$682 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 11/3. 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, Nov 3 - Wed, Nov 11
Southwest Logo
1:00 pm - 12:35 pm
PDX
-
GCM
20h 35m
2 stops
Southwest Logo
1:30 pm - 11:15 pm
GCM
-
PDX
12h 45m
2 stops
$682Southwest
Tue, Jul 7 - Sun, Jul 12
Southwest Logo
9:20 pm - 11:55 am
PDX
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 12:15 am
GCM
-
PDX
13h 25m
2 stops
$687Southwest
Wed, Sep 16 - Thu, Sep 24
Air Canada Logo
3:30 pm - 11:30 am
PDX
-
GCM
18h 00m
2 stops
Air Canada Logo
12:25 pm - 9:31 am
GCM
-
PDX
23h 06m
2 stops
$698Air Canada
Tue, Sep 15 - Thu, Sep 24
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
$712Air Canada
Mon, Aug 17 - Sat, Aug 22
Multiple Airlines Logo
6:19 am - 4:05 pm
PDX
-
GCM
31h 46m
2 stops
Multiple Airlines Logo
4:00 pm - 11:41 am
GCM
-
PDX
21h 41m
1 stop
$724Multiple Airlines
Tue, Nov 3 - Wed, Nov 11
Air Canada Logo
10:00 am - 12:00 pm
PDX
-
GCM
23h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$750Air Canada
Sat, Nov 21 - Fri, Nov 27
Air Canada Logo
10:00 am - 12:00 pm
PDX
-
GCM
23h 00m
2 stops
Air Canada Logo
1:10 pm - 9:26 am
GCM
-
PDX
23h 16m
2 stops
$756Air Canada
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
7:40 pm - 11:55 am
PDX
-
GCM
14h 15m
2 stops
Southwest Logo
12:50 pm - 12:10 am
GCM
-
PDX
13h 20m
2 stops
$757Southwest
Wed, Aug 19 - Sat, Aug 22
Multiple Airlines Logo
5:42 pm - 11:35 am
PDX
-
GCM
15h 53m
2 stops
Multiple Airlines Logo
4:00 pm - 11:41 am
GCM
-
PDX
21h 41m
1 stop
$764Multiple Airlines
Thu, Sep 17 - Sun, Sep 27
Multiple Airlines Logo
7:45 pm - 11:30 am
PDX
-
GCM
37h 45m
2 stops
Multiple Airlines Logo
6:10 pm - 12:59 pm
GCM
-
PDX
20h 49m
1 stop
$777Multiple 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 $410, 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$682
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 7% 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 11636 reviews
7.5Boarding
6.9Entertainment
7.9Crew
6.4Food
7.2Comfort
Airline reviews

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

4.0 OkayAnonymous, Jun 2026
DEN - ORD
Read more American Airlines reviews

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

It wa sort of on time; the cab was left with some trash

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports