$314 Find Cheap Flights from Portland to the Cayman Islands

This is the cheapest one-way 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 2/14. 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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Flight Deals

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, May 3 - Fri, May 8
Southwest Logo
4:25 pm - 12:10 pm
PDX
-
GCM
17h 45m
2 stops
Southwest Logo
1:05 pm - 10:40 pm
GCM
-
PDX
11h 35m
2 stops
$517Southwest
Sun, May 17 - Mon, May 25
Air Canada Logo
3:25 pm - 11:30 am
PDX
-
GCM
18h 05m
2 stops
Air Canada Logo
12:25 pm - 2:45 pm
GCM
-
PDX
28h 20m
2 stops
$565Air Canada
Sat, May 2 - Fri, May 8
Southwest Logo
2:40 pm - 11:55 am
PDX
-
GCM
19h 15m
2 stops
Southwest Logo
1:05 pm - 10:40 pm
GCM
-
PDX
11h 35m
2 stops
$567Southwest
Mon, Mar 2 - Mon, Mar 9
Southwest Logo
3:40 pm - 12:55 pm
PDX
-
GCM
18h 15m
2 stops
Southwest Logo
12:40 pm - 12:45 am
GCM
-
PDX
14h 05m
2 stops
$582Southwest
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
6:00 am - 9:15 pm
PDX
-
GCM
12h 15m
2 stops
Multiple Airlines Logo
4:45 pm - 8:44 pm
GCM
-
PDX
29h 59m
1 stop
$590Multiple Airlines
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
11h 15m
1 stop
Multiple Airlines Logo
4:45 pm - 8:44 pm
GCM
-
PDX
29h 59m
1 stop
$591Multiple Airlines
Sun, May 17 - Mon, May 25
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
13h 45m
2 stops
Air Canada Logo
12:25 pm - 9:30 am
GCM
-
PDX
23h 05m
2 stops
$624Air Canada
Sun, Apr 26 - Sat, May 2
Multiple Airlines Logo
6:00 am - 11:35 am
PDX
-
GCM
27h 35m
2 stops
Multiple Airlines Logo
4:00 pm - 11:57 am
GCM
-
PDX
21h 57m
1 stop
$665Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m
2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m
2 stops
$685Air Canada
Sun, May 3 - Fri, May 8
United Airlines Logo
7:05 pm - 12:30 pm
PDX
-
GCM
15h 25m
2 stops
United Airlines Logo
1:35 pm - 10:59 pm
GCM
-
PDX
11h 24m
1 stop
$687United Airlines
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 January, when tickets cost $666 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $1,179 and $915 respectively.

Good to know

Low seasonJanuary
Cheapest flight$314
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 6% 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.
7.2
American AirlinesOverall score based on 11216 reviews
8.0Crew
6.9Entertainment
7.2Comfort
6.4Food
7.5Boarding
Airline reviews

The screens were inoperable for movies and such, but everything else was just fine

10.0 ExcellentBenn, Feb 2026
HNL - DFW
Read more American Airlines reviews

The screens were inoperable for movies and such, but everything else was just fine

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

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

Information on your arrival and departure airports