$644 Find Cheap Flights from Portland to Grand Cayman

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Grand Cayman departing on 10/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to Grand Cayman, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Book Cheap Portland to Grand Cayman 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 Grand Cayman 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 Grand Cayman

Fri, Oct 16 - Sat, Oct 24
Air Canada Logo
3:30 pm - 11:30 am
PDX
-
GCM
18h 00m
2 stops
Air Canada Logo
12:25 pm - 2:41 pm
GCM
-
PDX
28h 16m
2 stops
$644Air Canada
Fri, Oct 16 - Sun, Oct 25
Air Canada Logo
3:30 pm - 11:30 am
PDX
-
GCM
18h 00m
2 stops
Air Canada Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$649Air Canada
Sat, Oct 17 - Sat, Oct 24
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 2:41 pm
GCM
-
PDX
28h 16m
2 stops
$655Air Canada
Sat, Oct 17 - Sun, Oct 25
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$659Air Canada
Sat, Oct 31 - Sun, Nov 8
Air Canada Logo
10:00 am - 12:00 pm
PDX
-
GCM
24h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$678Air Canada
Fri, Jul 10 - Thu, Jul 16
Southwest Logo
9:20 pm - 10:30 am
PDX
-
GCM
11h 10m
1 stop
Southwest Logo
12:50 pm - 11:55 pm
GCM
-
PDX
13h 05m
2 stops
$687Southwest
Fri, Jul 17 - Sun, Jul 19
Southwest Logo
9:20 pm - 10:30 am
PDX
-
GCM
11h 10m
1 stop
Southwest Logo
12:50 pm - 12:15 am
GCM
-
PDX
13h 25m
2 stops
$692Southwest
Fri, Nov 20 - Fri, Nov 27
Air Canada Logo
10:00 am - 12:00 pm
PDX
-
GCM
23h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$695Air Canada
Thu, Sep 17 - Sun, Sep 27
Multiple Airlines Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Multiple Airlines Logo
6:10 pm - 12:59 pm
GCM
-
PDX
20h 49m
1 stop
$734Multiple Airlines
Fri, Jun 26 - Fri, Jul 3
Southwest Logo
9:20 pm - 10:30 am
PDX
-
GCM
11h 10m
1 stop
Southwest Logo
12:50 pm - 12:30 am
GCM
-
PDX
13h 40m
2 stops
$752Southwest
Booking Insights

KAYAK's insights & trends for Portland to Grand Cayman flights

Get data-powered insights and trends into flights from Portland to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Portland to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $415, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Portland to Grand Cayman?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Grand Cayman, 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 Grand Cayman is December, when tickets cost $665 (return) on average. On the other hand, the most expensive months are October and June, when the average cost of round-trip tickets is $948 and $781 respectively.

Good to know

Low seasonJanuary
Cheapest flight$644
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Portland to George Town

FAQs - booking Grand Cayman flights

  • How does KAYAK find such low prices on flights from Portland to Grand Cayman?

    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 Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from Portland to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Grand Cayman? 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 11668 reviews
7.5Boarding
7.9Crew
6.4Food
7.2Comfort
6.8Entertainment
Airline reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

2.0 MediocreUzair, Jun 2026
SFO - JFK
Read more American Airlines reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Crew were professional and kind. The flight was smooth. But... The internet, which we paid 35 dollars for, did not work for most of the flight. This made providing media for our child an uncomfortable hassle.

Overall fine. Seemed like one of the older model planes? Crew was mostly very kind, though some of the female attendants were a rather abrupt during the food service.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports