$525 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 10/18. 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, Oct 18 - Sun, Oct 25
Air Canada Logo
10:10 am - 11:30 am
PDX
-
GCM
23h 20m
2 stops
Air Canada Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$525Air Canada
Sat, Oct 17 - Sun, Oct 25
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$614Air Canada
Tue, Jul 7 - Tue, Jul 21
Southwest Logo
9:20 pm - 11:55 am
PDX
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 11:35 pm
GCM
-
PDX
12h 45m
2 stops
$682Southwest
Mon, Oct 19 - Sun, Oct 25
Multiple Airlines Logo
6:06 am - 9:15 pm
PDX
-
GCM
13h 09m
2 stops
Multiple Airlines Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$684Multiple Airlines
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
9:20 pm - 11:55 am
PDX
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 11:35 pm
GCM
-
PDX
12h 45m
2 stops
$727Southwest
Sun, Oct 18 - Sun, Oct 25
Multiple Airlines Logo
9:30 pm - 2:45 pm
PDX
-
GCM
15h 15m
1 stop
Multiple Airlines Logo
12:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$731Multiple Airlines
Wed, Oct 7 - Sun, Oct 11
Multiple Airlines Logo
6:06 am - 11:35 am
PDX
-
GCM
27h 29m
2 stops
Multiple Airlines Logo
6:10 pm - 9:32 am
GCM
-
PDX
17h 22m
1 stop
$740Multiple Airlines
Mon, Jun 29 - Mon, Jul 6
Southwest Logo
6:00 pm - 11:55 am
PDX
-
GCM
15h 55m
2 stops
Southwest Logo
12:50 pm - 11:55 pm
GCM
-
PDX
13h 05m
2 stops
$757Southwest
Sat, Oct 17 - Sun, Oct 25
Multiple Airlines Logo
6:00 pm - 4:00 pm
PDX
-
GCM
20h 00m
1 stop
Multiple Airlines Logo
12:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$761Multiple Airlines
Mon, Jun 29 - Mon, Jul 6
American Airlines Logo
11:43 pm - 1:35 pm
PDX
-
GCM
11h 52m
1 stop
American Airlines Logo
2:41 pm - 10:51 pm
GCM
-
PDX
10h 10m
1 stop
$781American 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 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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$525
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 8% 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 11641 reviews
6.4Food
7.5Boarding
7.9Crew
7.2Comfort
6.9Entertainment
Airline reviews

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

4.0 OkayAnonymous, Jun 2026
ORD - CDG
Read more American Airlines reviews

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

The flight from LA to Chicago was smooth and service was very good overall.

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

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

Information on your arrival and departure airports

Portland (PDX)