$282 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 2/27. 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, Mar 1 - Thu, Mar 5
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
42h 10m
2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m
2 stops
$564Air Canada
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
$582Multiple Airlines
Wed, Apr 8 - Sun, Apr 12
Air Canada Logo
7:05 pm - 11:10 am
PDX
-
GCM
14h 05m
2 stops
Air Canada Logo
12:30 pm - 9:15 am
GCM
-
PDX
46h 45m
2 stops
$596Air Canada
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 - 11:44 pm
GCM
-
PDX
32h 59m
2 stops
$650Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Air Canada Logo
7:05 pm - 11:25 am
PDX
-
GCM
14h 20m
2 stops
Air Canada Logo
11:30 am - 9:15 am
GCM
-
PDX
23h 45m
2 stops
$656Air Canada
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
12:30 pm - 9:15 am
GCM
-
PDX
46h 45m
2 stops
$674Multiple Airlines
Mon, Jul 20 - Wed, Jul 29
American Airlines Logo
12:59 am - 1:32 pm
PDX
-
GCM
10h 33m
1 stop
American Airlines Logo
2:40 pm - 12:48 am
GCM
-
PDX
12h 08m
1 stop
$687American Airlines
Tue, Jul 21 - Wed, Jul 29
American Airlines Logo
11:59 pm - 1:10 pm
PDX
-
GCM
11h 11m
2 stops
American Airlines Logo
2:40 pm - 10:50 pm
GCM
-
PDX
10h 10m
1 stop
$692American Airlines
Tue, Jul 21 - Wed, Jul 29
Delta Logo
3:50 pm - 11:26 am
PDX
-
GCM
17h 36m
2 stops
Delta Logo
12:40 pm - 11:53 pm
GCM
-
PDX
13h 13m
2 stops
$712Delta
Wed, Apr 8 - Sun, Apr 12
Multiple Airlines Logo
7:05 pm - 3:25 pm
PDX
-
GCM
18h 20m
3 stops
Multiple Airlines Logo
12:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$723Multiple 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 $1,179 and $915 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$282
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 6% 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.
7.2
American AirlinesOverall score based on 11193 reviews
7.5Boarding
7.2Comfort
6.4Food
6.9Entertainment
8.0Crew
Airline reviews

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

8.0 ExcellentAnonymous, Jan 2026
PHX - CMH
Read more American Airlines reviews

one crew said "he" didn't serve double alcohol drinks for travelers in exit rows. crew on prior flight did. Is this a AA rule, and the prior crew was being nice? Also, I think we deserve more than a 25% refund for losing first class seats when rescheduling a flight due to weather

It was a little concerning to hear the ground crew arguing with the flight crew over baggage space. Instead of taking them and checking them, they started checking for space in the first class cabin moving items around like the flight crew didn't know what they were doing. I was embarrassed for them.

2 hour delay due to equipment failure. No updates via the app and airport screens (which continued to show a departure time in the past). AA eventually switched planes and the new plane was not catered or cleaned correctly.

I booked an aisle seat and was given a middle. At 6'4" 230lbs, it is not ideal to fly in the middle row for myself and passengers.

Trip delayed for 2 hours because of rain. We boarded and have to get down the flight and reboard again.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

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

Information on your arrival and departure airports

Portland (PDX)