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Cayman Islands

$350+ Cheap flights from Port of Spain (POS) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Apr 1 — Apr 81
Wed 4/1
Wed 4/8
1 adult, Economy
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Cheap flight deals from Port of Spain to Cayman Islands

Cheapest flights from Port of Spain to Cayman Islands
Explore the most affordable flight options available from Port of Spain to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 2, 2026.

This Gotogate deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:10 am
POS
-
GCM
1 stop13h 05m
Multiple Airlines
Sun 10/187:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 2/27$605
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:00 am
POS
-
GCM
1 stop29h 10m
American Airlines
Fri 8/2812:10 pm
GCM
-
POS
1 stop8h 26m
American Airlines
Deal found 2/27$705
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/213:47 pm
POS
-
GCM
1 stop46h 23m
American Airlines
Tue 4/2812:00 pm
GCM
-
POS
1 stop25h 32m
American Airlines
Deal found 2/27$728
This American Airlines deal was found by Cheapflights users on 2/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/113:47 pm
POS
-
GCM
1 stop20h 13m
American Airlines
Mon 5/1812:00 pm
GCM
-
POS
1 stop49h 32m
American Airlines
Deal found 2/28$736
This American Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:47 pm
POS
-
GCM
1 stop22h 23m
American Airlines
Thu 5/1412:00 pm
GCM
-
POS
1 stop25h 32m
American Airlines
Deal found 2/26$751
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:10 pm
POS
-
GCM
1 stop20h 59m
American Airlines
Sun 4/122:10 pm
GCM
-
POS
1 stop23h 22m
American Airlines
Deal found 2/27$757
This American Airlines deal was found by Cheapflights users on 2/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:47 pm
POS
-
GCM
1 stop20h 08m
American Airlines
Thu 5/2112:02 pm
GCM
-
POS
1 stop9h 57m
American Airlines
Deal found 2/26$761
This American Airlines deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:10 pm
POS
-
GCM
1 stop29h 05m
American Airlines
Sat 4/1111:55 am
GCM
-
POS
1 stop25h 37m
American Airlines
Deal found 2/27$819
This Kiwi.com deal was found by Cheapflights users on 2/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/19:10 am
POS
-
GCM
1 stop7h 55m
Multiple Airlines
Sun 4/121:52 pm
GCM
-
POS
1 stop29h 08m
Multiple Airlines
Deal found 2/27$858

Find flight deals from Port of Spain to Cayman Islands

Keep the following information in mind while searching for Port of Spain to Cayman Islands flight deals. Data was last updated March 2, 2026.

Round-trip from

$705
(American Airlines)

One-way from

$350
(American Airlines)
From Port of Spain Piarco Intl to Cayman Islands
Search Deals
One-way flight from Port of Spain Piarco Intl to Cayman Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Port of Spain to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 2, 2026.
Use the filters below to find and compare flights from Port of Spain to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 8/21

7:00 am-11:10 am

1 stop29h 10m

George Town Owen Roberts Intl

Fri 8/28

12:10 pm-9:36 pm

1 stop8h 26m

$705

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 5/11

3:47 pm-11:00 am

1 stop20h 13m

George Town Owen Roberts Intl

Mon 5/18

12:00 pm-2:32 pm

1 stop49h 32m

$728

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/8

3:47 pm-1:10 pm

1 stop22h 23m

George Town Owen Roberts Intl

Thu 5/14

12:00 pm-2:32 pm

1 stop25h 32m

$751

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/15

3:47 pm-10:55 am

1 stop20h 08m

George Town Owen Roberts Intl

Thu 5/21

12:02 pm-10:59 pm

1 stop9h 57m

$761

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 4/21

3:47 pm-11:31 am

2 stops20h 44m

George Town Owen Roberts Intl

Tue 4/28

12:00 pm-2:32 pm

1 stop25h 32m

$887

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 5/18

3:47 pm-11:00 am

1 stop20h 13m

$350

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 5/18

9:55 pm-10:25 am

3 stops37h 30m

$720

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/27

Sorted by cheapest first

Best time to book a flight from Port of Spain to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Port of Spain with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Port of Spain to the Cayman Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated March 2, 2026.
Read through reviews of airlines operating flights from Port of Spain to the Cayman Islands, such as American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,369 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.1
Good
11,369 reviews
American Airlines
7.1
Good
11,369 reviews

Comfort

7.2

Crew

8.0

Entertainment

6.9

Food

6.4

Overall

7.1

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Port of Spain to Cayman Islands?

    Most people fly from Port of Spain Piarco Intl (POS) if they book a flight from Port of Spain to Cayman Islands. Port of Spain Piarco Intl is conveniently located just 12.6 mi from Port of Spain’s city center.

  • How long is the flight from Port of Spain to Cayman Islands?

    American Airlines can get you from Port of Spain to Cayman Islands in just under 29h 10m. Your travel time can differ by up to . Port of Spain and Cayman Islands are separated by a distance of 1463 mi.

  • Can I find deals for flights from Port of Spain to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Port of Spain to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Port of Spain to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Port of Spain to Cayman Islands.

  • Can I find deals for business class flights from Port of Spain to Cayman Islands?

    Yes. Cheapflights offers flight deals from Port of Spain to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Port of Spain to Cayman Islands

Discover the top airline that operate flights from Port of Spain to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$757FlexibilityNo cancel feeOn-time71%

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