Trinidad and Tobago

$148+ Cheap flights from Trinidad and Tobago

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 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
POS — JFK
Feb 15 — Feb 221
We work with more than 300 partners to bring you better travel deals

What to know about flights from Trinidad and Tobago

Discover essential information about flights departing from Trinidad and Tobago, including flight schedules, destinations, airlines operating at the Trinidad and Tobago airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated January 16, 2026.

Good round-trip deal

$62 or less

Good one-way deal

$37 or less
Price to beat on a round-trip flight from Trinidad and Tobago.
Price to beat on a one-way flight from Trinidad and Tobago.

Find flights from Trinidad and Tobago

Cheapest flights from Trinidad and Tobago
Explore the most affordable flight options available from Trinidad and Tobago. Find the lowest fares based on data from user searches, with prices last updated on January 16, 2026.

This Copa Airlines deal was found by Cheapflights users on 1/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/282:28 pm
POS
-
MCO
1 stop8h 40m
Copa Airlines
Sat 3/74:01 pm
MCO
-
POS
1 stop8h 45m
Copa Airlines
Deal found 1/14$257
This Expedia deal was found by Cheapflights users on 1/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/138:50 am
POS
-
BOS
1 stop12h 13m
JetBlue
Sat 2/216:15 pm
BOS
-
POS
1 stop12h 02m
JetBlue
Deal found 1/13$264
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/101:30 am
POS
-
BOS
2 stops14h 00m
United Airlines
Thu 2/197:15 am
BOS
-
POS
1 stop16h 08m
United Airlines
Deal found 1/14$266
This United Airlines deal was found by Cheapflights users on 1/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:30 am
POS
-
BOS
1 stop11h 46m
United Airlines
Tue 5/121:30 pm
BOS
-
POS
1 stop33h 53m
United Airlines
Deal found 1/15$267
This Mytrip deal was found by Cheapflights users on 1/15. 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.
Tue 2/247:30 am
POS
-
GND
Nonstop0h 40m
Caribbean Airlines
Tue 3/38:55 am
GND
-
POS
Nonstop0h 40m
Caribbean Airlines
Deal found 1/15$271
This Copa Airlines deal was found by Cheapflights users on 1/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:28 pm
POS
-
MCO
1 stop8h 40m
Copa Airlines
Fri 3/61:43 pm
MCO
-
POS
1 stop11h 03m
Copa Airlines
Deal found 1/14$275
This United Airlines deal was found by Cheapflights users on 1/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/121:30 am
POS
-
BOS
2 stops21h 31m
United Airlines
Sat 2/217:48 am
BOS
-
POS
2 stops15h 35m
United Airlines
Deal found 1/14$276
This Booking.com deal was found by Cheapflights users on 1/13. 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.
Thu 3/197:30 am
POS
-
GND
Nonstop0h 40m
Caribbean Airlines
Mon 3/236:00 am
GND
-
POS
Nonstop0h 40m
Caribbean Airlines
Deal found 1/13$281
This Booking.com deal was found by Cheapflights users on 1/14. 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 3/159:05 pm
POS
-
GND
Nonstop0h 40m
Caribbean Airlines
Fri 3/208:55 am
GND
-
POS
Nonstop0h 40m
Caribbean Airlines
Deal found 1/14$283
This Gotogate deal was found by Cheapflights users on 1/14. 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 2/69:50 pm
POS
-
GND
Nonstop0h 40m
Caribbean Airlines
Tue 2/108:55 am
GND
-
POS
Nonstop0h 40m
Caribbean Airlines
Deal found 1/14$284
This SmartFares deal was found by Cheapflights users on 1/15. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/307:30 am
POS
-
GND
Nonstop0h 40m
Caribbean Airlines
Sat 2/75:50 am
GND
-
POS
Nonstop0h 40m
Caribbean Airlines
Deal found 1/15$289
This American Airlines deal was found by Cheapflights users on 1/16. 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.
Sat 2/74:30 pm
POS
-
BOS
2 stops19h 00m
American Airlines
Sat 2/215:30 pm
BOS
-
POS
2 stops20h 36m
American Airlines
Deal found 1/16$292

