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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 SGD 236 or round trip flights from SGD 394.

      • PWM 6:00 AM
        6h 48m
        1 stop
        EYW 12:48 PM
        Portland - Key West | Wed, Jan 7 | Delta Air Lines
        EYW 2:45 PM
        7h 42m
        1 stop
        PWM 10:27 PM
        Key West - Portland | Wed, Jan 14 | Delta Air Lines
        SGD 394 SGD 741
        47% OFF
        47% OFF
        SGD 741 SGD 394
      • PWM 6:00 AM
        7h 51m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Tue, Dec 16 | United Airlines
        EYW 5:10 PM
        6h 49m
        1 stop
        PWM 11:59 PM
        Key West - Portland | Sun, Dec 21 | United Airlines
        SGD 440 SGD 741
        41% OFF
        41% OFF
        SGD 741 SGD 440
      • PWM 6:00 AM
        7h 3m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Wed, Jan 7 | United Airlines
        EYW 2:25 PM
        18h 36m
        1 stop
        PWM 9:01 AM
        Key West - Portland | Wed, Jan 14 | United Airlines
        SGD 545 SGD 741
        26% OFF
        26% OFF
        SGD 741 SGD 545
      • PWM 6:00 AM
        7h 51m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Sun, Dec 14 | United Airlines
        EYW 3:09 PM
        8h 13m
        1 stop
        PWM 11:22 PM
        Key West - Portland | Thu, Dec 18 | United Airlines
        SGD 571
        23% OFF
        SGD 741 SGD 571
      • PWM 6:00 AM
        8h 13m
        1 stop
        EYW 2:13 PM
        Portland - Key West | Sun, Dec 21 | United Airlines
        EYW 3:09 PM
        8h 13m
        1 stop
        PWM 11:22 PM
        Key West - Portland | Thu, Dec 25 | United Airlines
        SGD 576
        22% OFF
        SGD 741 SGD 576
      • PWM 6:08 AM
        7h 59m
        1 stop
        EYW 2:07 PM
        Portland - Key West | Tue, Dec 16 | Delta Air Lines
        EYW 4:25 PM
        6h 18m
        1 stop
        PWM 10:43 PM
        Key West - Portland | Sun, Dec 21 | Delta Air Lines
        SGD 584
        21% OFF
        SGD 741 SGD 584
      • PWM 5:30 AM
        5h 59m
        1 stop
        EYW 11:29 AM
        Portland - Key West | Sun, Jan 11 | Delta Air Lines
        EYW 1:28 PM
        21h 52m
        1 stop
        PWM 11:20 AM
        Key West - Portland | Sun, Jan 18 | Delta Air Lines
        SGD 612
        18% OFF
        SGD 741 SGD 612
      • PWM 6:00 AM
        7h 51m
        1 stop
        EYW 1:51 PM
        Portland - Key West | Fri, Dec 12 | United Airlines
        EYW 2:47 PM
        8h 22m
        1 stop
        PWM 11:09 PM
        Key West - Portland | Tue, Dec 16 | United Airlines
        SGD 629
        15% OFF
        SGD 741 SGD 629
      • PWM 6:00 AM
        8h 13m
        1 stop
        EYW 2:13 PM
        Portland - Key West | Thu, Dec 18 | United Airlines
        EYW 3:09 PM
        8h 13m
        1 stop
        PWM 11:22 PM
        Key West - Portland | Mon, Dec 22 | United Airlines
        SGD 664
        10% OFF
        SGD 741 SGD 664
      • PWM 6:00 AM
        8h 13m
        1 stop
        EYW 2:13 PM
        Portland - Key West | Tue, Dec 23 | United Airlines
        EYW 5:43 PM
        5h 39m
        1 stop
        PWM 11:22 PM
        Key West - Portland | Sat, Dec 27 | United Airlines
        SGD 667
        10% OFF
        SGD 741 SGD 667
      • PWM 1:00 PM
        17h 25m
        1 stop
        EYW Invalid Date
        Portland - Key West | Sat, Dec 13 | Normal Airline
        EYW 3:00 PM
        6h
        Nonstop
        PWM 4:00 PM
        Key West - Portland | Mon, Dec 15 | Normal Airline
        Find More Flights
        Find More Flights
