$547 Find Cheap Flights from Portland to the Cayman Islands

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 3/9. 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

Mon, Mar 9 - Mon, Mar 16
Southwest Logo
6:40 pm - 11:45 am
PDX
-
GCM
15h 05m
2 stops
Southwest Logo
12:40 pm - 12:45 am
GCM
-
PDX
14h 05m
2 stops
$547Southwest
Wed, Apr 8 - Thu, Apr 16
Air Canada Logo
7:05 pm - 10:10 am
PDX
-
GCM
37h 05m
2 stops
Air Canada Logo
11:55 am - 6:30 pm
GCM
-
PDX
32h 35m
2 stops
$554Air Canada
Mon, Apr 6 - Thu, Apr 16
Southwest Logo
2:50 pm - 12:10 pm
PDX
-
GCM
19h 20m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$562Southwest
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
12h 15m
1 stop
Multiple Airlines Logo
4:45 pm - 8:44 pm
GCM
-
PDX
29h 59m
1 stop
$573Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
7:05 pm - 11:25 am
PDX
-
GCM
14h 20m
2 stops
Multiple Airlines Logo
4:45 pm - 8:44 pm
GCM
-
PDX
29h 59m
1 stop
$591Multiple Airlines
Sun, Mar 1 - Thu, Mar 12
Air Canada Logo
7:05 pm - 12:25 pm
PDX
-
GCM
38h 20m
2 stops
Air Canada Logo
12:30 pm - 9:15 am
GCM
-
PDX
46h 45m
2 stops
$630Air Canada
Mon, Mar 2 - Sun, Mar 8
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
11h 15m
1 stop
Multiple Airlines Logo
1:49 pm - 3:48 pm
GCM
-
PDX
27h 59m
2 stops
$645Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
7:05 pm - 11:25 am
PDX
-
GCM
14h 20m
2 stops
Multiple Airlines Logo
1:50 pm - 9:15 am
GCM
-
PDX
21h 25m
3 stops
$648Multiple Airlines
Wed, Apr 8 - Thu, Apr 16
Multiple Airlines Logo
7:05 pm - 10:10 am
PDX
-
GCM
37h 05m
2 stops
Multiple Airlines Logo
4:25 pm - 6:30 pm
GCM
-
PDX
28h 05m
3 stops
$661Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
3:15 pm - 3:25 pm
PDX
-
GCM
22h 10m
3 stops
Multiple Airlines Logo
1:50 pm - 9:15 am
GCM
-
PDX
21h 25m
3 stops
$672Multiple 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 $1,161 and $915 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$547
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 41% increase in price.
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 11297 reviews
7.5Boarding
8.0Crew
6.9Entertainment
7.2Comfort
6.4Food
Airline reviews

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

2.0 MediocreJohn, Feb 2026
ORD - STL
Read more American Airlines reviews

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

The flight was on time/early, attentive crew, and everything overall went smoothly. Disappointed that WIFI was not working for the flight.

One day, I do so hope for a gluten free snack! Seems like with the rest of the world FINALLY figuring out what gluten free is, American Airlines would too. Fingers crossed!!

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

Information on your arrival and departure airports

Portland (PDX)