$306 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 4/12. 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

Sat, Apr 18 - Wed, Apr 29
Southwest Logo
2:40 pm - 11:55 am
PDX
-
GCM
19h 15m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$557Southwest
Mon, Jul 20 - Wed, Jul 29
Southwest Logo
7:55 pm - 11:50 am
PDX
-
GCM
13h 55m
2 stops
Southwest Logo
12:45 pm - 10:35 pm
GCM
-
PDX
11h 50m
2 stops
$662Southwest
Wed, May 6 - Sat, May 9
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
13h 45m
2 stops
Air Canada Logo
12:25 pm - 9:30 am
GCM
-
PDX
23h 05m
2 stops
$678Air Canada
Tue, Mar 24 - Tue, Mar 31
Southwest Logo
6:00 pm - 11:45 am
PDX
-
GCM
15h 45m
2 stops
Southwest Logo
11:50 am - 10:10 pm
GCM
-
PDX
12h 20m
2 stops
$687Southwest
Tue, Mar 24 - Mon, Mar 30
Air Canada Logo
7:05 pm - 11:25 am
PDX
-
GCM
38h 20m
2 stops
Air Canada Logo
11:25 am - 6:30 pm
GCM
-
PDX
33h 05m
2 stops
$690Air Canada
Wed, Mar 4 - Mon, Mar 9
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m
2 stops
Air Canada Logo
11:30 am - 9:15 am
GCM
-
PDX
23h 45m
2 stops
$705Air Canada
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
7:45 pm - 11:30 am
PDX
-
GCM
13h 45m
2 stops
Multiple Airlines Logo
4:00 pm - 9:38 am
GCM
-
PDX
19h 38m
1 stop
$707Multiple Airlines
Sat, Apr 18 - Wed, Apr 29
United Airlines Logo
11:59 pm - 12:45 pm
PDX
-
GCM
10h 46m
1 stop
United Airlines Logo
1:50 pm - 10:29 pm
GCM
-
PDX
10h 39m
1 stop
$717United Airlines
Fri, Apr 17 - Wed, Apr 29
American Airlines Logo
12:59 am - 3:03 pm
PDX
-
GCM
12h 04m
2 stops
American Airlines Logo
12:35 pm - 9:03 pm
GCM
-
PDX
10h 28m
1 stop
$722American Airlines
Wed, Mar 4 - Mon, Mar 9
Air Canada Logo
3:15 pm - 12:25 pm
PDX
-
GCM
18h 10m
2 stops
Air Canada Logo
11:30 am - 2:40 pm
GCM
-
PDX
29h 10m
2 stops
$739Air Canada
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 $370, 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 $666 (return) on average. On the other hand, the most expensive months are March and June, when the average cost of round-trip tickets is $1,161 and $915 respectively.

Good to know

Low seasonJanuary
Cheapest flight$260
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 41% 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.

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.
7.2
American AirlinesOverall score based on 11339 reviews
6.4Food
8.0Crew
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

Never ontime and always delays. Long waits for customer service and often app doesn’t work

6.0 GoodGovinda, Feb 2026
DFW - MSN
Read more American Airlines reviews

Never ontime and always delays. Long waits for customer service and often app doesn’t work

Arriving plane went to wrong gate. Flight Attendant was late. Was in no Hurry when he arrived. Flight was fine. Plane had to wait 20 minutes to get assigned a gate due to designated gate tied up. barely connected.. Boarded extremely late on final leg of trip.

We arrived 25 minutes early only to be told our gate was occupied and so we sat for close to 30 minutes to pull into a gate. That’s not an early arrival!

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

The TSA check in took 1.5 hours to get through in Austin and I missed my flights back to DC

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

There was free WiFi (definitely a plus), but the flight was delayed 45 minutes waiting on a catering truck that never arrived. The pilot said there would be food vouchers given out at the end of the gangway to make up for the inconvenience, but there was no one offering those. Delay made me late for work!

Waiting for gate in RDU for more than 20mins is crazy.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports