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Cayman Islands

$305+ 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 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find 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 November 20, 2025.

This Gotogate deal was found by Cheapflights users on 11/17. 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 11/279:10 amPOS - GCM
1 stop13h 05mMultiple Airlines
Thu 12/117:00 amGCM - POS
1 stop10h 55mMultiple Airlines
Deal found 11/17$666
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 11/277:19 amPOS - GCM
1 stop14h 09mAmerican Airlines
Thu 12/111:25 pmGCM - POS
1 stop9h 34mAmerican Airlines
Deal found 11/18$669
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/14:30 pmPOS - GCM
2 stops20h 27mAmerican Airlines
Fri 12/53:45 pmGCM - POS
1 stop7h 14mAmerican Airlines
Deal found 11/20$823
This Booking.com deal was found by Cheapflights users on 11/20. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/3012:10 amPOS - GCM
1 stop14h 50mMultiple Airlines
Fri 12/57:00 amGCM - POS
1 stop10h 55mMultiple Airlines
Deal found 11/20$1,326

Cheap 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 November 20, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$596
(Booking.com)

One-way from

$305
(Mytrip)
Provider with most accurate pricing for Port of Spain Piarco Intl-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-George Town Owen Roberts Intl flights.
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From Port of Spain Piarco Intl to Cayman Islands
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One-way flight from Port of Spain Piarco Intl to Cayman Islands
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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 November 20, 2025.
Use the filters below to find and compare flights from Port of Spain to the Cayman Islands that are best for you.

Fly from

Port of Spain

Fly to

Cayman Islands

Route

Depart

Return

Price

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 1/29

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

Mon 2/2

7:00 am-6:55 pm

1 stop10h 55m

$596

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 2/10

9:10 am-4:05 pm

1 stop7h 55m

George Town Owen Roberts Intl

Mon 2/16

4:45 pm-6:55 pm

1 stop25h 10m

$618

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 12/1

7:19 am-8:28 pm

1 stop14h 09m

George Town Owen Roberts Intl

Fri 12/5

3:45 pm-11:59 pm

1 stop7h 14m

$669

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 2/2

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

Sat 2/7

8:50 am-6:55 pm

1 stop9h 05m

$798

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 1/29

4:30 pm-11:26 am

2 stops19h 56m

George Town Owen Roberts Intl

Mon 2/2

8:50 am-10:48 pm

1 stop12h 58m

$823

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Mon 2/2

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

Fri 2/6

4:45 pm-6:55 pm

1 stop25h 10m

$847

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 2/10

4:30 pm-11:26 am

2 stops19h 56m

George Town Owen Roberts Intl

Mon 2/16

12:54 pm-3:30 pm

1 stop25h 36m

$869

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 11/27

9:10 am-9:15 pm

1 stop13h 05m

$305

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Wed 11/26

1:30 am-4:30 pm

1 stop16h 00m

$1,128

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

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 November 20, 2025.
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
7.2
Good
11,047 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.2

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
7.2
Good
11,047 reviews
American Airlines
7.2
Good
11,047 reviews

Comfort

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

Boarding

7.5

Overall

7.2

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 14h 09m. 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 November 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$737FlexibilityNo cancel feeOn-time71%

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