EYW - PWM

$138 Find Cheap Flights from Key West to Portland - Compare and Save

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Everything you should know

Cheapest round-trip
$301
Typical prices: $347-$489
American Airlines
Sun 10/21Sat 10/27
EYW - PWM • 1 stop
Cheapest one-way
$138
Typical prices: $208-$490
Breeze Airways
Wed 10/17
EYW - PWM • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Key West and Portland. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
January
Cheapest • 32% price drop
September
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Philadelphia (PHL)
Cheapest • Avg $334 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 6h 26m (one-way)
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Insights
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Flight Deals

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

 
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
4:45 pm - 10:36 pmEYW  Key West-PWM Portland
5h 51m1 stop Charlotte Douglas
American Airlines Logo
7:03 am - 1:35 pmPWM  Portland-EYW Key West
6h 32m1 stop Charlotte Douglas
$301American Airlines
Wed, Oct 21 - Fri, Oct 30
Breeze Airways Logo
10:04 am - 5:51 pmEYW  Key West-PWM Portland
7h 47m1 stop Tampa
Breeze Airways Logo
5:35 pm - 9:24 amPWM  Portland-EYW Key West
15h 49m2 stops Charleston Tampa
$304Breeze Airways
Wed, Oct 21 - Tue, Oct 27
Delta Logo
6:10 pm - 11:35 pmEYW  Key West-PWM Portland
5h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:28 am - 5:15 pmPWM  Portland-EYW Key West
10h 47m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
$306Delta
Wed, Oct 21 - Tue, Oct 27
American Airlines Logo
4:45 pm - 10:36 pmEYW  Key West-PWM Portland
5h 51m1 stop Charlotte Douglas
American Airlines Logo
7:03 am - 1:35 pmPWM  Portland-EYW Key West
6h 32m1 stop Charlotte Douglas
$321American Airlines
Sun, Oct 18 - Fri, Oct 30
Breeze Airways Logo
10:59 am - 9:08 amEYW  Key West-PWM Portland
22h 09m1 stop Orlando
Breeze Airways Logo
5:35 pm - 9:24 amPWM  Portland-EYW Key West
15h 49m2 stops Charleston Tampa
$321Breeze Airways
Wed, Oct 21 - Tue, Oct 27
Delta Logo
6:10 pm - 11:35 pmEYW  Key West-PWM Portland
5h 25m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:28 am - 5:15 pmPWM  Portland-EYW Key West
10h 47m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
$326Delta
Mon, Oct 19 - Fri, Oct 30
Breeze Airways Logo
11:59 am - 4:24 pmEYW  Key West-PWM Portland
28h 25m1 stop Raleigh-Durham
Breeze Airways Logo
5:35 pm - 9:24 amPWM  Portland-EYW Key West
15h 49m2 stops Charleston Tampa
$332Breeze Airways
Tue, Oct 20 - Fri, Oct 30
Breeze Airways Logo
1:16 pm - 5:51 pmEYW  Key West-PWM Portland
28h 35m1 stop Tampa
Breeze Airways Logo
5:35 pm - 9:24 amPWM  Portland-EYW Key West
15h 49m2 stops Charleston Tampa
$332Breeze Airways
Wed, Oct 21 - Fri, Oct 30
Breeze Airways Logo
10:04 am - 5:51 pmEYW  Key West-PWM Portland
7h 47m1 stop Tampa
Breeze Airways Logo
5:35 pm - 9:24 amPWM  Portland-EYW Key West
15h 49m2 stops Charleston Tampa
$333Breeze Airways
Tue, Oct 20 - Fri, Oct 30
American Airlines Logo
2:15 pm - 9:51 pmEYW  Key West-PWM Portland
7h 36m1 stop Charlotte Douglas
American Airlines Logo
6:00 am - 12:27 pmPWM  Portland-EYW Key West
6h 27m1 stop Charlotte Douglas
$356American Airlines
Booking Insights

Price, demand and travel trends for Key West to Portland flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Key West to Portland with more confidence.

How much is a round-trip flight from Key West to Portland?

Round-trip flights from Key West to Portland start at $301. Prices are below average for this route right now, with typical round-trip fares ranging from $347 to $489. The lowest price found in the past 5 days was $301 on American Airlines.

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Key details for Key West to Portland flights

Low season

May

Cheapest flight

$138
Best time to beat the crowds but there is an average 42% increase in price.
Most popular time to fly and prices are also 5% 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

Your Key West to Portland flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Key West to Portland?

    Flights from Key West to Portland usually depart from Key West (EYW) and arrive at Portland (PWM).

  • What cabin classes can I book on flights from Key West to Portland?

    Only Economy Class is available on flights from Key West to Portland.

  • Which airports do connecting flights from Key West to Portland pass through?

    One-stop flights from Key West to Portland most commonly connect through:

    • Philadelphia (PHL) - 58% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 32% of one-stop connections
    • Charlotte Douglas (CLT) - 11% of one-stop connections

    Philadelphia (PHL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Key West to Portland?

    Yes. Being flexible with your travel dates can save you up to 29% on the Key West to Portland route. Thursday is the cheapest departure day at $348 round-trip on average, while Tuesday is the most expensive at $489, a difference of $141. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How long is a flight from Key West to Portland?

    A nonstop flight from Key West to Portland takes 0h 00m, covering 1,468 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Key West to Portland changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $301 to $1,498. That means the highest observed fare was about 5x higher than the lowest one.

  • How are flight prices from Key West to Portland looking right now?

    One-way fares from Key West to Portland are currently in line with typical prices for this route. Average one-way fares are about $362.

  • How much time can I save by choosing a different layover airport from Key West to Portland?

    Flying via Philadelphia (PHL) gives the shortest average 1-stop total travel time at 6h 16m, compared with 6h 26m via Atlanta Hartsfield-Jackson (ATL) and 7h 22m via Charlotte Douglas (CLT).

  • What car rental options are available at Portland Airport (PWM)?

    Portland Airport (PWM) hosts 5 major car rental companies, with daily rates starting from around $24 for economy cars. Top options include:
    • Dollar
    • Budget
    • Alamo
    • Hertz
    • Movly

  • How much should I expect to pay for a Key West to Portland flight?

    Round-trip flights from Key West to Portland range from $347 to $489, with an average of $408 over the past 12 months. Anything below $347 counts as a good deal.

Your guide to booking Key West to Portland flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Thursday departure instead of Tuesday. On this route, Thursday flights average $348 - about $141 less than Tuesday (29% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Key West to Portland trip for January. Fares historically average $276 round-trip in that month - typically $303 less than the most expensive month, which is May (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Portland Airport.
    - Clarion Hotel Portland Airport Me
    - La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
    - DoubleTree by Hilton Portland

More options for your flight from Key West to Portland

Complete your trip to Portland with a hotel stay or car rental

Car rentals in Portland
Hotels in Portland
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