PWM - EYW

$171 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
$271
Typical prices: $392-$591
Breeze Airways
Tue 1/30Tue 2/6
PWM - EYW • 1 stop
Cheapest one-way
$171
Typical prices: $218-$319
American Airlines
Tue 1/16
PWM - EYW • 1 stop
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
September
Cheapest • 36% price drop
April
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Philadelphia (PHL)
Cheapest • Avg $458 (round-trip)
Washington, D.C. Reagan-National (DCA)
Shortest trip • 6h 11m (one-way)
Insights
Insights
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We hope you love your trip to Key West!
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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, Jan 30 - Sat, Feb 6
Breeze Airways Logo
6:31 pm - 11:26 amPWM  Portland-EYW Key West
16h 55m1 stop Tampa
Breeze Airways Logo
12:19 pm - 5:51 pmEYW  Key West-PWM Portland
5h 32m1 stop Tampa
$271Breeze Airways
Sat, Jan 30 - Sat, Feb 6
Breeze Airways Logo
12:28 pm - 10:19 amPWM  Portland-EYW Key West
21h 51m2 stops Raleigh-Durham Orlando
Breeze Airways Logo
12:19 pm - 5:51 pmEYW  Key West-PWM Portland
5h 32m1 stop Tampa
$306Breeze Airways
Sat, Dec 19 - Sat, Jan 9
Breeze Airways Logo
7:12 pm - 11:21 amPWM  Portland-EYW Key West
16h 09m1 stop Tampa
Breeze Airways Logo
12:19 pm - 5:51 pmEYW  Key West-PWM Portland
5h 32m1 stop Tampa
$325Breeze Airways
Wed, Jan 13 - Wed, Jan 20
American Airlines Logo
5:00 am - 12:25 pmPWM  Portland-EYW Key West
7h 25m1 stop Washington, D.C. Reagan-National
American Airlines Logo
1:52 pm - 9:29 pmEYW  Key West-PWM Portland
7h 37m1 stop Charlotte Douglas
$341American Airlines
Tue, Jan 12 - Wed, Jan 20
American Airlines Logo
7:00 am - 3:09 pmPWM  Portland-EYW Key West
8h 09m1 stop Charlotte Douglas
American Airlines Logo
5:32 pm - 10:49 pmEYW  Key West-PWM Portland
5h 17m1 stop Philadelphia
$341American Airlines
Tue, Dec 8 - Wed, Dec 16
Delta Logo
6:00 am - 1:11 pmPWM  Portland-EYW Key West
7h 11m1 stop Atlanta Hartsfield-Jackson
Delta Logo
6:06 pm - 11:33 pmEYW  Key West-PWM Portland
5h 27m1 stop Atlanta Hartsfield-Jackson
$341Delta
Wed, Jan 13 - Wed, Jan 20
American Airlines Logo
7:00 am - 1:56 pmPWM  Portland-EYW Key West
6h 56m1 stop Philadelphia
American Airlines Logo
5:32 pm - 10:49 pmEYW  Key West-PWM Portland
5h 17m1 stop Philadelphia
$341American Airlines
Tue, Jan 12 - Wed, Jan 20
Delta Logo
6:17 am - 12:45 pmPWM  Portland-EYW Key West
6h 28m1 stop New York LaGuardia
Delta Logo
7:30 am - 4:26 pmEYW  Key West-PWM Portland
8h 56m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$346Delta
Sat, Nov 28 - Tue, Dec 15
United Airlines Logo
6:00 am - 1:55 pmPWM  Portland-EYW Key West
7h 55m1 stop Newark
United Airlines Logo
12:05 pm - 11:24 pmEYW  Key West-PWM Portland
11h 19m2 stops Chicago O'Hare Intl Newark
$501United Airlines
Sat, Nov 28 - Tue, Dec 15
United Airlines Logo
6:00 am - 1:55 pmPWM  Portland-EYW Key West
7h 55m1 stop Newark
United Airlines Logo
12:05 pm - 11:24 pmEYW  Key West-PWM Portland
11h 19m2 stops Chicago O'Hare Intl Newark
$501United 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 with more confidence.

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

Round-trip flights from Portland to Key West typically range from $392 to $591. The lowest price found in the past 5 days was $271, on Breeze Airways.

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

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Portland to Key West. It’s 12% cheaper than the average day, while Monday is the most expensive, with prices 19% higher.

What’s the cheapest month to fly from Portland to Key West?

•September is the cheapest month to fly from Portland to Key West at $300 round-trip.
•November ($1,456) and August ($834) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 385% 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

$171
Beat the crowds with an average 80% drop in travelers.
The most popular month to fly with an average 91% increase in travelers.
One-way 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 answers about this route, including flight times, airports, airlines and booking tips.

  • 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.

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

    A nonstop flight from Portland to Key West takes 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.

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

    Round-trip flights from Portland to Key West range from $392 to $591, with an average of $472 over the past 12 months. Anything below $392 counts as a good deal.

  • 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 $271 to $1,928. 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 $290, which is 9% above the typical average for this route.

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

    Key West Airport (EYW) hosts 5 major car rental companies, with daily rates averaging $67 for economy cars. Top options include:

    • Dollar
    • Hertz
    • Budget
    • Enterprise Rent-A-Car
    • Alamo

  • 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).

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

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

    • Atlanta Hartsfield-Jackson (ATL) - 32% of one-stop connections
    • Philadelphia (PHL) - 25% of one-stop connections
    • Charlotte Douglas (CLT) - 20% of one-stop connections
    • Newark (EWR) - 12% of one-stop connections

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

    Yes. Flexible dates can save you up to 26% on flights from Portland to Key West. 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.

  • 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 11m, compared with 6h 29m via Philadelphia (PHL) and 6h 36m via Charlotte Douglas (CLT).

  • 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.

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 are flexible, aim for a Wednesday departure and avoid flying on Monday. On this route, Wednesday flights average $416, about $146 less than Monday fares (26% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Portland to Key West trip for September. Fares historically average $300 round-trip in that month - typically $1,156 less than the most expensive month, which is November (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.

    • Parrot Key Hotel & Villas
    • Margaritaville Beach House Key West
    • Havana Cabana at Key West

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