Find flights from Trinidad and Tobago within your budget

 
Find flights departing from Trinidad and Tobago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on January 16, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

John F Kennedy Intl

Route

Depart

Return

Price

Port of SpainOrlando

POS - MCO

POSMCO

Port of Spain Piarco Intl

Sat 2/28

2:28 pm-10:08 pm

1 stop8h 40m

Orlando

Sat 3/7

4:01 pm-1:46 am

1 stop8h 45m

$257

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/13

8:50 am-8:03 pm

1 stop12h 13m

Boston Logan Intl

Sat 2/21

6:15 pm-7:17 am

1 stop12h 02m

$264

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 5/8

12:30 am-9:33 pm

2 stops21h 03m

Boston Logan Intl

Wed 5/13

9:30 am-11:23 pm

2 stops13h 53m

$266

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 2/12

1:30 am-11:30 pm

1 stop23h 00m

Boston Logan Intl

Sat 2/21

7:19 pm-12:23 am

2 stops28h 04m

$266

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/6

1:30 am-6:20 pm

1 stop17h 50m

Boston Logan Intl

Wed 3/11

9:32 am-11:23 pm

1 stop13h 51m

$266

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Fri 2/13

1:30 am-9:31 pm

1 stop21h 01m

Boston Logan Intl

Sat 2/28

9:47 am-12:23 am

1 stop13h 36m

$266

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Tue 2/10

1:30 am-12:19 pm

1 stop11h 49m

Boston Logan Intl

Thu 2/19

7:15 am-12:23 am

1 stop16h 08m

$266

Port of SpainSt. George's

POS - GND

POSGND

Port of Spain Piarco Intl

Tue 2/24

7:30 am-8:10 am

Nonstop0h 40m

St. George's Point Saline Intl

Tue 3/3

8:55 am-9:35 am

Nonstop0h 40m

$271

Port of SpainOrlando

POS - MCO

POSMCO

Port of Spain Piarco Intl

Mon 4/13

3:44 am-2:17 pm

1 stop10h 33m

Orlando

Fri 4/17

5:00 pm-1:40 am

1 stop8h 40m

$275

Port of SpainOrlando

POS - MCO

POSMCO

Port of Spain Piarco Intl

Fri 2/27

2:16 pm-10:08 pm

1 stop8h 52m

Orlando

Fri 3/6

4:01 pm-1:46 am

1 stop8h 45m

$275

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly 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.

Travel insights for flights from Trinidad and Tobago

Get recent, data-driven insights about flights from Trinidad and Tobago including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Trinidad and Tobago?

Currently, March is the cheapest month in which you can book a flight from Trinidad and Tobago (average of $176). Flying from Trinidad and Tobago in October will prove the most costly (average of $286). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Trinidad and Tobago?

Use this chart to determine the cheapest time to fly round-trip from Trinidad and Tobago to John F Kennedy Intl. Price data was last updated on January 10, 2026.

Those who are seeking the cheapest fare on flights departing from Trinidad and Tobago would be wise to consider leaving during Saturday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Monday at noon when fares are usually the most expensive.

Airline reviews for flights from Trinidad and Tobago

Read reviews and ratings of airlines operating flights from Trinidad and Tobago. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Trinidad and Tobago travel. Please note that the reviews are sourced from user searches and were last updated on January 16, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Peruse reviews from past customers who have flown Caribbean Airlines, Copa Airlines, and American Airlines from Trinidad and Tobago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Boarding

7.9

Crew

8.3

Comfort

7.8

Entertainment

6.6

Food

6.7

Overall

7.9

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Caribbean regions

Book your next flight out of one of these popular departure points located in Caribbean.

Related info for your journey

Access useful and relevant information related to your journey from Trinidad and Tobago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated January 16, 2026.
  • What is the cheapest month to fly from Trinidad and Tobago?

    March is currently the cheapest month to fly from Trinidad and Tobago. At this moment in time October is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Trinidad and Tobago?

    Check out the cheapest flights from Trinidad and Tobago to embark to:
    Fly from Port of Spain to Orlando from $257 round trip
    Fly from Port of Spain to Miami from $291 round trip
    Fly from Port of Spain to New York from $331 round trip
    Fly from Port of Spain to Toronto from $524 round trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.