$176 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 4/15. 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, Apr 17 - Wed, Apr 22
Southwest Logo
11:55 pm - 3:00 pm
PDX
-
GCM
13h 05m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$582Southwest
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
12h 15m
1 stop
Multiple Airlines Logo
4:45 pm - 8:35 pm
GCM
-
PDX
29h 50m
1 stop
$595Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
12h 15m
1 stop
Multiple Airlines Logo
1:50 pm - 9:38 pm
GCM
-
PDX
33h 48m
2 stops
$611Multiple Airlines
Sun, Apr 26 - Sun, May 3
Southwest Logo
4:25 pm - 12:10 pm
PDX
-
GCM
17h 45m
2 stops
Southwest Logo
12:50 pm - 1:25 am
GCM
-
PDX
14h 35m
2 stops
$637Southwest
Wed, Apr 1 - Sun, Apr 5
Southwest Logo
1:40 pm - 11:25 am
PDX
-
GCM
19h 45m
2 stops
Southwest Logo
12:55 pm - 1:30 am
GCM
-
PDX
14h 35m
2 stops
$662Southwest
Tue, Jun 16 - Sat, Jun 20
Air Canada Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Air Canada Logo
10:55 am - 9:31 am
GCM
-
PDX
24h 36m
2 stops
$669Air Canada
Sun, Mar 29 - Sun, Apr 5
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
5:05 pm - 8:35 pm
GCM
-
PDX
29h 30m
1 stop
$672Multiple Airlines
Mon, Apr 13 - Mon, Apr 20
Southwest Logo
4:55 pm - 12:10 pm
PDX
-
GCM
17h 15m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$687Southwest
Mon, Apr 13 - Mon, Apr 20
Multiple Airlines Logo
7:00 am - 9:15 pm
PDX
-
GCM
12h 15m
1 stop
Multiple Airlines Logo
1:50 pm - 9:38 pm
GCM
-
PDX
33h 48m
2 stops
$691Multiple Airlines
Tue, Jun 16 - Sat, Jun 20
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
$711Air 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 $374, 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 $1,179 and $915 respectively.

Good to know

Low seasonJanuary
Cheapest flight$176
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 44% 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.
7.1
American AirlinesOverall score based on 11379 reviews
6.9Entertainment
6.4Food
8.0Crew
7.5Boarding
7.2Comfort
Airline reviews

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

8.0 ExcellentCatherine, Mar 2026
STL - LGA
Read more American Airlines reviews

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports