$675 Find Cheap Flights from Portland to the Cayman Islands - Compare and Save

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to the Cayman Islands departing on 12/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Book Cheap Portland to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to the Cayman Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to the Cayman Islands

Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
7:18 am - 9:15 pm
PDX
-
GCM
10h 57m
1 stop
Multiple Airlines Logo
7:00 am - 8:50 pm
GCM
-
PDX
16h 50m
1 stop
$675Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
10:00 am - 12:10 pm
PDX
-
GCM
23h 10m
2 stops
Multiple Airlines Logo
4:45 pm - 8:50 pm
GCM
-
PDX
31h 05m
1 stop
$695Multiple Airlines
Wed, Aug 19 - Sat, Aug 29
Multiple Airlines Logo
6:20 am - 11:35 am
PDX
-
GCM
27h 15m
2 stops
Multiple Airlines Logo
4:00 pm - 11:35 am
GCM
-
PDX
21h 35m
1 stop
$722Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
5:00 am - 9:15 pm
PDX
-
GCM
13h 15m
2 stops
Multiple Airlines Logo
1:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$759Multiple Airlines
Thu, Oct 8 - Sat, Oct 17
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 7:06 pm
GCM
-
PDX
32h 41m
2 stops
$775Air Canada
Wed, Aug 19 - Sat, Aug 29
American Airlines Logo
10:59 pm - 11:27 am
PDX
-
GCM
10h 28m
1 stop
American Airlines Logo
3:17 pm - 11:09 pm
GCM
-
PDX
9h 52m
1 stop
$786American Airlines
Wed, Aug 19 - Sat, Aug 29
American Airlines Logo
11:34 pm - 1:10 pm
PDX
-
GCM
11h 36m
2 stops
American Airlines Logo
4:00 pm - 10:54 am
GCM
-
PDX
20h 54m
2 stops
$791American Airlines
Sat, Aug 8 - Thu, Aug 13
Multiple Airlines Logo
5:39 pm - 3:45 pm
PDX
-
GCM
20h 06m
1 stop
Multiple Airlines Logo
4:45 pm - 4:54 pm
GCM
-
PDX
26h 09m
2 stops
$852Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
10:00 am - 12:10 pm
PDX
-
GCM
23h 10m
2 stops
Multiple Airlines Logo
2:50 pm - 2:41 pm
GCM
-
PDX
26h 51m
3 stops
$865Multiple Airlines
Thu, Oct 8 - Sat, Oct 17
Delta Logo
2:30 pm - 11:40 am
PDX
-
GCM
19h 10m
1 stop
Delta Logo
12:55 pm - 10:26 pm
GCM
-
PDX
11h 31m
1 stop
$881Delta
Booking Insights

KAYAK's insights & trends for Portland to the Cayman Islands flights

Get data-powered insights and trends into flights from Portland to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Portland to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to the Cayman Islands is December, when tickets cost $665 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $948 and $781 respectively.

Good to know

Low seasonJanuary
Cheapest flight$675
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Portland to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Portland to the Cayman Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to the Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to the Cayman Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to the Cayman Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Portland to the Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to the Cayman Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Portland to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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.
7.1
American AirlinesOverall score based on 11768 reviews
7.9Crew
7.5Boarding
6.4Food
7.2Comfort
6.8Entertainment
Airline reviews

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.

2.0 MediocreMatthew, May 2026
PDX - ORD
Read more American Airlines reviews

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!!!

I love the Kayak has keep on updating me about flight status as it was delayed for 30mins. as well notifications to book seat and if any change on booking. Tickets were also cheap compared to British Airways online website. No hidden charges or terms n conditions. Keep it up!!!

Everything you need to know for your flight from Portland to the Cayman Islands

Information on your arrival and departure airports