$157 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 2/6. 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, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
25h 35m
1 stop
Multiple Airlines Logo
2:49 pm - 3:48 pm
GCM
-
PDX
27h 59m
2 stops
$591Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
25h 35m
1 stop
Multiple Airlines Logo
7:00 am - 8:44 pm
GCM
-
PDX
16h 44m
1 stop
$621Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
7:05 pm - 12:25 pm
PDX
-
GCM
14h 20m
2 stops
Multiple Airlines Logo
5:25 pm - 2:40 pm
GCM
-
PDX
24h 15m
2 stops
$648Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
7:05 pm - 12:25 pm
PDX
-
GCM
14h 20m
2 stops
Multiple Airlines Logo
5:25 pm - 6:30 pm
GCM
-
PDX
28h 05m
3 stops
$654Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Southwest Logo
7:00 pm - 11:45 am
PDX
-
GCM
14h 45m
2 stops
Southwest Logo
12:20 pm - 11:10 pm
GCM
-
PDX
12h 50m
2 stops
$662Southwest
Sun, Mar 1 - Sun, Mar 8
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
25h 35m
1 stop
Multiple Airlines Logo
8:00 am - 8:33 pm
GCM
-
PDX
14h 33m
1 stop
$664Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
7:05 pm - 11:25 am
PDX
-
GCM
14h 20m
2 stops
Multiple Airlines Logo
8:00 am - 8:50 pm
GCM
-
PDX
14h 50m
1 stop
$669Multiple Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
Multiple Airlines Logo
8:00 am - 8:50 pm
GCM
-
PDX
14h 50m
1 stop
$685Multiple Airlines
Fri, Feb 13 - Fri, Feb 20
United Airlines Logo
6:57 pm - 4:20 pm
PDX
-
GCM
18h 23m
2 stops
United Airlines Logo
2:50 pm - 10:40 pm
GCM
-
PDX
10h 50m
1 stop
$687United Airlines
Tue, Feb 10 - Sun, Feb 15
American Airlines Logo
10:15 pm - 11:26 am
PDX
-
GCM
10h 11m
1 stop
American Airlines Logo
3:35 pm - 12:17 am
GCM
-
PDX
11h 42m
1 stop
$692American 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 $343, 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 February, when the average cost of round-trip tickets is $1,179 and $932 respectively.

Good to know

Low seasonJanuary
Cheapest flight$157
Best time to beat the crowds with an average 20% 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.
7.2
American AirlinesOverall score based on 11136 reviews
7.2Comfort
7.5Boarding
8.0Crew
6.9Entertainment
6.4Food
Airline reviews

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

6.0 GoodJennifer, Jan 2026
DFW - BOS
Read more American Airlines reviews

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

The professionals have excellent customer service, the seats don´t have enough space.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

Bags took over and hour to come out. Delays due to wind caused rebooking.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports