EYW - PWM

$189 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 8/6. 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 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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Flights Deals

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

 
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

Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
4:58 pm - 11:19 pmEYW-PWM
6h 21m1 stop
American Airlines Logo
7:23 am - 1:51 pmPWM-EYW
6h 28m1 stop
$269American Airlines
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Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
12:47 pm - 11:19 pmEYW-PWM
10h 32m2 stops
American Airlines Logo
7:23 am - 1:51 pmPWM-EYW
6h 28m1 stop
$274American Airlines
Find Deal
Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
12:47 pm - 11:19 pmEYW-PWM
10h 32m2 stops
American Airlines Logo
7:23 am - 4:18 pmPWM-EYW
8h 55m2 stops
$279American Airlines
Find Deal
Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
4:58 pm - 11:19 pmEYW-PWM
6h 21m1 stop
American Airlines Logo
5:55 am - 4:18 pmPWM-EYW
10h 23m2 stops
$281American Airlines
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Wed, Sep 10 - Fri, Sep 19
Delta Logo
6:20 pm - 12:03 amEYW-PWM
5h 43m1 stop
Delta Logo
12:30 pm - 7:44 pmPWM-EYW
7h 14m1 stop
$348Delta
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Wed, Jul 23 - Wed, Jul 30
American Airlines Logo
1:25 pm - 11:19 pmEYW-PWM
9h 54m2 stops
American Airlines Logo
5:55 am - 4:18 pmPWM-EYW
10h 23m2 stops
$359American Airlines
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Fri, Jul 18 - Sun, Jul 20
American Airlines Logo
4:58 pm - 11:19 pmEYW-PWM
6h 21m1 stop
American Airlines Logo
7:23 am - 1:51 pmPWM-EYW
6h 28m1 stop
$483American Airlines
Find Deal
Wed, Sep 10 - Fri, Sep 19
Breeze Airways Logo
9:47 am - 1:51 pmEYW-PWM
52h 04m3 stops
Breeze Airways Logo
2:36 pm - 10:19 amPWM-EYW
43h 43m3 stops
$757Breeze Airways
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Wed, Aug 13 - Mon, Aug 18
Delta Logo
6:22 pm - 12:03 amEYW-PWM
5h 41m1 stop
Delta Logo
6:00 am - 5:27 pmPWM-EYW
11h 27m2 stops
$1,023Delta
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Wed, Aug 13 - Mon, Aug 18
Delta Logo
6:22 pm - 12:03 amEYW-PWM
5h 41m1 stop
Delta Logo
6:00 am - 1:05 pmPWM-EYW
7h 05m1 stop
$1,143Delta
Find Deal
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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.

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

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

Your flight ticket price will generally be cheaper if you fly to Portland on a Wednesday and more expensive on a Friday. On your return trip to Key West, you should consider flying back on a Tuesday, and avoid Thursdays for better deals.

Find deals

Good to know

Low seasonJuly
High seasonSeptember
Cheapest flight$189
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 19% lower on average.
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 $189 for a one-way ticket and $269 for a round-trip.

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

    No, a passport isn't needed to fly from Key West to Portland. However, local authorities might ask for an official ID.

  • 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?

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

  • 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 PWM 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.

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 10000 reviews
7.5Boarding
8.0Crew
6.5Food
7.2Comfort
6.9Entertainment
Airline reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

2.0 MediocreJose David, Jun 2025MIA - DTW
Read more American Airlines reviews

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

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

Information on your arrival and departure airports

Key West (EYW)
Portland (PWM)

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