$261 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 4/18. 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

Tue, Jun 16 - Mon, Jun 22
Southwest Logo
7:50 pm - 11:50 am
PDX
-
GCM
14h 00m
2 stops
Southwest Logo
12:45 pm - 1:20 am
GCM
-
PDX
14h 35m
2 stops
$682Southwest
Thu, Apr 23 - Tue, Apr 28
Southwest Logo
2:50 pm - 12:10 pm
PDX
-
GCM
19h 20m
2 stops
Southwest Logo
1:05 pm - 11:10 pm
GCM
-
PDX
12h 05m
2 stops
$707Southwest
Fri, Apr 17 - Tue, Apr 21
Multiple Airlines Logo
7:00 am - 9:35 pm
PDX
-
GCM
12h 35m
1 stop
Multiple Airlines Logo
11:30 am - 8:35 pm
GCM
-
PDX
11h 05m
1 stop
$729Multiple Airlines
Fri, Apr 17 - Tue, Apr 21
Multiple Airlines Logo
11:59 pm - 10:55 am
PDX
-
GCM
32h 56m
2 stops
Multiple Airlines Logo
11:30 am - 8:35 pm
GCM
-
PDX
11h 05m
1 stop
$751Multiple Airlines
Thu, Jun 18 - Tue, Jun 23
Southwest Logo
5:35 pm - 11:50 am
PDX
-
GCM
16h 15m
2 stops
Southwest Logo
12:45 pm - 10:35 pm
GCM
-
PDX
11h 50m
2 stops
$757Southwest
Sat, Apr 18 - Wed, Apr 29
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
11:30 am - 11:59 pm
GCM
-
PDX
14h 29m
2 stops
$767Multiple Airlines
Sat, Apr 18 - Wed, Apr 29
Multiple Airlines Logo
11:59 pm - 10:15 am
PDX
-
GCM
32h 16m
2 stops
Multiple Airlines Logo
11:30 am - 11:59 pm
GCM
-
PDX
14h 29m
2 stops
$770Multiple Airlines
Sat, Apr 18 - Wed, Apr 29
American Airlines Logo
10:23 pm - 11:31 am
PDX
-
GCM
11h 08m
1 stop
American Airlines Logo
12:35 pm - 9:03 pm
GCM
-
PDX
10h 28m
1 stop
$777American Airlines
Sat, Apr 18 - Wed, Apr 29
American Airlines Logo
10:28 pm - 11:00 am
PDX
-
GCM
10h 32m
1 stop
American Airlines Logo
12:35 pm - 11:03 pm
GCM
-
PDX
12h 28m
2 stops
$782American Airlines
Mon, Jun 15 - Sat, Jun 20
American Airlines Logo
12:40 am - 1:35 pm
PDX
-
GCM
10h 55m
1 stop
American Airlines Logo
3:35 pm - 12:50 am
GCM
-
PDX
11h 15m
1 stop
$810American 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 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 $1,211 and $991 respectively.

Good to know

Low seasonJanuary
Cheapest flight$261
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 49% 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 11495 reviews
7.5Boarding
7.9Crew
6.4Food
7.2Comfort
6.9Entertainment
Airline reviews

The flight attendant in business class was excellent! Professional, friendly and attentive.

10.0 ExcellentTy, Mar 2026
MIA - DFW
Read more American Airlines reviews

The flight attendant in business class was excellent! Professional, friendly and attentive.

Delays with no explanation. It could have been handled better.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.

I appreciate that I finally got the seat I paid extra for this time. Thank you

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

I would have liked vegetarian and gluten free options for evening dinner time flight. I would have like a pillow on the international overnight flight . The veg wrap and oaten desert on the international flight was good

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Absolutely terrible. Would never fly American again. 2 deplaned incidents and delayed by close to 24 hours. $12 meal voucher for first class passengers was an insult to the injury. Pathetic.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports