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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
POS — JFK
Dec 26 — Jan 21
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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 November 26, 2025.

Good round-trip deal

$66 or less

Good one-way deal

$35 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 November 26, 2025.

This United Airlines deal was found by Cheapflights users on 11/24. 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.
Mon 12/221:30 amPOS - BOS
2 stops23h 24mUnited Airlines
Tue 1/612:45 pmBOS - POS
2 stops34h 38mUnited Airlines
Deal found 11/24$241
This United Airlines deal was found by Cheapflights users on 11/24. 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.
Wed 12/171:30 amPOS - BOS
2 stops24h 15mUnited Airlines
Thu 1/812:45 pmBOS - POS
2 stops34h 38mUnited Airlines
Deal found 11/24$243
This JetBlue deal was found by Cheapflights users on 11/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1312:22 pmPOS - BOS
1 stop12h 35mJetBlue
Sat 2/216:15 pmBOS - POS
1 stop12h 02mJetBlue
Deal found 11/26$248
This United Airlines deal was found by Cheapflights users on 11/26. 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 amPOS - BOS
2 stops19h 41mUnited Airlines
Sat 2/215:35 amBOS - POS
2 stops17h 48mUnited Airlines
Deal found 11/26$252
This United Airlines deal was found by Cheapflights users on 11/23. 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 1/221:30 amPOS - BOS
1 stop11h 49mUnited Airlines
Sat 1/2412:45 pmBOS - POS
2 stops34h 38mUnited Airlines
Deal found 11/23$271
This Mytrip deal was found by Cheapflights users on 11/24. 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.
Thu 3/127:30 amPOS - GND
Nonstop0h 40mCaribbean Airlines
Mon 3/166:00 amGND - POS
Nonstop0h 40mCaribbean Airlines
Deal found 11/24$274
This Trip.com deal was found by Cheapflights users on 11/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/218:00 amPOS - MCO
1 stop16h 08mJetBlue
Mon 1/266:00 amMCO - POS
1 stop12h 11mJetBlue
Deal found 11/24$275
This United Airlines deal was found by Cheapflights users on 11/24. 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.
Wed 12/171:30 amPOS - BOS
1 stop11h 36mUnited Airlines
Wed 12/316:20 amBOS - POS
1 stop17h 03mUnited Airlines
Deal found 11/24$281
This Mytrip deal was found by Cheapflights users on 11/24. 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 5/19:50 pmPOS - GND
Nonstop0h 40mCaribbean Airlines
Sun 5/38:55 amGND - POS
Nonstop0h 40mCaribbean Airlines
Deal found 11/24$282
This Trip.com deal was found by Cheapflights users on 11/25. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/78:30 amPOS - BOS
1 stop9h 43mJetBlue
Mon 2/165:05 pmBOS - POS
1 stop13h 12mJetBlue
Deal found 11/25$284
This SmartFares deal was found by Cheapflights users on 11/23. 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.
Mon 3/27:30 amPOS - GND
Nonstop0h 40mCaribbean Airlines
Thu 3/58:55 amGND - POS
Nonstop0h 40mCaribbean Airlines
Deal found 11/23$284
This Gotogate deal was found by Cheapflights users on 11/24. 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.
Mon 1/127:30 amPOS - GND
Nonstop0h 40mCaribbean Airlines
Thu 1/151:40 pmGND - POS
Nonstop0h 40mCaribbean Airlines
Deal found 11/24$287

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 November 26, 2025. 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 SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 12/22

1:30 am-11:38 pm

1 stop23h 08m

Boston Logan Intl

Thu 1/8

12:45 pm-12:23 am

2 stops34h 38m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Thu 2/12

1:30 am-11:57 pm

2 stops23h 27m

Boston Logan Intl

Sat 2/21

7:48 am-12:23 am

2 stops15h 35m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Mon 12/22

1:30 am-11:54 pm

2 stops23h 24m

Boston Logan Intl

Wed 1/7

12:45 pm-12:23 am

2 stops34h 38m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 12/20

1:30 am-11:38 pm

1 stop23h 08m

Boston Logan Intl

Wed 1/7

11:42 am-12:23 am

1 stop11h 41m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 12/20

1:30 am-11:38 pm

1 stop23h 08m

Boston Logan Intl

Thu 1/1

6:20 am-12:23 am

1 stop17h 03m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Wed 12/17

1:30 am-11:38 pm

1 stop23h 08m

Boston Logan Intl

Thu 1/8

3:25 pm-12:23 am

1 stop31h 58m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Sat 12/20

1:30 am-9:29 pm

1 stop20h 59m

Boston Logan Intl

Thu 1/8

7:05 am-12:23 am

1 stop16h 18m

$241

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Wed 12/17

1:30 am-12:06 pm

1 stop11h 36m

Boston Logan Intl

Wed 1/7

3:25 pm-12:23 am

1 stop31h 58m

$243

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Wed 12/17

1:30 am-12:06 pm

1 stop11h 36m

Boston Logan Intl

Tue 1/6

12:45 pm-12:23 am

2 stops34h 38m

$243

Port of SpainBoston

POS - BOS

POSBOS

Port of Spain Piarco Intl

Wed 12/17

1:30 am-12:45 am

2 stops24h 15m

Boston Logan Intl

Thu 1/1

6:20 am-12:23 am

1 stop17h 03m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 60 results
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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 $287). 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 November 25, 2025.

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 November 26, 2025. 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.

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Food

6.8

Crew

8.4

Overall

8.0

Boarding

8.1

Entertainment

6.7

Comfort

7.8

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

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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 November 26, 2025.
  • 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 Boston from $284 round trip
    Fly from Port of Spain to Miami from $297 round trip
    Fly from Port of Spain to New York from $345 round trip
    Fly from Port of Spain to Toronto from $470 round trip

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