PDX - EYW

$236 Find Cheap Flights from Portland to Key West - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$459
Typical prices: $464-$783
American Airlines
Tue 1/23Tue 1/30
PDX - EYW • 1 stop
Cheapest one-way
$236
Typical prices: $457-$555
Multiple Airlines
Mon 10/1
PDX - 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
April
Cheapest • 31% price drop
April
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Newark (EWR)
Cheapest • Avg $397 (round-trip)
Dallas/Fort Worth (DFW)
Shortest trip • 8h 38m (one-way)
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 Key West!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Key West (PDX-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 23 - Sat, Jan 30
American Airlines Logo
11:00 pm - 1:11 pmPDX  Portland-EYW Key West
11h 11m1 stop Charlotte Douglas
American Airlines Logo
5:52 pm - 12:16 amEYW  Key West-PDX Portland
9h 24m1 stop Miami
$459American Airlines
Sat, Oct 24 - Sat, Oct 31
American Airlines Logo
5:20 am - 4:54 pmPDX  Portland-EYW Key West
8h 34m1 stop Dallas/Fort Worth
American Airlines Logo
2:34 pm - 9:15 pmEYW  Key West-PDX Portland
9h 41m1 stop Dallas/Fort Worth
$459American Airlines
Tue, Jan 26 - Mon, Feb 1
American Airlines Logo
11:05 pm - 9:22 amPDX  Portland-EYW Key West
7h 17m1 stop Miami
American Airlines Logo
5:52 pm - 12:16 amEYW  Key West-PDX Portland
9h 24m1 stop Miami
$463American Airlines
Sat, Dec 12 - Thu, Dec 17
American Airlines Logo
11:09 pm - 11:54 amPDX  Portland-EYW Key West
9h 45m1 stop Chicago O'Hare Intl
American Airlines Logo
5:16 pm - 12:09 amEYW  Key West-PDX Portland
9h 53m1 stop Chicago O'Hare Intl
$463American Airlines
Sat, Feb 13 - Wed, Feb 17
United Airlines Logo
10:59 pm - 11:11 amPDX  Portland-EYW Key West
9h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
4:00 pm - 11:07 pmEYW  Key West-PDX Portland
10h 07m1 stop Chicago O'Hare Intl
$509United Airlines
Sat, Oct 10 - Sat, Oct 17
Delta Logo
11:00 pm - 10:47 amPDX  Portland-EYW Key West
8h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:40 am - 1:38 pmEYW  Key West-PDX Portland
8h 58m1 stop Atlanta Hartsfield-Jackson
$547Delta
Fri, Feb 12 - Wed, Feb 17
United Airlines Logo
10:59 pm - 11:11 amPDX  Portland-EYW Key West
9h 12m1 stop Chicago O'Hare Intl
United Airlines Logo
4:00 pm - 11:07 pmEYW  Key West-PDX Portland
10h 07m1 stop Chicago O'Hare Intl
$549United Airlines
Sat, Feb 13 - Wed, Feb 17
United Airlines Logo
7:30 am - 11:11 amPDX  Portland-EYW Key West
24h 41m2 stops San Francisco Chicago O'Hare Intl
United Airlines Logo
4:00 pm - 11:07 pmEYW  Key West-PDX Portland
10h 07m1 stop Chicago O'Hare Intl
$568United Airlines
Sat, Oct 10 - Sat, Oct 17
Delta Logo
11:00 pm - 10:47 amPDX  Portland-EYW Key West
8h 47m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:00 pm - 7:09 pmEYW  Key West-PDX Portland
8h 09m1 stop Atlanta Hartsfield-Jackson
$619Delta
Sun, Feb 14 - Thu, Feb 18
Delta Logo
9:45 pm - 10:58 amPDX  Portland-EYW Key West
10h 13m1 stop Atlanta Hartsfield-Jackson
Delta Logo
2:35 pm - 10:26 pmEYW  Key West-PDX Portland
10h 51m1 stop Atlanta Hartsfield-Jackson
$645Delta
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 $459. Prices are below average for this route right now, with typical round-trip fares ranging from $464 to $783. The lowest price found in the past 5 days was $459 on American Airlines.

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 25% cheaper than the average day. Sunday is the most expensive day with flight prices 48% 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?

•April is the cheapest month to fly from Portland to Key West at $428 round-trip.
•October ($914) and June ($866) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 113% 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

$236
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 31% lower on average.
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 (PDX) and arrive at Key West (EYW).

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

    Two cabin classes are available on flights from Portland to Key West:

    • Economy Class
    • First Class

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

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

    • Dallas/Fort Worth (DFW) - 54% of one-stop connections
    • Atlanta Hartsfield-Jackson (ATL) - 38% of one-stop connections
    • Charlotte Douglas (CLT) - 4% of one-stop connections
    • Newark (EWR) - 2% of one-stop connections

    Dallas/Fort Worth (DFW) 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 50% on the Portland to Key West route. Wednesday is the cheapest departure day at $464 round-trip on average, while Sunday is the most expensive at $916, a difference of $452. 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 2,685 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 $459 to $2,675. That means the highest observed fare was about 6x 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 lower than usual. Average one-way flight prices are about $363, which is 25% below 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 Dallas/Fort Worth (DFW) gives the shortest average 1-stop total travel time at 8h 38m, compared with 8h 53m via Atlanta Hartsfield-Jackson (ATL) and 10h 00m via Miami (MIA).

  • What is the time difference between Portland and Key West?

    Key West is 3 hours ahead of Portland (Eastern Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • 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 $464 to $783, with an average of $618 over the past 12 months. Anything below $464 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 Sunday. On this route, Wednesday flights average $464 - about $452 less than Sunday (49% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Portland to Key West trip for April. Fares historically average $428 round-trip in that month - typically $486 less than the most expensive month, which is October (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
    - Parrot Key Hotel & Villas
    - Fairfield Inn & Suites by Marriott Key West at The Keys Collection

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