$281 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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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

Sat, Dec 13 - Sun, Dec 21
Southwest Logo
4:35 pm - 12:35 pmPDX-GCM
17h 00m2 stops
Southwest Logo
1:30 pm - 12:30 amGCM-PDX
14h 00m2 stops
$661Southwest
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Sat, Dec 13 - Sun, Dec 21
United Airlines Logo
4:02 pm - 1:15 pmPDX-GCM
18h 13m2 stops
United Airlines Logo
2:50 pm - 10:40 pmGCM-PDX
10h 50m1 stop
$666United Airlines
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Sat, Jan 3 - Sat, Jan 10
Delta Logo
5:25 pm - 12:36 pmPDX-GCM
16h 11m2 stops
Delta Logo
12:15 pm - 8:59 pmGCM-PDX
11h 44m2 stops
$671Delta
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Mon, Dec 22 - Tue, Dec 30
United Airlines Logo
11:55 pm - 1:45 pmPDX-GCM
10h 50m1 stop
United Airlines Logo
5:45 pm - 1:20 pmGCM-PDX
22h 35m1 stop
$683United Airlines
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Thu, Mar 5 - Sat, Mar 14
American Airlines Logo
11:59 pm - 2:45 pmPDX-GCM
11h 46m2 stops
American Airlines Logo
8:30 am - 8:24 pmGCM-PDX
13h 54m2 stops
$710American Airlines
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Sat, Dec 13 - Sun, Dec 21
Multiple Airlines Logo
7:00 pm - 1:44 pmPDX-GCM
15h 44m2 stops
Multiple Airlines Logo
2:40 pm - 5:14 pmGCM-PDX
29h 34m3 stops
$742Multiple Airlines
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Sat, Jan 3 - Sun, Jan 11
American Airlines Logo
12:49 am - 3:25 pmPDX-GCM
11h 36m1 stop
American Airlines Logo
8:50 am - 10:38 pmGCM-PDX
16h 48m2 stops
$761American Airlines
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Mon, Dec 22 - Tue, Dec 30
United Airlines Logo
7:45 pm - 1:45 pmPDX-GCM
15h 00m2 stops
United Airlines Logo
5:45 pm - 10:01 amGCM-PDX
19h 16m2 stops
$764United Airlines
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Sun, Dec 21 - Tue, Dec 30
American Airlines Logo
12:49 am - 3:25 pmPDX-GCM
11h 36m1 stop
American Airlines Logo
1:05 pm - 12:59 amGCM-PDX
14h 54m1 stop
$828American Airlines
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Fri, Jan 2 - Sat, Jan 10
American Airlines Logo
12:49 am - 2:49 pmPDX-GCM
11h 00m2 stops
American Airlines Logo
12:16 pm - 10:11 pmGCM-PDX
12h 55m2 stops
$866American Airlines
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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 $596 (return) on average. On the other hand, the most expensive months are March and February, when the average cost of round-trip tickets is $1,050 and $932 respectively.

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Good to know

Low seasonJanuary
Cheapest flight$281
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 3% 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.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $557 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $833.

Reviews of the top airlines 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.
7.4
United AirlinesOverall score based on 9028 reviews
7.7Boarding
8.1Crew
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

10.0 ExcellentJeremy, Nov 2025ORD - DCA
Read more United Airlines reviews

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Even though we were delayed, we were able to make our connection

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Starlink wifi on the Embraer E175 is an excellent experience. I was able to connect and work from IAD all the way to approach into BTV.

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

We were told the flight was delayed 5 times, then it was moved to the next day.

More choices on snacks. Built-in video screen to enjoy entertainment choices.

we landed at cmh ten minutes early but had to sit on tarmac for twenty minutes because a plane was at our gate despite the fact that 3 other gates were open.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We were very rushed by a staff member at the gate when transferring from American Airlines to Fijian. Then the plane stayed put for ages anyhow! The plane was delayed and my bag sent to San Francisco instead of Fiji

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

Information on your arrival and departure airports

Portland (PDX)