$206 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 4/16. 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

Fri, Apr 17 - Wed, Apr 22
Southwest Logo
11:55 pm - 3:00 pm
PDX
-
GCM
13h 05m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$582Southwest
Sun, Apr 26 - Sun, May 3
Southwest Logo
4:25 pm - 12:10 pm
PDX
-
GCM
17h 45m
2 stops
Southwest Logo
12:50 pm - 1:25 am
GCM
-
PDX
14h 35m
2 stops
$637Southwest
Wed, Apr 1 - Sun, Apr 5
Southwest Logo
1:40 pm - 11:25 am
PDX
-
GCM
19h 45m
2 stops
Southwest Logo
12:55 pm - 1:30 am
GCM
-
PDX
14h 35m
2 stops
$662Southwest
Tue, Jun 16 - Sat, Jun 20
Air Canada Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Air Canada Logo
10:55 am - 9:31 am
GCM
-
PDX
24h 36m
2 stops
$669Air Canada
Sun, Mar 29 - Sun, Apr 5
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
5:05 pm - 8:35 pm
GCM
-
PDX
29h 30m
1 stop
$672Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
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
$687Southwest
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
12h 15m
1 stop
Multiple Airlines Logo
1:50 pm - 9:38 pm
GCM
-
PDX
33h 48m
2 stops
$691Multiple Airlines
Thu, May 14 - Sun, May 17
Southwest Logo
5:00 pm - 12:10 pm
PDX
-
GCM
17h 10m
2 stops
Southwest Logo
12:50 pm - 12:05 am
GCM
-
PDX
13h 15m
2 stops
$707Southwest
Sun, Mar 29 - Sun, Apr 5
Southwest Logo
2:10 pm - 10:55 am
PDX
-
GCM
18h 45m
2 stops
Southwest Logo
12:55 pm - 10:35 pm
GCM
-
PDX
11h 40m
2 stops
$712Southwest
Sun, Mar 29 - Sun, Apr 5
Multiple Airlines Logo
3:15 pm - 11:10 am
PDX
-
GCM
41h 55m
2 stops
Multiple Airlines Logo
5:05 pm - 8:35 pm
GCM
-
PDX
29h 30m
1 stop
$714Multiple 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.

Good to know

Low seasonJanuary
Cheapest flight$206
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 44% 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 11392 reviews
6.9Entertainment
6.4Food
7.5Boarding
8.0Crew
7.2Comfort
Airline reviews

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

4.0 OkayPreethi, Mar 2026
SJC - DFW
Read more American Airlines reviews

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

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

Information on your arrival and departure airports