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Cayman Islands

$528+ Cheap flights from Port of Spain (POS) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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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 January 8, 2026.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$528
(Gotogate)
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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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 January 8, 2026.

This Gotogate deal was found by Cheapflights users on 1/6. 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.
Fri 4/249:10 amPOS - GCM
2 stops30h 40mMultiple Airlines
Mon 4/277:00 amGCM - POS
1 stop10h 55mMultiple Airlines
Deal found 1/6$528
This Gotogate deal was found by Cheapflights users on 1/6. 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.
Tue 2/109:10 amPOS - GCM
1 stop7h 55mMultiple Airlines
Fri 2/204:45 pmGCM - POS
1 stop25h 10mMultiple Airlines
Deal found 1/6$569
This American Airlines deal was found by Cheapflights users on 1/7. 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 1/156:30 amPOS - GCM
1 stop9h 15mAmerican Airlines
Wed 1/218:50 amGCM - POS
1 stop12h 58mAmerican Airlines
Deal found 1/7$652
This American Airlines deal was found by Cheapflights users on 1/7. 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 pmPOS - GCM
1 stop22h 24mAmerican Airlines
Mon 5/1812:00 pmGCM - POS
1 stop49h 32mAmerican Airlines
Deal found 1/7$692
This Gotogate deal was found by Cheapflights users on 1/7. 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 1/159:10 amPOS - GCM
1 stop13h 05mMultiple Airlines
Wed 1/215:10 pmGCM - POS
2 stops19h 45mMultiple Airlines
Deal found 1/7$704
This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/169:10 amPOS - GCM
2 stops30h 40mMultiple Airlines
Wed 1/215:10 pmGCM - POS
2 stops19h 45mMultiple Airlines
Deal found 1/7$707
This American Airlines deal was found by Cheapflights users on 1/6. 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 pmPOS - GCM
1 stop22h 24mAmerican Airlines
Tue 4/282:10 pmGCM - POS
1 stop23h 22mAmerican Airlines
Deal found 1/6$718
This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/249:10 amPOS - GCM
2 stops30h 40mMultiple Airlines
Tue 4/281:45 pmGCM - POS
1 stop13h 55mMultiple Airlines
Deal found 1/7$797

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 January 8, 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

Port of Spain

Fly to

Cayman Islands

Route

Depart

Return

Price

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 4/24

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

Mon 4/27

7:00 am-6:55 pm

1 stop10h 55m

$530

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

$692

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Tue 4/21

3:47 pm-1:11 pm

1 stop22h 24m

George Town Owen Roberts Intl

Tue 4/28

2:10 pm-2:32 pm

1 stop23h 22m

$718

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/8

3:47 pm-10:55 am

1 stop20h 08m

George Town Owen Roberts Intl

Thu 5/14

2:10 pm-2:32 pm

1 stop23h 22m

$718

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 4/24

9:10 am-2:50 pm

2 stops30h 40m

George Town Owen Roberts Intl

Tue 4/28

1:45 pm-4:40 am

1 stop13h 55m

$797

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

Fri 2/20

4:45 pm-1:33 pm

2 stops19h 48m

$840

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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 January 8, 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
7.2
Good
11,094 reviews

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

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
11,094 reviews
American Airlines
7.2
Good
11,094 reviews

Comfort

7.2

Boarding

7.5

Overall

7.2

Entertainment

6.9

Food

6.4

Crew

8.0

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 20h 13m. 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$757FlexibilityNo cancel feeOn-time71%

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