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Cayman Islands

$558+ Cheap flights from Trinidad and Tobago 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
POS — GCM
Jun 10 — Jun 171
Wed 6/10
Wed 6/17
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Cayman Islands

Cheapest flights from Trinidad and Tobago to Cayman Islands
Explore the most affordable flight options available from Trinidad and Tobago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 11, 2026.

This Booking.com deal was found by Cheapflights users on 5/7. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:10 am
POS
-
GCM
1 stop13h 25m
Multiple Airlines
Thu 6/44:45 pm
GCM
-
POS
1 stop25h 10m
Multiple Airlines
Deal found 5/7$558
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:10 am
POS
-
GCM
1 stop13h 25m
Multiple Airlines
Sat 5/308:50 am
GCM
-
POS
1 stop9h 05m
Multiple Airlines
Deal found 5/7$626
This Priceline deal was found by Cheapflights users on 5/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/299:10 am
POS
-
GCM
2 stops30h 40m
Multiple Airlines
Mon 6/17:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 5/7$647
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/279:10 am
POS
-
GCM
1 stop27h 25m
Multiple Airlines
Sat 5/308:50 am
GCM
-
POS
1 stop9h 05m
Multiple Airlines
Deal found 5/7$674
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:10 am
POS
-
GCM
1 stop7h 55m
Multiple Airlines
Thu 6/47:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 5/7$700
This American Airlines deal was found by Cheapflights users on 5/7. 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 5/287:00 am
POS
-
GCM
1 stop10h 11m
American Airlines
Fri 5/2912:01 pm
GCM
-
POS
1 stop9h 58m
American Airlines
Deal found 5/7$705
This Gotogate deal was found by Cheapflights users on 5/7. 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 8/69:10 am
POS
-
GCM
1 stop13h 05m
Multiple Airlines
Mon 8/107:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 5/7$708
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Wed 5/277:00 am
POS
-
GCM
1 stop10h 11m
American Airlines
Fri 5/2912:01 pm
GCM
-
POS
1 stop9h 58m
American Airlines
Deal found 5/7$711
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/19:10 am
POS
-
GCM
1 stop13h 05m
Multiple Airlines
Thu 6/47:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 5/7$717
This Kiwi.com deal was found by Cheapflights users on 5/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/29:10 am
POS
-
GCM
1 stop7h 55m
Multiple Airlines
Fri 6/57:00 am
GCM
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 5/7$722

Find flight deals from Trinidad and Tobago to Cayman Islands

Keep the following information in mind while searching for Trinidad and Tobago to Cayman Islands flight deals. Data was last updated May 11, 2026.

Round-trip from

$558
(Booking.com)
From Trinidad and Tobago to Cayman Islands
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago 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 May 11, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Wed 5/27

9:10 am-11:35 am

1 stop27h 25m

George Town Owen Roberts Intl

Sat 5/30

8:50 am-6:55 pm

1 stop9h 05m

$674

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 8/6

9:10 am-9:15 pm

1 stop13h 05m

George Town Owen Roberts Intl

Mon 8/10

7:00 am-6:55 pm

1 stop10h 55m

$708

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/29

9:10 am-2:50 pm

2 stops30h 40m

George Town Owen Roberts Intl

Thu 6/4

2:05 pm-2:21 pm

2 stops23h 16m

$817

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 8/6

7:00 am-11:30 am

2 stops29h 30m

George Town Owen Roberts Intl

Mon 8/10

2:10 pm-11:18 pm

1 stop8h 08m

$989

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/29

9:10 am-9:35 pm

1 stop13h 25m

George Town Owen Roberts Intl

Tue 6/2

11:30 am-8:35 pm

3 stops32h 05m

$1,033
Quickest round-trip

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/29

12:15 pm-8:55 pm

2 stops9h 40m

George Town Owen Roberts Intl

Sun 5/31

7:00 am-6:55 pm

1 stop10h 55m

$1,262

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Thu 5/28

12:30 am-12:35 pm

2 stops37h 05m

George Town Owen Roberts Intl

Sat 5/30

4:15 pm-11:23 pm

2 stops30h 08m

$1,506

Port of SpainGeorge Town

POS - GCM

POSGCM

Port of Spain Piarco Intl

Fri 5/29

12:30 am-12:30 pm

1 stop13h 00m

George Town Owen Roberts Intl

Sat 5/30

4:45 pm-11:23 pm

1 stop29h 38m

$2,012

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/7

Sorted by cheapest first

Best time to book a flight from Trinidad and Tobago to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Trinidad and Tobago 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 Trinidad and Tobago to the Cayman Islands
No data available for this route at this time. Please check back soon.

Related info for your journey

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

  • Can I find deals for flights from Trinidad and Tobago to Cayman Islands that include hotel bookings?

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

  • How can I find direct flights from Trinidad and Tobago to Cayman Islands?

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

  • Can I find deals for business class flights from Trinidad and Tobago to Cayman Islands?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago 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.

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