$196 Find Cheap Flights from Portland to Grand Cayman - Compare and Save

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 Grand Cayman departing on 8/13. 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 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

Tue, Aug 25 - Tue, Sep 1
Delta Logo
6:05 am - 11:39 am
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GCM
6h 34m
1 stop
Delta Logo
1:04 pm - 11:13 pm
GCM
-
PWM
9h 09m
1 stop
$357Delta
Mon, Nov 2 - Mon, Nov 9
Delta Logo
6:01 am - 12:40 pm
PWM
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GCM
6h 39m
1 stop
Delta Logo
1:50 pm - 11:33 pm
GCM
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PWM
9h 43m
1 stop
$357Delta
Wed, Aug 26 - Mon, Aug 31
Delta Logo
6:05 am - 11:39 am
PWM
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GCM
6h 34m
1 stop
Delta Logo
1:04 pm - 11:13 pm
GCM
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PWM
9h 09m
1 stop
$357Delta
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:46 pm - 11:00 am
PWM
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GCM
17h 14m
2 stops
American Airlines Logo
12:30 pm - 10:00 pm
GCM
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PWM
8h 30m
1 stop
$362American Airlines
Fri, Oct 16 - Fri, Oct 23
American Airlines Logo
6:00 am - 11:30 am
PWM
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GCM
6h 30m
1 stop
American Airlines Logo
8:00 am - 11:41 pm
GCM
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PWM
14h 41m
2 stops
$362American Airlines
Thu, Aug 27 - Wed, Sep 2
American Airlines Logo
3:06 pm - 11:00 am
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GCM
20h 54m
2 stops
American Airlines Logo
12:30 pm - 10:00 pm
GCM
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PWM
8h 30m
1 stop
$362American Airlines
Sat, Oct 31 - Mon, Nov 9
United Airlines Logo
5:30 am - 3:35 pm
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GCM
11h 05m
1 stop
United Airlines Logo
5:45 pm - 11:21 pm
GCM
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PWM
29h 36m
2 stops
$482United Airlines
Sat, Oct 31 - Sat, Nov 7
United Airlines Logo
5:30 am - 3:35 pm
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GCM
11h 05m
1 stop
United Airlines Logo
2:55 pm - 9:00 am
GCM
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PWM
18h 05m
2 stops
$482United Airlines
Wed, Nov 4 - Sat, Nov 7
Multiple Airlines Logo
6:31 pm - 5:20 pm
PWM
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GCM
22h 49m
1 stop
Multiple Airlines Logo
11:25 am - 5:51 pm
GCM
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PWM
6h 26m
1 stop
$537Multiple Airlines
Sat, Oct 31 - Sat, Nov 7
Multiple Airlines Logo
6:31 pm - 5:20 pm
PWM
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GCM
23h 49m
1 stop
Multiple Airlines Logo
11:25 am - 5:51 pm
GCM
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PWM
6h 26m
1 stop
$564Multiple Airlines
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 $383, 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 July, when tickets cost $0 (return) on average. On the other hand, the most expensive months are April and August, when the average cost of round-trip tickets is $828 and $742 respectively.

Good to know

Low season

June

Cheapest flight

$196
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 13% 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 3 airlines serving 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.
7.8
DeltaOverall score based on 8483 reviews
7.8Entertainment
8.5Crew
7.8Comfort
7.2Food
8.1Boarding
Airline reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

4.0 OkayNoel, Aug 2026
LAS - BOS
Read more Delta reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

The flight was over 2 hours late.. once we finally got boarded things were fine

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

The flight was delayed 4 hours, and when we finally boarded, they told us that the fuel was only just then checked. So, we waited even longer to take off.

With a 24 hour delay, the Flight stared off rough. They had a nationwide IT Outage but communications to Passengers was very bad. Ground Staff and Ticket Agents were extremely rude and unhelpful. Perhaps they should take ground training from DL or Qatar. The food was horrible. Seafood was mixed with Bacon. Those two don’t have any space for Jewish or Muslim Faith Customers. The Airline needs new management.

Great. Clean. Seats comfortable. Food was free. Had new release movies.

The airplane I love and I love I came back safe thank you American airlines

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

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

Flight left more than 5 hours late. American's policy did not allow flight to be fueled or bags to be loaded due to intermittent lightning. We were on the plane for hours before having to deplane. They then changed the departure time to an earlier than expected time. We re-boarded and had to wait another 1.5 hours on the plane before it finally took off. Flight crew did not serve any food or drinks while airborne.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports