$687 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 7/10. 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

Fri, Jul 10 - Thu, Jul 16
Southwest Logo
9:20 pm - 10:30 am
PDX
-
GCM
11h 10m
1 stop
Southwest Logo
12:50 pm - 11:55 pm
GCM
-
PDX
13h 05m
2 stops
$687Southwest
Fri, Jul 10 - Thu, Jul 16
Southwest Logo
5:00 pm - 12:10 pm
PDX
-
GCM
17h 10m
2 stops
Southwest Logo
12:50 pm - 12:35 am
GCM
-
PDX
13h 45m
2 stops
$757Southwest
Sat, Sep 5 - Sun, Sep 13
Multiple Airlines Logo
5:42 pm - 4:00 pm
PDX
-
GCM
20h 18m
1 stop
Multiple Airlines Logo
6:10 pm - 9:48 am
GCM
-
PDX
17h 38m
1 stop
$761Multiple Airlines
Sat, Sep 5 - Sun, Sep 13
Multiple Airlines Logo
5:42 pm - 4:00 pm
PDX
-
GCM
20h 18m
1 stop
Multiple Airlines Logo
6:10 pm - 1:37 pm
GCM
-
PDX
21h 27m
2 stops
$764Multiple Airlines
Mon, Jul 27 - Tue, Aug 4
American Airlines Logo
12:45 am - 1:36 pm
PDX
-
GCM
10h 51m
1 stop
American Airlines Logo
12:33 pm - 11:55 pm
GCM
-
PDX
13h 22m
1 stop
$781American Airlines
Mon, Jul 27 - Tue, Aug 4
American Airlines Logo
12:45 am - 1:36 pm
PDX
-
GCM
10h 51m
1 stop
American Airlines Logo
12:02 pm - 10:51 pm
GCM
-
PDX
12h 49m
2 stops
$786American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
12:01 pm - 11:00 am
PDX
-
GCM
20h 59m
2 stops
American Airlines Logo
12:36 pm - 12:07 am
GCM
-
PDX
13h 31m
2 stops
$791American Airlines
Fri, Jul 10 - Thu, Jul 16
American Airlines Logo
9:47 pm - 3:03 pm
PDX
-
GCM
15h 16m
1 stop
American Airlines Logo
2:41 pm - 10:51 pm
GCM
-
PDX
10h 10m
1 stop
$794American Airlines
Fri, Jul 10 - Thu, Jul 16
American Airlines Logo
9:47 pm - 3:03 pm
PDX
-
GCM
15h 16m
1 stop
American Airlines Logo
2:41 pm - 10:51 pm
GCM
-
PDX
10h 10m
1 stop
$804American Airlines
Sun, Aug 16 - Sat, Aug 22
American Airlines Logo
9:44 pm - 11:27 am
PDX
-
GCM
11h 43m
1 stop
American Airlines Logo
4:00 pm - 10:54 am
GCM
-
PDX
20h 54m
2 stops
$812American 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 $415, 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.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$687
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 11% 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 11688 reviews
6.4Food
7.9Crew
6.8Entertainment
7.2Comfort
7.5Boarding
Airline reviews

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

10.0 ExcellentShahid Bobby, Jun 2026
ORF - JFK
Read more American Airlines reviews

Excellent service. Flight attendance like Jessica,, on our flight, is a reason I wouldn’t mind flying through British Airways again. Jessica,, was very courteous and helpful.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

Significant delays on my trip to Chicago and my trip back to NY

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

Delayed by 5 hours and I had to wit in the airport for more than 6+ hours.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

technology worked well and everything ran smoothly. The seats are quite cramped so please don't try to re-engineer the cabin to squeeze more bodies on board.

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

Flight was delayed due to connecting passengers. Lack of snack options bad. Sitting in Aisle, last cart run pulled the cart directly into my knee. Rude awakening.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports

Portland (PDX)