$250 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 1/28. 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

Sun, Jan 11 - Thu, Jan 15
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 9:15 am
GCM
-
PDX
22h 45m2 stops
$552Air Canada
Sun, Jan 11 - Thu, Jan 15
Southwest Logo
4:15 pm - 12:55 pm
PDX
-
GCM
17h 40m2 stops
Southwest Logo
1:50 pm - 10:30 pm
GCM
-
PDX
11h 40m2 stops
$565Southwest
Sun, Jan 11 - Thu, Jan 15
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m2 stops
$581Air Canada
Sun, Jan 11 - Thu, Jan 15
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
38h 25m2 stops
Air Canada Logo
1:30 pm - 2:40 pm
GCM
-
PDX
28h 10m2 stops
$591Air Canada
Sun, Jan 11 - Thu, Jan 15
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
25h 35m1 stop
Multiple Airlines Logo
1:30 pm - 6:30 pm
GCM
-
PDX
32h 00m2 stops
$639Multiple Airlines
Mon, Jan 26 - Tue, Feb 3
KLM Logo
5:25 pm - 12:40 pm
PDX
-
GCM
16h 15m2 stops
KLM Logo
2:05 pm - 10:15 pm
GCM
-
PDX
11h 10m1 stop
$654KLM
Sun, Jan 11 - Thu, Jan 15
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
25h 35m1 stop
Multiple Airlines Logo
4:45 pm - 8:27 pm
GCM
-
PDX
30h 42m1 stop
$656Multiple Airlines
Mon, Jan 26 - Tue, Feb 3
American Airlines Logo
11:01 pm - 12:05 pm
PDX
-
GCM
10h 04m1 stop
American Airlines Logo
3:45 pm - 11:46 pm
GCM
-
PDX
11h 01m1 stop
$659American Airlines
Fri, Jan 23 - Sat, Jan 31
American Airlines Logo
11:01 pm - 8:20 pm
PDX
-
GCM
18h 19m1 stop
American Airlines Logo
3:45 pm - 11:46 pm
GCM
-
PDX
11h 01m1 stop
$666American Airlines
Fri, Jan 23 - Sat, Jan 31
American Airlines Logo
11:01 pm - 8:20 pm
PDX
-
GCM
18h 19m1 stop
American Airlines Logo
8:50 am - 8:17 pm
GCM
-
PDX
14h 27m2 stops
$671American 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 $365, 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 December, when the average cost of round-trip tickets is $1,142 and $1,077 respectively.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$250
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 1% 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.

  • What is the cheapest time of day to fly to Grand Cayman?

    The cheapest time of day to fly to Grand Cayman is generally in the evening, when round-trip flights cost $557 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Grand Cayman is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $833.

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 11056 reviews
7.5Boarding
6.9Entertainment
6.4Food
7.2Comfort
8.0Crew
Airline reviews

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

10.0 ExcellentPaul, Dec 2025
SEA - CLT
Read more American Airlines reviews

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was delayed 17 hours due to aircraft issues. American did provide hotel, transportation and meals, 3 hours past boarding time, but it took us another hour to get the vouchers.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Portland (PDX)