$441 Find Cheap Flights from Portland to Grand Cayman

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 5/31. 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 24% 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, Jun 12 - Thu, Jun 18
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
$687Southwest
Tue, Oct 6 - Sat, Oct 10
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$796Air Canada
Fri, Jun 12 - Thu, Jun 18
Southwest Logo
7:40 pm - 12:10 pm
PDX
-
GCM
14h 30m
2 stops
Southwest Logo
12:50 pm - 1:20 am
GCM
-
PDX
14h 30m
2 stops
$837Southwest
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
2:30 pm - 8:55 pm
PDX
-
GCM
28h 25m
3 stops
Multiple Airlines Logo
12:25 pm - 1:50 pm
GCM
-
PDX
27h 25m
3 stops
$1,029Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
2:30 pm - 8:55 pm
PDX
-
GCM
28h 25m
3 stops
Multiple Airlines Logo
12:25 pm - 1:50 pm
GCM
-
PDX
27h 25m
2 stops
$1,054Multiple Airlines
Fri, Jun 12 - Thu, Jun 18
United Airlines Logo
10:40 pm - 1:30 pm
PDX
-
GCM
12h 50m
1 stop
United Airlines Logo
1:35 pm - 10:48 pm
GCM
-
PDX
11h 13m
1 stop
$1,127United Airlines
Fri, Jun 12 - Thu, Jun 18
Multiple Airlines Logo
5:00 am - 2:50 pm
PDX
-
GCM
31h 50m
3 stops
Multiple Airlines Logo
7:00 am - 12:22 am
GCM
-
PDX
19h 22m
2 stops
$2,472Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
11:27 pm - 12:55 pm
PDX
-
GCM
35h 28m
2 stops
Multiple Airlines Logo
6:05 pm - 5:40 pm
GCM
-
PDX
25h 35m
2 stops
$2,941Multiple Airlines
Fri, Oct 9 - Fri, Oct 23
Delta Logo
9:45 pm - 11:40 am
PDX
-
GCM
11h 55m
1 stop
Delta Logo
12:55 pm - 10:26 pm
GCM
-
PDX
11h 31m
1 stop
$3,818Delta
Fri, Oct 9 - Fri, Oct 23
Delta Logo
9:45 pm - 11:40 am
PDX
-
GCM
11h 55m
1 stop
Delta Logo
12:55 pm - 11:51 pm
GCM
-
PDX
12h 56m
2 stops
$3,823Delta
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 $397, 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$441
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 11641 reviews
6.4Food
7.9Crew
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

8.0 ExcellentAnonymous, May 2026
RSW - ORD
Read more American Airlines reviews

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

Seat bottom cushions are not good. I’m 165# & they hurt my butt. Plenty of legroom.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Portland (PDX)