$248 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 6/1. 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

Tue, Sep 22 - Thu, Oct 1
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$573Air Canada
Fri, May 15 - Wed, May 20
Southwest Logo
2:50 pm - 12:05 pm
PDX
-
GCM
19h 15m
2 stops
Southwest Logo
1:05 pm - 11:00 pm
GCM
-
PDX
11h 55m
2 stops
$651Southwest
Sun, May 3 - Thu, May 7
Southwest Logo
4:25 pm - 12:10 pm
PDX
-
GCM
17h 45m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$668Southwest
Fri, May 22 - Fri, May 29
Southwest Logo
11:55 pm - 3:00 pm
PDX
-
GCM
13h 05m
2 stops
Southwest Logo
1:05 pm - 12:25 am
GCM
-
PDX
13h 20m
2 stops
$707Southwest
Mon, May 4 - Mon, May 11
Southwest Logo
5:00 pm - 12:10 pm
PDX
-
GCM
17h 10m
2 stops
Southwest Logo
1:05 pm - 10:40 pm
GCM
-
PDX
11h 35m
2 stops
$743Southwest
Mon, May 4 - Sat, May 9
Multiple Airlines Logo
11:58 am - 4:05 pm
PDX
-
GCM
26h 07m
2 stops
Multiple Airlines Logo
4:00 pm - 11:50 am
GCM
-
PDX
21h 50m
1 stop
$756Multiple Airlines
Thu, Apr 30 - Sat, May 9
Multiple Airlines Logo
11:58 am - 4:05 pm
PDX
-
GCM
26h 07m
2 stops
Multiple Airlines Logo
4:00 pm - 11:50 am
GCM
-
PDX
21h 50m
1 stop
$775Multiple Airlines
Sun, May 3 - Thu, May 7
Delta Logo
11:06 pm - 12:00 pm
PDX
-
GCM
10h 54m
1 stop
Delta Logo
1:19 pm - 9:46 pm
GCM
-
PDX
10h 27m
1 stop
$777Delta
Fri, May 1 - Sat, May 9
Multiple Airlines Logo
9:54 am - 7:10 pm
PDX
-
GCM
31h 16m
2 stops
Multiple Airlines Logo
4:00 pm - 11:50 am
GCM
-
PDX
21h 50m
1 stop
$778Multiple Airlines
Sun, May 3 - Wed, May 6
Delta Logo
6:05 pm - 12:00 pm
PDX
-
GCM
15h 55m
2 stops
Delta Logo
1:25 pm - 8:37 am
GCM
-
PDX
21h 12m
2 stops
$782Delta
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 $1,230 and $991 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$248
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 5% 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.
7.1
American AirlinesOverall score based on 11546 reviews
7.5Boarding
7.2Comfort
7.9Crew
6.9Entertainment
6.4Food
Airline reviews

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

2.0 MediocreGerrilu, Apr 2026
CLT - PIT
Read more American Airlines reviews

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We did not have enough time to make our connecting flight. As a result, we were put onto a different airline for our second leg. The different airline was NOT comparable to British Airlines, and our arrival was significantly delayed. The actual flight on BA was amazing.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

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

Information on your arrival and departure airports

Portland (PDX)