      • PWM 5:30 AM
        8h 18m
        1 stop
        EYW 1:48 PM
        Portland - Key West | Wed, Jan 14 | Delta Air Lines
        SGD 236 SGD 388
        39% OFF
        39% OFF
        SGD 388 SGD 236
      • PWM 6:03 AM
        8h 4m
        1 stop
        EYW 2:07 PM
        Portland - Key West | Sun, Dec 14 | Delta Air Lines
        SGD 238 SGD 388
        39% OFF
        39% OFF
        SGD 388 SGD 238
      • PWM 5:30 AM
        6h 1m
        1 stop
        EYW 11:31 AM
        Portland - Key West | Fri, Jan 9 | Delta Air Lines
        SGD 281 SGD 388
        28% OFF
        28% OFF
        SGD 388 SGD 281
      • PWM 6:00 AM
        6h 48m
        1 stop
        EYW 12:48 PM
        Portland - Key West | Tue, Jan 20 | Delta Air Lines
        SGD 281
        28% OFF
        SGD 388 SGD 281
      • PWM 6:00 AM
        8h 6m
        1 stop
        EYW 2:06 PM
        Portland - Key West | Sun, Dec 14 | United Airlines
        SGD 282
        27% OFF
        SGD 388 SGD 282
      • PWM 6:00 AM
        7h 3m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Tue, Jan 20 | United Airlines
        SGD 283
        27% OFF
        SGD 388 SGD 283
      • PWM 6:00 AM
        8h 13m
        1 stop
        EYW 2:13 PM
        Portland - Key West | Fri, Jan 2 | United Airlines
        SGD 284
        27% OFF
        SGD 388 SGD 284
      • PWM 6:00 AM
        7h 3m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Wed, Jan 14 | United Airlines
        SGD 331
        15% OFF
        SGD 388 SGD 331
      • PWM 6:00 AM
        7h 3m
        1 stop
        EYW 1:03 PM
        Portland - Key West | Sat, Jan 24 | United Airlines
        SGD 331
        15% OFF
        SGD 388 SGD 331
      • PWM 7:00 AM
        6h 37m
        1 stop
        EYW 1:37 PM
        Portland - Key West | Fri, Jan 2 | Delta Air Lines
        SGD 349
        10% OFF
        SGD 388 SGD 349
      • PWM 1:00 PM
        17h 25m
        1 stop
        EYW Invalid Date
        Portland - Key West | Sat, Dec 13 | Normal Airline
        Find More Flights
        Find More Flights

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.

Flight Info | Portland to Key West

The distance between Portland and Key West is approximately 2,365.58 km. Based on Trip.com's data travel demand peaks in December. The off-season for travel is November.

Cheapest one-way flight priceSGD 236
Cheapest round-trip ticket priceSGD 394
Off-season for travelNovember
Peak season for travelDecember
Flight distance2,365.58 km

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

The cheapest time for Portland to Key West flights: Jan 11 to Jan 18 — one way flight prices from SGD 235.

Cheapest flights
From price
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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 (PWM-EYW)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as SGD 236 on Cheapest nonstop routes (e.g. PWM to EYW on Wed, Jan 14), while Delta Air Lines offers Cheapest nonstop round-trips from SGD 394 departing on Wed, Jan 7 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, Jan 14, with one-way flights priced at just SGD 236.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Delta Air Lines.
    · 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 December.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Portland to Key West is November, 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 16, 2025 with United Airlines, with prices starting at SGD 439.
  • The time difference between Key West and Portland is 0h.
  • 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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