$218 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 6/2. 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
Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Thu, Jun 4 - Mon, Jun 8
Air Canada Logo
7:45 pm - 10:00 am
PDX
-
GCM
36h 15m
2 stops
Air Canada Logo
12:25 pm - 9:30 am
GCM
-
PDX
23h 05m
2 stops
$646Air Canada
Wed, Jun 24 - Thu, Jul 2
Southwest Logo
7:50 pm - 11:50 am
PDX
-
GCM
14h 00m
2 stops
Southwest Logo
12:45 pm - 12:30 am
GCM
-
PDX
13h 45m
2 stops
$682Southwest
Fri, May 15 - Fri, May 22
Southwest Logo
2:50 pm - 12:05 pm
PDX
-
GCM
19h 15m
2 stops
Southwest Logo
1:05 pm - 12:10 am
GCM
-
PDX
13h 05m
2 stops
$687Southwest
Tue, Jul 21 - Sun, Jul 26
Southwest Logo
9:20 pm - 11:50 am
PDX
-
GCM
12h 30m
2 stops
Southwest Logo
12:45 pm - 12:05 am
GCM
-
PDX
13h 20m
2 stops
$707Southwest
Sat, Aug 1 - Sat, Aug 8
Air Canada Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Air Canada Logo
10:40 am - 7:11 pm
GCM
-
PDX
34h 31m
2 stops
$715Air Canada
Fri, Jul 24 - Sat, Aug 1
WestJet Logo
2:30 pm - 12:45 pm
PDX
-
GCM
20h 15m
2 stops
WestJet Logo
1:45 pm - 1:50 pm
GCM
-
PDX
26h 05m
3 stops
$721WestJet
Fri, Jul 24 - Sat, Aug 1
WestJet Logo
2:30 pm - 12:45 pm
PDX
-
GCM
20h 15m
2 stops
WestJet Logo
1:45 pm - 1:50 pm
GCM
-
PDX
26h 05m
2 stops
$725WestJet
Sun, Jul 12 - Sat, Jul 18
Southwest Logo
7:25 pm - 11:50 am
PDX
-
GCM
14h 25m
2 stops
Southwest Logo
11:30 am - 11:55 pm
GCM
-
PDX
14h 25m
2 stops
$727Southwest
Fri, Oct 16 - Sun, Oct 25
Air Canada Logo
7:45 pm - 11:30 am
PDX
-
GCM
13h 45m
2 stops
Air Canada Logo
12:15 pm - 6:30 pm
GCM
-
PDX
32h 15m
2 stops
$734Air Canada
Sat, Aug 1 - Sat, Aug 8
Multiple Airlines Logo
7:45 pm - 11:25 am
PDX
-
GCM
37h 40m
2 stops
Multiple Airlines Logo
8:30 am - 8:50 pm
GCM
-
PDX
14h 20m
1 stop
$754Multiple 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 $398, 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 $1,230 and $991 respectively.

Good to know

Low seasonJanuary
Cheapest flight$218
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 10% 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 11659 reviews
6.9Entertainment
7.9Crew
7.2Comfort
6.4Food
7.5Boarding
Airline reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

2.0 MediocreStella, Apr 2026
ORD - DCA
Read more American Airlines reviews

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

As we approached Denver, we encountered quite a bit of turbulence. I know this can sometimes be the case as I frequently fly this route but not on American. My gripe: Usually a pilot or co-pilot alerts passengers to the possibility of turbulance ahead of time. This did not occur nor did he communiucate during what was a pretty rough ride.

The staff was nice. I appreciated that I was able to take an earlier flight, even though it was last minute. The boarding process felt rather chaotic.

Overall a good experience, however Wifi was not working on the flight.

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

Airlines should be prohibited from using the seats they get away with.

My flight got delayed a total of five times. And the boarding gate changed four times. most of the time the platform was not up-to-date with the changes taking place. The most discouraging part of the entire trip by far.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports