$264 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 6/1. 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 - Thu, May 7
Southwest Logo
2:45 pm - 12:10 pm
PDX
-
GCM
19h 25m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$594Southwest
Sun, May 3 - Thu, May 7
Southwest Logo
2:45 pm - 12:10 pm
PDX
-
GCM
19h 25m
2 stops
Southwest Logo
1:05 pm - 12:25 am
GCM
-
PDX
13h 20m
2 stops
$626Southwest
Thu, Apr 23 - Wed, Apr 29
Southwest Logo
2:50 pm - 12:10 pm
PDX
-
GCM
19h 20m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$633Southwest
Wed, Apr 29 - Wed, May 6
Southwest Logo
7:25 pm - 12:10 pm
PDX
-
GCM
14h 45m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$683Southwest
Sun, May 10 - Sun, May 17
Southwest Logo
2:45 pm - 12:10 pm
PDX
-
GCM
19h 25m
2 stops
Southwest Logo
12:50 pm - 1:25 am
GCM
-
PDX
14h 35m
2 stops
$713Southwest
Tue, May 5 - Sat, May 9
Air Canada Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Air Canada Logo
10:55 am - 9:30 am
GCM
-
PDX
24h 35m
2 stops
$716Air Canada
Tue, May 26 - Sun, May 31
Southwest Logo
1:35 pm - 12:10 pm
PDX
-
GCM
20h 35m
2 stops
Southwest Logo
12:50 pm - 1:15 am
GCM
-
PDX
14h 25m
2 stops
$727Southwest
Fri, May 1 - Thu, May 7
Multiple Airlines Logo
11:48 am - 7:10 pm
PDX
-
GCM
29h 22m
1 stop
Multiple Airlines Logo
12:40 pm - 4:46 pm
GCM
-
PDX
30h 06m
2 stops
$745Multiple Airlines
Thu, Apr 23 - Wed, Apr 29
American Airlines Logo
10:28 pm - 11:00 am
PDX
-
GCM
10h 32m
1 stop
American Airlines Logo
12:00 pm - 10:49 pm
GCM
-
PDX
12h 49m
2 stops
$767American Airlines
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
5:51 pm - 6:00 pm
PDX
-
GCM
22h 09m
2 stops
Multiple Airlines Logo
8:00 am - 8:45 pm
GCM
-
PDX
14h 45m
1 stop
$776Multiple 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 $1,211 and $991 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$264
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 49% 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.
7.1
American AirlinesOverall score based on 11550 reviews
8.0Crew
7.2Comfort
6.9Entertainment
7.5Boarding
6.4Food
Airline reviews

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

2.0 MediocreIan, Apr 2026
ORD - DFW
Read more American Airlines reviews

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Flight was delayed. No urgency by American Airlines team to assist those with connecting flights. It was basically you are on your own to run through the terminals to try and make your connection. Thanks, Mary

I have never been assaulted they way I was today in Charlotte - shame on American

One of our group members was struggling to walk. In Charlotte we asked for a wheelchair and she was accompanied by Desmond. I was impressed by his patience and attention. In Boston she received the same service. I didn’t get the name of the helper but she went above and beyond in assisting us. A great AA service

Better snacks but flight and crew were amazing on this flight

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

It was the most un-special flight experience in my life.

Plane was super cold. No entertainment unless you were with mileage program Getting off the plane was super slow

Flight was on-time, boarding was flawless and the crew was friendly.

The staff are very, very professional. It's what flying should feel like.

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

Information on your arrival and departure airports

Portland (PDX)