$612 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 12/6. 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

Sun, Dec 6 - Sun, Dec 13
Southwest Logo
8:10 pm - 12:35 pm
PDX
-
GCM
13h 25m
2 stops
Southwest Logo
1:30 pm - 10:40 am
GCM
-
PDX
24h 10m
2 stops
$612Southwest
Sat, Oct 17 - Sat, Oct 24
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 9:26 am
GCM
-
PDX
23h 01m
2 stops
$644Air Canada
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
7:18 am - 9:15 pm
PDX
-
GCM
10h 57m
1 stop
Multiple Airlines Logo
7:00 am - 8:50 pm
GCM
-
PDX
16h 50m
1 stop
$675Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
10:00 am - 12:10 pm
PDX
-
GCM
23h 10m
2 stops
Multiple Airlines Logo
4:45 pm - 8:50 pm
GCM
-
PDX
31h 05m
1 stop
$695Multiple Airlines
Mon, Jul 20 - Mon, Jul 27
Southwest Logo
9:20 pm - 11:55 am
PDX
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 1:25 am
GCM
-
PDX
14h 35m
2 stops
$707Southwest
Thu, Aug 13 - Tue, Aug 18
Multiple Airlines Logo
6:19 am - 9:15 pm
PDX
-
GCM
12h 56m
2 stops
Multiple Airlines Logo
11:30 am - 11:59 pm
GCM
-
PDX
14h 29m
2 stops
$725Multiple Airlines
Sun, Dec 6 - Mon, Dec 7
Multiple Airlines Logo
5:00 am - 9:15 pm
PDX
-
GCM
13h 15m
2 stops
Multiple Airlines Logo
1:10 pm - 2:41 pm
GCM
-
PDX
28h 31m
2 stops
$759Multiple Airlines
Thu, Oct 8 - Sat, Oct 17
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Air Canada Logo
12:25 pm - 7:06 pm
GCM
-
PDX
32h 41m
2 stops
$775Air Canada
Mon, Jul 20 - Mon, Jul 27
American Airlines Logo
9:47 pm - 11:25 am
PDX
-
GCM
11h 38m
1 stop
American Airlines Logo
12:33 pm - 8:40 pm
GCM
-
PDX
10h 07m
1 stop
$781American Airlines
Thu, Jul 30 - Tue, Aug 4
American Airlines Logo
5:28 pm - 11:00 am
PDX
-
GCM
15h 32m
2 stops
American Airlines Logo
12:33 pm - 8:45 pm
GCM
-
PDX
10h 12m
1 stop
$786American 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 $421, 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.

Good to know

Low seasonJanuary
Cheapest flight$612
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 11% 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 11746 reviews
7.2Comfort
6.8Entertainment
6.4Food
7.9Crew
7.5Boarding
Airline reviews

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

10.0 ExcellentAnonymous, Jun 2026
LGA - MIA
Read more American Airlines reviews

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

Maybe focus more on delivering a good product vs selling me a damn credit card

American Airlines is a great dependable airline, on time arrival and departure with polite crew and staff.

I think since I am an AA Advantage member, my checked bags should have been free, but I paid for all 4 of us.

This flight moved Gates several times in a short time period, from B to C, which required a substantial walk or rail ride. Then the flight was delayed more than 2 hours and the food was subpar compared to other flights.

Flight was delayed multiple times without giving any particular reason and the only thing that was communicated was that 'Aircraft is getting ready'. I was stuck at SFO airport for 15 hours and finally took Southwest Airlines flight back home to Dallas.

Hydraulic leak caused the flight to be cancelled. Auto system scheduled us on a 3 am flight. Wevhsedvrebook on the app and hit schedules later in the afternoon. Our luggage per gate and ticket agent would be rescanned and put in our new flight. Did not happen. Our luggage stayed in hsv. Baggage claim in wash dc unable to help. We filed a claim. Several emails about our luggage were in conflict with one another. Called as baggage and was on hold 30 minutes. Oscar said one of 2 was out fir delivery then cancelled. About 45 minutes later both pieces were delivered. Their system is suspect

I was not clear if food was offered or not.

Because I bought my ticket from Underpricer, I could not check in online. I could only check in at the airport and that was deeply frustrating because I had to arrive very early. The flight also departed 45 min late and passengers were given no explanations about why we were delayed. I was worried I would miss my connecting flight. Once on board, however, the flight was fine.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports