EYW - PWM

$168 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 4/15. 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

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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$311
Breeze Airways
Thu 3/26Mon 3/30
EYW - PWM • 1 stop
Cheapest one-way
$168
Typical prices: $192-$342
Breeze Airways
Wed 4/15
EYW - PWM • 2 stops
Top airlines
Cheapest • from $311 (round-trip)
Best reviews • 7.9 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
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $314 (round-trip)
Shortest trip • 6h 04m (one-way)
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Flight Deals
Booking Insights
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

Thu, Mar 26 - Mon, Mar 30
Breeze Airways Logo
9:46 am - 9:07 am
EYW
-
PWM
23h 21m
1 stop
Breeze Airways Logo
5:06 pm - 12:21 pm
PWM
-
EYW
19h 15m
2 stops
$311Breeze Airways
Thu, Mar 26 - Mon, Mar 30
American Airlines Logo
5:04 pm - 10:59 pm
EYW
-
PWM
5h 55m
1 stop
American Airlines Logo
6:00 am - 12:00 pm
PWM
-
EYW
6h 00m
1 stop
$337American Airlines
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
4:40 pm - 10:50 pm
EYW
-
PWM
6h 10m
1 stop
American Airlines Logo
7:00 am - 1:45 pm
PWM
-
EYW
6h 45m
1 stop
$418American Airlines
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
3:56 pm - 10:50 pm
EYW
-
PWM
6h 54m
2 stops
American Airlines Logo
7:00 am - 1:45 pm
PWM
-
EYW
6h 45m
1 stop
$423American Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
12:25 pm - 10:17 am
EYW
-
PWM
21h 52m
2 stops
Multiple Airlines Logo
6:18 pm - 3:42 pm
PWM
-
EYW
21h 24m
1 stop
$425Multiple Airlines
Fri, May 8 - Tue, May 12
American Airlines Logo
3:58 pm - 10:46 pm
EYW
-
PWM
6h 48m
2 stops
American Airlines Logo
10:48 am - 10:58 pm
PWM
-
EYW
12h 10m
2 stops
$429American Airlines
Tue, Mar 31 - Sat, Apr 4
American Airlines Logo
5:19 pm - 11:55 pm
EYW
-
PWM
6h 36m
1 stop
American Airlines Logo
7:00 am - 1:59 pm
PWM
-
EYW
6h 59m
1 stop
$493American Airlines
Tue, Mar 31 - Sat, Apr 4
American Airlines Logo
3:20 pm - 11:55 pm
EYW
-
PWM
8h 35m
2 stops
American Airlines Logo
12:44 pm - 10:37 pm
PWM
-
EYW
9h 53m
2 stops
$504American Airlines
Thu, Apr 2 - Mon, Apr 6
Delta Logo
2:40 pm - 11:22 pm
EYW
-
PWM
8h 42m
1 stop
Delta Logo
5:23 am - 1:43 pm
PWM
-
EYW
8h 20m
1 stop
$508Delta
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
4:40 pm - 10:50 pm
EYW
-
PWM
6h 10m
1 stop
American Airlines Logo
7:00 am - 1:45 pm
PWM
-
EYW
6h 45m
1 stop
$539American 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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Portland were found on Breeze Airways ($311) and American Airlines ($337).

Good to know

Cheapest flight$168
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 $168 for a one-way ticket and $311 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, and oneworld are the airline alliances operating flights between Key West and Portland, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Key West to Portland are Delta and American Airlines. With an average price for the route of $353 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $347 and an overall rating of 7.1.

  • 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 airlines 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.
7.9
DeltaOverall score based on 8296 reviews
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
7.9Comfort
Airline reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

2.0 MediocreSusan, Mar 2026
JAX - ATL
Read more Delta reviews

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

The flight was great as well as the airline staff

Comfort seating was on the tight side. Maybe it was a smaller plane(?)

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

There was no beverage service and the only time I saw a crew member walk through the cabin is when we were preparing to land.

Flights were constantly delayed. CRW took 50 minutes to get bags

Where do I start!! I was delayed with my flight from Dallas to Tampa. On the way back from Tampa to Dallas the flight was delayed over 4 hours+. I was put on another flight that was also delayed but not as long. Traveling on American Airlines is becoming exhausing.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

The flight attendants and the service is getting worse by the day.

Other than nearly three hour delay for maintenance issues, everything went smooth

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

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

Information on your arrival and departure airports