$572 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 11/3. 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

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
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Best Grand Cayman Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$572
George Town
George Town2 stops$572

Cheap Flights from Portland to Grand Cayman

 
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

Mon, Nov 3 - Mon, Nov 10
Southwest Logo
3:55 pm - 12:35 pmPDX-GCM
17h 40m2 stops
Southwest Logo
1:30 pm - 12:15 amGCM-PDX
13h 45m2 stops
$572Southwest
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Tue, Jul 22 - Wed, Jul 30
Southwest Logo
9:15 pm - 11:50 amPDX-GCM
12h 35m2 stops
Southwest Logo
12:45 pm - 11:50 pmGCM-PDX
13h 05m2 stops
$640Southwest
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Tue, Jul 1 - Wed, Jul 9
 Logo
6:39 pm - 4:10 pmPDX-GCM
19h 31m3 stops
 Logo
11:30 am - 2:15 pmGCM-PDX
28h 45m2 stops
Tue, Jul 22 - Wed, Jul 30
Delta Logo
9:30 pm - 11:22 amPDX-GCM
11h 52m1 stop
Delta Logo
12:37 pm - 11:59 pmGCM-PDX
13h 22m1 stop
$666Delta
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Fri, Oct 10 - Sat, Oct 18
United Airlines Logo
11:55 pm - 12:30 pmPDX-GCM
10h 35m1 stop
United Airlines Logo
1:35 pm - 9:00 amGCM-PDX
21h 25m2 stops
$670United Airlines
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Mon, Nov 3 - Mon, Nov 10
United Airlines Logo
11:59 pm - 4:25 pmPDX-GCM
13h 26m2 stops
United Airlines Logo
5:35 pm - 6:36 pmGCM-PDX
28h 01m1 stop
$688United Airlines
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Tue, Jul 22 - Wed, Jul 30
 Logo
3:10 pm - 4:10 pmPDX-GCM
23h 00m3 stops
 Logo
11:30 am - 2:15 pmGCM-PDX
28h 45m2 stops
Tue, Jul 1 - Wed, Jul 9
 Logo
6:39 pm - 4:10 pmPDX-GCM
19h 31m3 stops
 Logo
11:30 am - 2:15 pmGCM-PDX
28h 45m3 stops
Mon, Nov 3 - Mon, Nov 10
American Airlines Logo
11:13 pm - 7:51 pmPDX-GCM
17h 38m1 stop
American Airlines Logo
4:15 pm - 11:07 pmGCM-PDX
9h 52m1 stop
$785American Airlines
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Mon, Nov 3 - Mon, Nov 10
American Airlines Logo
11:59 pm - 1:55 pmPDX-GCM
10h 56m2 stops
American Airlines Logo
2:20 pm - 11:07 pmGCM-PDX
11h 47m1 stop
$789American Airlines
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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 $769, 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 January, when tickets cost $566 (return) on average. On the other hand, the most expensive months are February and April, when the average cost of round-trip tickets is $853 and $838 respectively.


Good to know

Low seasonAugust
High seasonApril
Cheapest flight$572
Best time to beat the crowds but there is an average 8% increase in price.
Most popular time to fly with an average 14% increase in price.
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.

  • What is the cheapest time of day to fly to Grand Cayman?

    The cheapest time of day to fly to Grand Cayman 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 Grand Cayman is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $833.

Top airlines 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.
7.4
United AirlinesOverall score based on 8801 reviews
6.6Food
8.1Crew
7.0Entertainment
7.7Boarding
7.3Comfort
Airline reviews

Gate agent did not hold flight for connection, provided no assistance to get new flight

2.0 MediocreJack, Jun 2025SAT - IAH
Read more United Airlines reviews

Gate agent did not hold flight for connection, provided no assistance to get new flight

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

United airlines, mediocre at best. No issues , nothing great . Worked for me

Boarding experience was smooth. Flight attendants were friendly and helpful. Entertainment system on the Houston-Edmonton flight did not function for passengers on the left side of the aisle. On the bird's eye flight from Quito to Houston, they should not serve a meal. No one needs to eat after midnight and it is disturbing for those passengers trying to sleep.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Everything you need to know for your flight to Grand Cayman

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