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Cheap Flights from Portland to Key West

Explore the cheapest flights from Portland to Key West in the next three months. Based on Trip.com's data from the latest 7 days, one-way fares start at AU$ 478, and round-trip tickets start at AU$ 576.

      • PDX 06:04
        8h 9m
        1 stop
        EYW 17:13
        Portland - Key West | Tue, Jan 6 | Delta Air Lines
        EYW 14:35
        11h 4m
        1 stop
        PDX 22:39
        Key West - Portland | Wed, Jan 14 | Delta Air Lines
        AU$ 576 AU$ 1,271
        55% OFF
        55% OFF
        AU$ 1,271 AU$ 576
      • PDX 23:05
        10h 58m
        1 stop
        EYW 13:03
        Portland - Key West | Tue, Jan 6 | United Airlines
        EYW 16:15
        9h 17m
        1 stop
        PDX 22:32
        Key West - Portland | Wed, Jan 14 | United Airlines
        AU$ 651 AU$ 1,271
        49% OFF
        49% OFF
        AU$ 1,271 AU$ 651
      • PDX 23:05
        10h 58m
        1 stop
        EYW 13:03
        Portland - Key West | Thu, Jan 22 | United Airlines
        EYW 16:15
        9h 17m
        1 stop
        PDX 22:32
        Key West - Portland | Tue, Jan 27 | United Airlines
        AU$ 734 AU$ 1,271
        42% OFF
        42% OFF
        AU$ 1,271 AU$ 734
      • PDX 23:28
        11h 23m
        1 stop
        EYW 13:51
        Portland - Key West | Sun, Dec 14 | United Airlines
        EYW 13:25
        10h 23m
        1 stop
        PDX 20:48
        Key West - Portland | Sat, Dec 20 | United Airlines
        AU$ 738
        42% OFF
        AU$ 1,271 AU$ 738
      • PDX 23:21
        11h 30m
        1 stop
        EYW 13:51
        Portland - Key West | Sat, Dec 13 | United Airlines
        EYW 16:05
        9h 10m
        1 stop
        PDX 22:15
        Key West - Portland | Wed, Dec 17 | United Airlines
        AU$ 863
        32% OFF
        AU$ 1,271 AU$ 863
      • PDX 06:10
        8h 5m
        1 stop
        EYW 17:15
        Portland - Key West | Sun, Dec 14 | Delta Air Lines
        EYW 11:47
        10h 6m
        1 stop
        PDX 18:53
        Key West - Portland | Sun, Dec 21 | Delta Air Lines
        AU$ 940
        26% OFF
        AU$ 1,271 AU$ 940
      • PDX 06:10
        8h 5m
        1 stop
        EYW 17:15
        Portland - Key West | Wed, Dec 10 | Delta Air Lines
        EYW 07:40
        30h 4m
        1 stop
        PDX 10:44
        Key West - Portland | Sun, Dec 14 | Delta Air Lines
        AU$ 960
        24% OFF
        AU$ 1,271 AU$ 960
      • PDX 23:19
        11h 32m
        1 stop
        EYW 13:51
        Portland - Key West | Tue, Dec 16 | United Airlines
        EYW 16:10
        9h 30m
        1 stop
        PDX 22:40
        Key West - Portland | Sat, Dec 20 | United Airlines
        AU$ 1,029
        19% OFF
        AU$ 1,271 AU$ 1,029
      • PDX 05:30
        7h 56m
        1 stop
        EYW 16:26
        Portland - Key West | Sun, Dec 14 | American Airlines
        EYW 14:52
        11h 14m
        1 stop
        PDX 23:06
        Key West - Portland | Sat, Dec 20 | American Airlines
        AU$ 1,060
        17% OFF
        AU$ 1,271 AU$ 1,060
      • PDX 23:21
        9h 13m
        1 stop
        EYW 11:34
        Portland - Key West | Sat, Dec 20 | American Airlines
        EYW 11:47
        16h 12m
        1 stop
        PDX 00:59
        Key West - Portland | Wed, Dec 24 | American Airlines
        AU$ 1,131
        11% OFF
        AU$ 1,271 AU$ 1,131
      • PDX 13:00
        17h 25m
        1 stop
        EYW Invalid Date
        Portland - Key West | Fri, Dec 12 | Normal Airline
        EYW 15:00
        6h
        Direct
        PDX 16:00
        Key West - Portland | Sun, Dec 14 | Normal Airline
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flying from Portland to Key West

The distance between Portland and Key West is approximately 4,323.57km. 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 return ticket priceAU$ 576
Off-season for travelSeptember
Peak season for travelJuly
Flight distance4,323.57km

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
From price
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  • 714
  • 1421
  • 2128

  • Jan

    284
  • 411
  • 1118
  • 1825

  • Feb

    251
  • 18
  • 815
  • 1522

  • Mar

    221
Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • Which airlines offer the cheapest flights from Portland (PDX) to Key West (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 cancelled 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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