$232 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 2/18. 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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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

Mon, Mar 2 - Thu, Mar 5
Southwest Logo
4:15 pm - 12:55 pm
PDX
-
GCM
17h 40m
2 stops
Southwest Logo
1:40 pm - 12:45 am
GCM
-
PDX
14h 05m
2 stops
$487Southwest
Mon, Mar 2 - Thu, Mar 5
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
11h 15m
1 stop
Multiple Airlines Logo
2:49 pm - 3:48 pm
GCM
-
PDX
27h 59m
2 stops
$550Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m
2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$593Air Canada
Mon, Mar 2 - Thu, Mar 5
Air Canada Logo
9:50 am - 12:25 pm
PDX
-
GCM
23h 35m
2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m
2 stops
$596Air Canada
Mon, Mar 2 - Thu, Mar 5
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m
1 stop
Multiple Airlines Logo
7:00 am - 8:44 pm
GCM
-
PDX
16h 44m
1 stop
$610Multiple Airlines
Sun, Apr 12 - Fri, Apr 17
Southwest Logo
5:50 pm - 12:10 pm
PDX
-
GCM
16h 20m
2 stops
Southwest Logo
1:05 pm - 10:40 pm
GCM
-
PDX
11h 35m
2 stops
$654Southwest
Sun, Apr 12 - Fri, Apr 17
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
7:00 am - 8:35 pm
GCM
-
PDX
15h 35m
1 stop
$676Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Air Canada Logo
7:05 pm - 12:25 pm
PDX
-
GCM
14h 20m
2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m
2 stops
$683Air Canada
Sat, Mar 14 - Sat, Mar 21
American Airlines Logo
10:53 pm - 7:15 pm
PDX
-
GCM
18h 22m
1 stop
American Airlines Logo
7:45 am - 11:44 pm
GCM
-
PDX
17h 59m
1 stop
$687American Airlines
Fri, Mar 13 - Fri, Mar 20
Multiple Airlines Logo
9:26 pm - 6:00 pm
PDX
-
GCM
42h 34m
2 stops
Multiple Airlines Logo
8:00 am - 8:50 pm
GCM
-
PDX
14h 50m
1 stop
$724Multiple 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$232
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 11205 reviews
6.4Food
8.0Crew
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

4.0 OkayBrandle, Jan 2026
DFW - MCO
Read more American Airlines reviews

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

My flight to London from Philadelphia was cancelled due to weather.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

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

Information on your arrival and departure airports

Portland (PDX)