$555 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 9/11. 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
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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, Sep 11 - Sat, Sep 19
Air Canada Logo
10:10 am - 11:30 am
PDX
-
GCM
23h 20m
2 stops
Air Canada Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$555Air Canada
Wed, Oct 28 - Sat, Nov 7
Air Canada Logo
10:00 am - 11:00 am
PDX
-
GCM
23h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$598Air Canada
Fri, Aug 14 - Thu, Aug 27
Multiple Airlines Logo
6:04 pm - 7:10 pm
PDX
-
GCM
23h 06m
1 stop
Multiple Airlines Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$758Multiple Airlines
Fri, Sep 11 - Sat, Sep 19
Multiple Airlines Logo
6:22 pm - 2:50 pm
PDX
-
GCM
18h 28m
3 stops
Multiple Airlines Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$761Multiple Airlines
Fri, Sep 11 - Sat, Sep 19
Multiple Airlines Logo
3:30 pm - 11:30 am
PDX
-
GCM
18h 00m
2 stops
Multiple Airlines Logo
4:00 pm - 9:25 am
GCM
-
PDX
19h 25m
1 stop
$762Multiple Airlines
Fri, Aug 14 - Thu, Aug 27
American Airlines Logo
10:59 pm - 3:08 pm
PDX
-
GCM
14h 09m
1 stop
American Airlines Logo
12:30 pm - 8:31 pm
GCM
-
PDX
10h 01m
1 stop
$781American Airlines
Mon, Aug 10 - Wed, Aug 19
American Airlines Logo
3:00 pm - 11:00 am
PDX
-
GCM
18h 00m
2 stops
American Airlines Logo
2:10 pm - 11:34 am
GCM
-
PDX
23h 24m
2 stops
$786American Airlines
Sat, Jun 20 - Sat, Jun 27
American Airlines Logo
11:43 pm - 1:35 pm
PDX
-
GCM
11h 52m
1 stop
American Airlines Logo
2:17 pm - 11:59 pm
GCM
-
PDX
11h 42m
1 stop
$789American Airlines
Mon, Aug 10 - Wed, Aug 19
Delta Logo
10:55 pm - 11:39 am
PDX
-
GCM
10h 44m
1 stop
Delta Logo
1:04 pm - 9:44 pm
GCM
-
PDX
10h 40m
1 stop
$791Delta
Sat, Jun 20 - Sat, Jun 27
American Airlines Logo
11:43 pm - 1:35 pm
PDX
-
GCM
11h 52m
1 stop
American Airlines Logo
11:22 am - 10:27 pm
GCM
-
PDX
13h 05m
2 stops
$794American 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 $400, 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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$555
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 8% 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 11643 reviews
7.9Crew
7.2Comfort
6.4Food
6.9Entertainment
7.5Boarding
Airline reviews

Movies on my phone are great. It would be nice to have a gluten free snack option.

10.0 ExcellentJolene, May 2026
DFW - FLG
Read more American Airlines reviews

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Portland (PDX)