest price for a flight from Portland to Key West was $140 for a one-way ticket and $439 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?

    SkyTeam, and oneworld 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 American Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to Key West are Delta and American Airlines. With an average price for the route of $640 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $621 and an overall rating of 7.1.

  • 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 airlines flying 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.
7.8
DeltaOverall score based on 8491 reviews
8.1Boarding
7.2Food
7.8Entertainment
8.5Crew
7.8Comfort
Airline reviews

We got stuck on the tarmac taxiing after landing early so we didn’t get off the plane until an hour later than we thought we would

2.0 MediocreAlyssa, Jul 2026
Read more Delta reviews

We got stuck on the tarmac taxiing after landing early so we didn’t get off the plane until an hour later than we thought we would

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Second flight in a row where the entertainment system is broken. 5 hour long flight with no entertainment and flight attendants did not seem interested in resolving the matter. Very shocked to be treated this poorly considering I paid for a first class experience and have Diamond Medallion status.

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

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.

My seat had no padding, it was literally plywood with a plastic cover. I could not change seats on my 10 hour flight. My excitement for this trip helped me deal with the pain.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

The flights were on time- Great service Would have liked more options for food choices.

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

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

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

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We sat on the plane for 1 hour because the airline was short handed could not be unloading.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

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

Information on your arrival and departure airports