$193 Find Cheap Flights from Portland to the Cayman Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Portland to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
George Town
George Town
9h 45m2 stops
from $599per person
Booking Insights

Price, demand and travel trends for Portland to the Cayman Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Portland to the Cayman Islands right now?

The cheapest fare from Portland to the Cayman Islands in the last week was $599 round-trip, to George Town Owen Roberts Intl (GCM).

Which airport in the Cayman Islands is the cheapest to fly to from Portland?

All flights from Portland to the Cayman Islands arrive at George Town Owen Roberts Intl (GCM). On average, round-trip fares are around $781.

What’s the cheapest day to fly from Portland to the Cayman Islands?

Wednesday tends to be the cheapest day to fly from Portland to the Cayman Islands, while Saturday is the most expensive. Fares run about 60% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Portland to the Cayman Islands?

Data from the past 12 months shows it's cheapest to fly to the Cayman Islands during the evening with average prices of $681. The morning is the most expensive time to fly, with average prices of $1,676.

Key details for Portland to the Cayman Islands flights

Low season

September

Cheapest flight

$193
One-way flight from Portland to George Town

Your Portland to the Cayman Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to the Cayman Islands?

    Yes. Fares from Portland to the Cayman Islands are low right now. As a rule of thumb, a round-trip under $709 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Portland to the Cayman Islands?

    Over the past 12 months, round-trip fares from Portland to the Cayman Islands have ranged from $709 to $974.

  • What are the main airports serving the Cayman Islands?

    Flights to the Cayman Islands all arrive at George Town Owen Roberts Intl (GCM).

  • What airlines fly nonstop from Portland to the Cayman Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to the Cayman Islands. One-stop options include:

    • American Airlines
    • Delta
    • United Airlines

  • Which cabin classes are available on flights from Portland to the Cayman Islands?

    On flights from Portland to the Cayman Islands you can only book Economy Class.

Your guide to booking Portland to the Cayman Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for December when flights are typically cheapest and avoid March when prices are at their highest.
  • Flying on Wednesday is usually the cheapest. Flights on Saturday cost about 60% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in George Town, which is the most popular destination in the Cayman Islands. From there, it's easy to continue on to other popular destinations such as West Bay, East End and North Side.

Reviews of the top airline flying from Portland to the Cayman Islands

 
Need help choosing which airline to fly with from Portland to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
American AirlinesOverall score based on 12129 reviews
7.9Crew
6.4Food
7.4Boarding
6.8Entertainment
7.2Comfort
Airline reviews

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

10.0 ExcellentJulian, Jul 2026
Read more American Airlines reviews

Luggage took too long go get off plane in Knoxville. Was almost 45 minutes after the flight landed.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

As smooth as you can expect. Some issues with boarding because the previous plane took forever to deplane but overall, a good experience.

DFW-LHR Toilets not kept clean Too cramped. Aisles so narrow crew were constantly banging into people on the aisle seats. Even then, the carts used are reduced width. Other than that it was a decent flight on both legs

Excellent customer service at check in at Austin flight to DFW and excellent customer service from Karren in terminal B at DFW.

The flight itself was fine, but between the man in front of me putting his chair back, and the gentleman next to me who took up 50% of my seat, my back and neck are destroyed from the flight. I’m hoping for a better outcome flying back.

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

We were told there would be no food/beverage service due to turbulence. There was very little turbulence on the 2+ hour flight. I was in First Class and thought they could have done a quick service after take off as they had a quite bit of time before we would be reaching the predicted turbulent area. They could have at least passed out a quick bag of pretzels.

Very disappointed with the crew and the lack of attention given to the passengers. On a 5 hour flight they never offered a snack. One time offered a beverage and didn’t pick up the used cups until the flight was on final approach. The two flight attendants in our section mentioned that they were best friends and compared their pre flight shoes. When paying for first/business class there is a level of service that should be expected. These two spent the majority of the flight in their seats playing on their phones and laughing with each other. Very frustrating!!!

More options for your flight from Portland to the Cayman Islands

Complete your trip to the Cayman Islands with a hotel stay or car rental