PWM - EYW

$182 Find Cheap Flights from Portland to Key West - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$265
Typical prices: $391-$594
Breeze Airways
Wed 11/7Sun 11/11
PWM - EYW • 1 stop
Cheapest one-way
$182
Typical prices: $213-$319
Multiple Airlines
Sun 11/18
PWM - EYW • 2 stops
Nonstop flights
Not available
There are currently no direct flights between Portland and Key West. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
October
Cheapest • 15% price drop
April
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Philadelphia (PHL)
Cheapest • Avg $514 (round-trip)
Washington, D.C. Reagan-National (DCA)
Shortest trip • 6h 10m (one-way)
Insights
Insights
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We hope you love your trip to Key West!
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Booking Insights
Flight Deals

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

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to Key West

Sat, Nov 7 - Wed, Nov 11
Breeze Airways Logo
6:31 pm - 11:21 amPWM  Portland-EYW Key West
16h 50m1 stop Tampa
Breeze Airways Logo
10:04 am - 5:51 pmEYW  Key West-PWM Portland
7h 47m1 stop Tampa
$265Breeze Airways
Sat, Jan 16 - Wed, Jan 20
Multiple Airlines Logo
6:31 pm - 2:35 pmPWM  Portland-EYW Key West
20h 04m1 stop Tampa
Multiple Airlines Logo
12:19 pm - 5:51 pmEYW  Key West-PWM Portland
5h 32m1 stop Tampa
$293Multiple Airlines
Wed, Jan 13 - Wed, Jan 20
American Airlines Logo
5:10 am - 12:33 pmPWM  Portland-EYW Key West
7h 23m1 stop Washington, D.C. Reagan-National
American Airlines Logo
5:32 pm - 10:46 pmEYW  Key West-PWM Portland
5h 14m1 stop Philadelphia
$301American Airlines
Tue, Jan 12 - Wed, Jan 20
American Airlines Logo
7:00 am - 3:11 pmPWM  Portland-EYW Key West
8h 11m1 stop Charlotte Douglas
American Airlines Logo
5:32 pm - 10:46 pmEYW  Key West-PWM Portland
5h 14m1 stop Philadelphia
$301American Airlines
Tue, Jan 12 - Wed, Jan 20
American Airlines Logo
7:00 am - 1:11 pmPWM  Portland-EYW Key West
6h 11m1 stop Charlotte Douglas
American Airlines Logo
1:52 pm - 9:36 pmEYW  Key West-PWM Portland
7h 44m1 stop Charlotte Douglas
$301American Airlines
Wed, Jan 13 - Wed, Jan 20
Delta Logo
6:00 am - 1:37 pmPWM  Portland-EYW Key West
7h 37m1 stop New York LaGuardia
Delta Logo
7:00 am - 4:59 pmEYW  Key West-PWM Portland
9h 59m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$306Delta
Tue, Jan 12 - Wed, Jan 20
Delta Logo
6:00 am - 1:37 pmPWM  Portland-EYW Key West
7h 37m1 stop New York LaGuardia
Delta Logo
7:00 am - 4:59 pmEYW  Key West-PWM Portland
9h 59m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$306Delta
Sat, Nov 7 - Wed, Nov 11
Multiple Airlines Logo
6:31 pm - 11:21 amPWM  Portland-EYW Key West
16h 50m1 stop Tampa
Multiple Airlines Logo
12:54 pm - 2:25 pmEYW  Key West-PWM Portland
25h 31m2 stops Tampa St. Petersburg Pittsburgh
$313Multiple Airlines
Sat, Oct 24 - Wed, Oct 28
United Airlines Logo
6:00 am - 3:24 pmPWM  Portland-EYW Key West
9h 24m1 stop Chicago O'Hare Intl
United Airlines Logo
2:51 pm - 11:21 pmEYW  Key West-PWM Portland
8h 30m1 stop Newark
$529United Airlines
Sat, Oct 24 - Wed, Oct 28
United Airlines Logo
5:15 am - 3:24 pmPWM  Portland-EYW Key West
10h 09m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl
United Airlines Logo
2:51 pm - 11:21 pmEYW  Key West-PWM Portland
8h 30m1 stop Newark
$534United Airlines
Booking Insights

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

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

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

Round-trip flights from Portland to Key West start at $265. Prices are below average for this route right now, with typical round-trip fares ranging from $391 to $594. The lowest price found in the past 5 days was $265 on Breeze Airways.

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

Wednesday is the cheapest day of the week to fly from Portland to Key West, it is 16% cheaper than the average day. Monday is the most expensive day with flight prices 14% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is the cheapest month to fly from Portland to Key West?

  • October is the cheapest month to fly from Portland to Key West at $416 round-trip.
  • August ($834) and July ($736) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 100% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Portland to Key West flights

Low season

August

Cheapest flight

$182
Best time to beat the crowds but there is an average 70% increase in price.
Most popular time to fly with an average 21% increase in price.
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

Your Portland to Key West 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 Portland to Key West?

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

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

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

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

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

    • Philadelphia (PHL) - 34% of one-stop connections
    • Charlotte Douglas (CLT) - 24% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 21% of one-stop connections
    • Newark (EWR) - 13% 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 Portland to Key West?

    Yes. Being flexible with your travel dates can save you up to 26% on the Portland to Key West route. Wednesday is the cheapest departure day at $416 round-trip on average, while Monday is the most expensive at $562, a difference of $146. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Key West?

    Some of the most popular sights in Key West are Duval Street, Key West Historic District and Mallory Square. These are among the most viewed places in Key West on KAYAK.

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

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

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

    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 Portland to Key West 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 $2,230. That means the highest observed fare was about 7x higher than the lowest one.

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

    One-way fares from Portland to Key West are currently higher than usual. Average one-way flight prices are about $302, which is 16% above the typical average for this route.

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

    Flying via Washington, D.C. Reagan-National (DCA) gives the shortest average 1-stop total travel time at 6h 10m, compared with 6h 26m via Charlotte Douglas (CLT) and 6h 30m via Philadelphia (PHL).

  • What car rental options are available at Key West Airport (EYW)?

    Key West Airport (EYW) hosts 5 major car rental companies, with daily rates starting from around $29 for economy cars. Top options include:
    • Dollar
    • Hertz
    • Budget
    • Enterprise Rent-A-Car
    • Alamo

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

    Round-trip flights from Portland to Key West range from $391 to $594, with an average of $490 over the past 12 months. Anything below $391 counts as a good deal.

Your guide to booking Portland to Key West 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 Wednesday departure instead of Monday. On this route, Wednesday flights average $416 - about $146 less than Monday (26% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Portland to Key West trip for October. Fares historically average $416 round-trip in that month - typically $418 less than the most expensive month, which is August (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Key West Airport.
    - Havana Cabana at Key West
    - Fairfield Inn & Suites by Marriott Key West at The Keys Collection
    - Parrot Key Hotel & Villas

More options for your flight from Portland to Key West

Complete your trip to Key West with a hotel stay or car rental

Car rentals in Key West
Hotels in Key West
Vacations in Key West