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Cayman Islands

$315+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
nov. 5 — nov. 121
mié. 11/5
mié. 11/12
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 octubre 6, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$683
(American Airlines)

One-way from

$315
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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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 octubre 6, 2025.

This American Airlines deal was found by Cheapflights users on 10/5. 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.
vie. 11/77:19 amPOS - GCM
1 stop14h 09mAmerican Airlines
vie. 11/149:00 amGCM - POS
1 stop13h 39mAmerican Airlines
Deal found 10/5$683
This Booking.com deal was found by Cheapflights users on 10/5. 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.
jue. 10/236:25 pmPOS - GCM
1 stop18h 10mMultiple Airlines
mié. 10/295:10 pmGCM - POS
2 stops19h 50mMultiple Airlines
Deal found 10/5$705
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
jue. 12/1812:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$714
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/147:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
jue. 12/1812:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$720
This Kiwi.com deal was found by Cheapflights users on 10/3. 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.
vie. 10/249:10 amPOS - GCM
1 stop13h 05mMultiple Airlines
mar. 10/2811:30 amGCM - POS
2 stops24h 47mMultiple Airlines
Deal found 10/3$782
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
sáb. 12/2012:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$827
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
dom. 12/2112:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$832
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/147:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
dom. 12/2112:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$838
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/117:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
vie. 12/1912:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$866
This deal was found by Cheapflights users on 10/5. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/147:10 amPOS - GCM
1 stop8h 34mAmerican Airlines
vie. 12/1912:50 pmGCM - POS
1 stop9h 56mAmerican Airlines
Deal found 10/5$872

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 octubre 6, 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

vie. 10/24

7:00 am-7:20 pm

1 stop13h 20m

George Town Owen Roberts Intl

mar. 10/28

8:25 am-9:20 pm

1 stop11h 55m

$683

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

vie. 11/7

7:19 am-2:46 pm

1 stop8h 27m

George Town Owen Roberts Intl

vie. 11/14

3:36 pm-11:39 pm

1 stop7h 03m

$683

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

jue. 10/23

7:00 am-1:10 pm

1 stop7h 10m

George Town Owen Roberts Intl

mié. 10/29

12:10 pm-9:20 pm

1 stop8h 10m

$683

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

sáb. 12/13

7:10 am-2:44 pm

1 stop8h 34m

George Town Owen Roberts Intl

jue. 12/18

12:50 pm-11:46 pm

1 stop9h 56m

$714

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

vie. 12/12

7:10 am-2:44 pm

1 stop8h 34m

George Town Owen Roberts Intl

jue. 12/18

12:50 pm-11:46 pm

1 stop9h 56m

$714

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

jue. 12/11

7:10 am-2:44 pm

1 stop8h 34m

George Town Owen Roberts Intl

jue. 12/18

12:50 pm-11:46 pm

1 stop9h 56m

$714

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

lun. 12/15

7:10 am-2:44 pm

1 stop8h 34m

George Town Owen Roberts Intl

jue. 12/18

12:50 pm-11:46 pm

1 stop9h 56m

$714

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

vie. 10/24

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

mar. 10/28

11:30 am-1:17 pm

2 stops24h 47m

$782

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

sáb. 12/13

7:10 am-2:44 pm

1 stop8h 34m

George Town Owen Roberts Intl

sáb. 12/20

12:50 pm-11:46 pm

1 stop9h 56m

$827

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

lun. 12/15

7:10 am-2:44 pm

1 stop8h 34m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/5

Showing 1-10 of 13 results
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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 octubre 6, 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
11,040 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Boarding

7.5

Food

6.4

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
11,040 reviews
American Airlines
7.2
Good
11,040 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Entertainment

6.9

Boarding

7.5

Food

6.4

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 13h 20m. 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 octubre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$666Average$722FlexibilityNo cancel feeOn-time71%

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