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Flights from Portland to Key West

Find flight deals from Portland to Key West for the next 3 months. Book one way flights from AU$478 or round trip flights from AU$576.

      • PDX 6:04 AM
        8h 9m
        1 stop
        EYW 5:13 PM
        Portland - Key West | Tue, Jan 6 | Delta Air Lines
        EYW 2:35 PM
        11h 4m
        1 stop
        PDX 10:39 PM
        Key West - Portland | Wed, Jan 14 | Delta Air Lines
        AU$576 AU$1,615
        64% OFF
        64% OFF
        AU$1,615 AU$576
      • PDX 11:05 PM
        10h 58m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Tue, Jan 6 | United Airlines
        EYW 4:15 PM
        9h 17m
        1 stop
        PDX 10:32 PM
        Key West - Portland | Wed, Jan 14 | United Airlines
        AU$651 AU$1,615
        60% OFF
        60% OFF
        AU$1,615 AU$651
      • PDX 11:05 PM
        10h 58m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Thu, Jan 22 | United Airlines
        EYW 4:15 PM
        9h 17m
        1 stop
        PDX 10:32 PM
        Key West - Portland | Tue, Jan 27 | United Airlines
        AU$734 AU$1,615
        55% OFF
        55% OFF
        AU$1,615 AU$734
      • PDX 11:28 PM
        11h 23m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Sun, Dec 14 | United Airlines
        EYW 1:25 PM
        10h 23m
        1 stop
        PDX 8:48 PM
        Key West - Portland | Sat, Dec 20 | United Airlines
        AU$738
        54% OFF
        AU$1,615 AU$738
      • PDX 11:21 PM
        11h 30m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Sat, Dec 13 | United Airlines
        EYW 4:05 PM
        9h 10m
        1 stop
        PDX 10:15 PM
        Key West - Portland | Wed, Dec 17 | United Airlines
        AU$863
        47% OFF
        AU$1,615 AU$863
      • PDX 6:10 AM
        8h 5m
        1 stop
        EYW 5:15 PM
        Portland - Key West | Sun, Dec 14 | Delta Air Lines
        EYW 11:47 AM
        10h 6m
        1 stop
        PDX 6:53 PM
        Key West - Portland | Sun, Dec 21 | Delta Air Lines
        AU$940
        42% OFF
        AU$1,615 AU$940
      • PDX 6:10 AM
        8h 5m
        1 stop
        EYW 5:15 PM
        Portland - Key West | Wed, Dec 10 | Delta Air Lines
        EYW 7:40 AM
        30h 4m
        1 stop
        PDX 10:44 AM
        Key West - Portland | Sun, Dec 14 | Delta Air Lines
        AU$960
        41% OFF
        AU$1,615 AU$960
      • PDX 11:19 PM
        11h 32m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Tue, Dec 16 | United Airlines
        EYW 4:10 PM
        9h 30m
        1 stop
        PDX 10:40 PM
        Key West - Portland | Sat, Dec 20 | United Airlines
        AU$1,028
        36% OFF
        AU$1,615 AU$1,028
      • PDX 5:30 AM
        7h 56m
        1 stop
        EYW 4:26 PM
        Portland - Key West | Sun, Dec 14 | American Airlines
        EYW 2:52 PM
        11h 14m
        1 stop
        PDX 11:06 PM
        Key West - Portland | Sat, Dec 20 | American Airlines
        AU$1,060
        34% OFF
        AU$1,615 AU$1,060
      • PDX 11:21 PM
        9h 13m
        1 stop
        EYW 11:34 AM
        Portland - Key West | Sat, Dec 20 | American Airlines
        EYW 11:47 AM
        16h 12m
        1 stop
        PDX 12:59 AM
        Key West - Portland | Wed, Dec 24 | American Airlines
        AU$1,131
        30% OFF
        AU$1,615 AU$1,131
      • PDX 1:00 PM
        17h 25m
        1 stop
        EYW Invalid Date
        Portland - Key West | Thu, Dec 11 | Normal Airline
        EYW 3:00 PM
        6h
        Nonstop
        PDX 4:00 PM
        Key West - Portland | Sat, Dec 13 | Normal Airline
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Displayed flight fares from Portland to Key West are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flying from Portland to Key West

The distance between Portland and Key West is approximately 4,323.57 km. Based on Trip.com's data travel demand peaks in July. The off-season for travel is September.

Cheapest one-way flight priceAU$478
Cheapest round-trip ticket priceAU$576
Off-season for travelSeptember
Peak season for travelJuly
Flight distance4,323.57 km

When is the cheapest time to fly from Portland to Key West?

The cheapest time for Portland to Key West flights: Dec 21 to Dec 28 — one way flight prices from AU$266.

Cheapest flights
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  • 714
  • 1421
  • 2128

  • Jan

    284
  • 411
  • 1118
  • 1825

  • Feb

    251
  • 18
  • 815
  • 1522

  • Mar

    221
Displayed fare trends are based on Trip.com's aggregated average of the lowest flight prices from Portland to Key West, calculated over the upcoming 10 weeks.

Frequently Asked Questions

  • What are the cheapest flights from Portland to Key West (PDX-EYW)?

    Based on Trip.com data, American Airlines offers one-way fares as low as AU$478 on Cheapest nonstop routes (e.g. PDX to EYW on Wed, Dec 31), while Delta Air Lines offers Cheapest nonstop round-trips from AU$576 departing on Tue, Jan 6 and returning on Wed, Jan 14.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Portland to Key West is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • To find best deals on flights from Portland to Key West, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Wed, Dec 31, with one-way flights priced at just AU$478.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Key West travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Portland to Key West is September, when demand for travel is lower.
  • After crunching the numbers on our December flight calendar, it's currently cheapest to fly from Portland to Key West on December 14, 2025 with United Airlines, with prices starting at AU$737.
  • The time difference between Key West and Portland is 3h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

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