$276 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 4/17. 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

Tue, Apr 14 - Tue, Apr 21
Southwest Logo
1:35 pm - 12:10 pm
PDX
-
GCM
20h 35m
2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
PDX
11h 55m
2 stops
$538Southwest
Wed, Apr 22 - Wed, Apr 29
Southwest Logo
7:25 pm - 12:10 pm
PDX
-
GCM
14h 45m
2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
PDX
11h 55m
2 stops
$552Southwest
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
12:27 pm - 11:35 am
PDX
-
GCM
21h 08m
2 stops
Multiple Airlines Logo
4:00 pm - 11:50 am
GCM
-
PDX
21h 50m
1 stop
$611Multiple Airlines
Wed, May 13 - Sun, May 17
Southwest Logo
1:35 pm - 12:10 pm
PDX
-
GCM
20h 35m
2 stops
Southwest Logo
12:50 pm - 12:05 am
GCM
-
PDX
13h 15m
2 stops
$623Southwest
Tue, Apr 21 - Sat, May 2
Multiple Airlines Logo
12:38 pm - 4:05 pm
PDX
-
GCM
25h 27m
2 stops
Multiple Airlines Logo
4:00 pm - 11:50 am
GCM
-
PDX
21h 50m
1 stop
$651Multiple Airlines
Mon, Jun 1 - Mon, Jun 8
Southwest Logo
5:00 pm - 12:10 pm
PDX
-
GCM
17h 10m
2 stops
Southwest Logo
12:45 pm - 10:10 pm
GCM
-
PDX
11h 25m
2 stops
$662Southwest
Fri, Apr 10 - Wed, Apr 15
Southwest Logo
11:55 pm - 3:00 pm
PDX
-
GCM
13h 05m
2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
PDX
11h 55m
2 stops
$666Southwest
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
31h 05m
1 stop
Multiple Airlines Logo
11:30 am - 8:35 pm
GCM
-
PDX
11h 05m
1 stop
$668Multiple Airlines
Thu, Apr 9 - Thu, Apr 16
Southwest Logo
4:55 pm - 12:10 pm
PDX
-
GCM
17h 15m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$676Southwest
Tue, Apr 14 - Tue, Apr 21
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
31h 05m
1 stop
Multiple Airlines Logo
11:30 am - 11:44 pm
GCM
-
PDX
14h 14m
2 stops
$693Multiple 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 $1,016 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$276
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 48% 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 11419 reviews
7.9Crew
6.9Entertainment
6.4Food
7.5Boarding
7.2Comfort
Airline reviews

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

2.0 MediocreRussel, Mar 2026
DFW - TPA
Read more American Airlines reviews

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

The crew was excellent and overall the flight was good. No complaints.

I didn't end up taking this flight. I got up at 4am for a flight that was supposed to board at 6am - at 5:55am you delayed the flight to 10am. The airport is under construction so I switched to a later flight as I wasn't going to sit in the airport for 4 hours. They said the delay was due to the crew needing rest from a flight coming in late the night before - if that was the case then I think you should have delayed the flight much sooner so that passengers wouldn't get up so early and get to the airport to sit and wait.

Never had such a lazy first class attendant. Literally spent 60%+ of the flight playing games on her personal phone making up excuses of why she was unavailable.

The flight attendants and the service is getting worse by the day.

Not to have gotten delayed by 2+ hours for the fourth straight American flight. They're the worst.

Like all of the flights I took to get down to Dallas. They were delayed

Other than nearly three hour delay for maintenance issues, everything went smooth

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

The baggage claim experience was poor. The plane crew and the AA app said that checked baggage in CLT would be at carousel 7 but the sign at Baggage Claim said carousel 1. The carousel 1 sign had the correct flight # listed above the belt. But the luggage never came. I went to an AA baggage claim office after about 1 hour and the clerk directed me to another AA room that was poorly marked, with a closed door and no obvious way to know what to do. Finally someone opened the door and my bag was inside. The clerk was totally unable to explain why.

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

Information on your arrival and departure airports

Portland (PDX)