$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
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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

Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m1 stop
Multiple Airlines Logo
4:45 pm - 8:27 pm
GCM
-
PDX
30h 42m1 stop
$529Multiple Airlines
Mon, Jan 26 - Mon, Feb 2
Air Canada Logo
7:00 pm - 12:25 pm
PDX
-
GCM
14h 25m2 stops
Air Canada Logo
1:30 pm - 2:40 pm
GCM
-
PDX
28h 10m2 stops
$533Air Canada
Sun, Jan 18 - Thu, Jan 22
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
$552Air 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 - 6:30 pm
GCM
-
PDX
32h 00m2 stops
$571Air Canada
Mon, Jan 26 - Mon, Feb 2
Multiple Airlines Logo
7:00 am - 4:05 pm
PDX
-
GCM
30h 05m1 stop
Multiple Airlines Logo
1:30 pm - 2:40 pm
GCM
-
PDX
28h 10m2 stops
$580Multiple Airlines
Wed, Apr 22 - Sat, May 2
Air Canada Logo
9:50 am - 11:10 am
PDX
-
GCM
23h 20m2 stops
Air Canada Logo
12:25 pm - 9:30 am
GCM
-
PDX
23h 05m2 stops
$583Air Canada
Wed, Jan 21 - Sun, Jan 25
United Airlines Logo
3:50 pm - 1:45 pm
PDX
-
GCM
18h 55m2 stops
United Airlines Logo
2:50 pm - 10:32 pm
GCM
-
PDX
10h 42m1 stop
$666United Airlines
Fri, Jan 23 - Sat, Jan 31
American Airlines Logo
10:15 pm - 2:45 pm
PDX
-
GCM
13h 30m2 stops
American Airlines Logo
8:50 am - 10:11 pm
GCM
-
PDX
16h 21m2 stops
$671American Airlines
Wed, Feb 25 - Sun, Mar 1
American Airlines Logo
9:44 pm - 2:45 pm
PDX
-
GCM
14h 01m2 stops
American Airlines Logo
3:45 pm - 11:50 pm
GCM
-
PDX
11h 05m1 stop
$676American Airlines
Sun, Jan 18 - Thu, Jan 22
United Airlines Logo
11:05 pm - 1:15 pm
PDX
-
GCM
11h 10m1 stop
United Airlines Logo
2:50 pm - 10:32 pm
GCM
-
PDX
10h 42m1 stop
$776United 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 $362, 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.

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.

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 11073 reviews
6.4Food
6.9Entertainment
7.2Comfort
8.0Crew
7.5Boarding
Airline reviews

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

8.0 ExcellentAnonymous, Dec 2025
ANC - DFW
Read more American Airlines reviews

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

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.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports