$264 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

Wed, Jan 21 - Tue, Feb 3
Multiple Airlines Logo
7:18 am - 1:53 pm
PDX
-
GCM
27h 35m2 stops
Multiple Airlines Logo
11:30 am - 8:27 pm
GCM
-
PDX
11h 57m1 stop
$548Multiple Airlines
Sun, Jan 11 - Thu, Jan 15
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 2:40 pm
GCM
-
PDX
52h 10m2 stops
$559Air Canada
Sun, Jan 25 - Tue, Feb 3
Multiple Airlines Logo
11:09 am - 1:44 pm
PDX
-
GCM
23h 35m2 stops
Multiple Airlines Logo
11:30 am - 8:27 pm
GCM
-
PDX
11h 57m1 stop
$563Multiple Airlines
Sun, Jan 11 - Thu, Jan 15
Southwest Logo
4:15 pm - 12:55 pm
PDX
-
GCM
17h 40m2 stops
Southwest Logo
1:50 pm - 10:30 pm
GCM
-
PDX
11h 40m2 stops
$565Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:00 pm - 12:10 pm
PDX
-
GCM
17h 10m2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
PDX
11h 55m2 stops
$572Southwest
Mon, Jan 26 - Tue, Feb 3
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m1 stop
Multiple Airlines Logo
11:30 am - 8:27 pm
GCM
-
PDX
11h 57m1 stop
$574Multiple Airlines
Sun, Jan 11 - Thu, Jan 15
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m2 stops
$581Air Canada
Sat, Jan 24 - Thu, Jan 29
Multiple Airlines Logo
7:05 am - 2:00 pm
PDX
-
GCM
27h 55m1 stop
Multiple Airlines Logo
2:49 pm - 4:44 pm
GCM
-
PDX
28h 55m2 stops
$583Multiple Airlines
Wed, Jan 21 - Thu, Jan 29
Multiple Airlines Logo
7:05 am - 2:00 pm
PDX
-
GCM
27h 55m1 stop
Multiple Airlines Logo
2:49 pm - 4:44 pm
GCM
-
PDX
28h 55m2 stops
$588Multiple Airlines
Tue, Jan 20 - Tue, Feb 3
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m2 stops
$590Air Canada
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 December, when the average cost of round-trip tickets is $1,142 and $1,077 respectively.

Good to know

Low seasonJanuary
Cheapest flight$264
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 1% 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.

  • 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 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 11052 reviews
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

6.0 GoodDan, Dec 2025
ORD - ALO
Read more American Airlines reviews

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

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

Information on your arrival and departure airports