EYW - PWM

$197 Find Cheap Flights from Key West to Portland - 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 Key West to Portland departing on 10/17. 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
$301
American Airlines
Wed 10/21Tue 10/27
EYW - PWM • 1 stop
Cheapest one-way
$197
Breeze Airways
Sat 10/17
EYW - PWM • 1 stop
Top airlines
Cheapest • from $301 (round-trip)
Best reviews • 7.1 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Key West and Portland. You'll need at least 1 connection.
Insights
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Insights
Top layover airports
Cheapest • Avg $328 (round-trip)
Shortest trip • 6h 06m (one-way)
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Flight 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, Oct 21 - Tue, Oct 27
American Airlines Logo
5:34 pm - 11:41 pm
EYW
-
PWM
6h 07m
1 stop
American Airlines Logo
7:00 am - 1:54 pm
PWM
-
EYW
6h 54m
1 stop
$301American Airlines
Tue, Oct 20 - Wed, Oct 28
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Tue, Oct 20 - Tue, Oct 27
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Sun, Oct 18 - Thu, Oct 22
Multiple Airlines Logo
10:59 am - 9:08 am
EYW
-
PWM
22h 09m
1 stop
Multiple Airlines Logo
3:10 pm - 5:47 pm
PWM
-
EYW
26h 37m
1 stop
$301Multiple Airlines
Wed, Oct 21 - Wed, Oct 28
Delta Logo
7:40 am - 1:02 pm
EYW
-
PWM
5h 22m
1 stop
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$301Delta
Wed, Oct 14 - Tue, Oct 20
Delta Logo
6:10 pm - 11:35 pm
EYW
-
PWM
5h 25m
1 stop
Delta Logo
6:04 am - 8:01 pm
PWM
-
EYW
13h 57m
2 stops
$306Delta
Wed, Oct 21 - Wed, Oct 28
Delta Logo
7:40 am - 4:02 pm
EYW
-
PWM
8h 22m
2 stops
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$306Delta
Tue, Oct 20 - Tue, Oct 27
Delta Logo
2:00 pm - 11:18 pm
EYW
-
PWM
9h 18m
2 stops
Delta Logo
2:09 pm - 8:01 pm
PWM
-
EYW
5h 52m
1 stop
$306Delta
Fri, Oct 16 - Thu, Oct 22
Multiple Airlines Logo
12:59 pm - 5:51 pm
EYW
-
PWM
28h 52m
1 stop
Multiple Airlines Logo
3:10 pm - 5:47 pm
PWM
-
EYW
26h 37m
1 stop
$306Multiple Airlines
Tue, Oct 20 - Fri, Oct 30
American Airlines Logo
2:15 pm - 9:51 pm
EYW
-
PWM
7h 36m
1 stop
American Airlines Logo
12:06 pm - 6:49 pm
PWM
-
EYW
6h 43m
1 stop
$335American Airlines
Booking Insights

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.

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

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Key West to Portland were found on Delta ($301) and Breeze Airways ($329).

Good to know

Cheapest flight

$197
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 5 days, the lowest price for a flight from Key West to Portland was $197 for a one-way ticket and $301 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?

    oneworld is the only airline alliance operating flights between Key West and Portland.

  • 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.

Reviews of the 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.
7.1
American AirlinesOverall score based on 11839 reviews
6.8Entertainment
6.4Food
7.5Boarding
7.2Comfort
7.9Crew
Airline reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

10.0 ExcellentSergio, Jul 2026
MIA - DCA
Read more American Airlines reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

I have never been assaulted they way I was today in Charlotte - shame on American

90 min delay for a food cart that needed to be fixed.

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

Information on your arrival and departure airports