$250 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 1/28. 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

Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m1 stop
Multiple Airlines Logo
11:30 am - 8:44 pm
GCM
-
PDX
12h 14m1 stop
$528Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m1 stop
Multiple Airlines Logo
11:30 am - 11:44 pm
GCM
-
PDX
15h 14m2 stops
$601Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Air Canada Logo
7:05 pm - 12:25 pm
PDX
-
GCM
38h 20m2 stops
Air Canada Logo
1:30 pm - 2:40 pm
GCM
-
PDX
28h 10m2 stops
$623Air Canada
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
9:50 am - 12:25 pm
PDX
-
GCM
23h 35m2 stops
Multiple Airlines Logo
5:10 pm - 8:33 pm
GCM
-
PDX
30h 23m1 stop
$640Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m2 stops
$653Air Canada
Wed, Feb 18 - Wed, Feb 25
Multiple Airlines Logo
7:05 am - 2:00 pm
PDX
-
GCM
27h 55m1 stop
Multiple Airlines Logo
5:10 pm - 8:33 pm
GCM
-
PDX
30h 23m1 stop
$657Multiple Airlines
Wed, Feb 11 - Mon, Feb 16
American Airlines Logo
11:07 pm - 2:45 pm
PDX
-
GCM
12h 38m1 stop
American Airlines Logo
8:45 am - 11:50 pm
GCM
-
PDX
18h 05m1 stop
$667American Airlines
Tue, Feb 10 - Sun, Feb 15
American Airlines Logo
11:01 pm - 8:20 pm
PDX
-
GCM
18h 19m1 stop
American Airlines Logo
8:45 am - 11:50 pm
GCM
-
PDX
18h 05m1 stop
$672American Airlines
Tue, Feb 10 - Sun, Feb 15
American Airlines Logo
5:25 am - 8:20 pm
PDX
-
GCM
11h 55m2 stops
American Airlines Logo
3:35 pm - 12:17 am
GCM
-
PDX
11h 42m1 stop
$677American Airlines
Thu, Mar 19 - Thu, Mar 26
American Airlines Logo
1:52 pm - 2:25 pm
PDX
-
GCM
22h 33m1 stop
American Airlines Logo
3:30 pm - 11:09 pm
GCM
-
PDX
9h 39m1 stop
$682American 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 February, when the average cost of round-trip tickets is $1,179 and $932 respectively.

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Good to know

Low seasonJanuary
Cheapest flight$250
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 7% 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 11111 reviews
6.9Entertainment
7.2Comfort
7.5Boarding
6.4Food
8.0Crew
Airline reviews

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

8.0 ExcellentDavid, Jan 2026
CHA - DFW
Read more American Airlines reviews

The flight was good. We had to spend almost an hour on the tarmac when we arrived in Dallas. Waiting for a gate. What’s the point of arriving early if you have no gate to park at?

Lower WiFi prices; allow us to see our flight on a map; more variety of drink choices.

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

Seats were much more cramped then on the 737. Narrower and rows closer together. Flight was absolutely packed and the plugs under the seats didn't work. Was forced to check my bag even though previous flight had no issue with it.

Good food & refreshment. The seats and entrainment screens are modern compared to others. The staff though pleasant serve and attend to passengers based on nationality. Some get served first others last regardless of their seating positions.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

The flight was on time and arrived early. The crew were friendly and helpful.

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

Information on your arrival and departure airports

Portland (PDX)