$135 Find Cheap Flights from Boston to Trinidad and Tobago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Trinidad and Tobago departing on 5/20. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Boston to Trinidad and Tobago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Port of Spain
Port of Spain1 stop$335
Scarborough
Scarborough2 stops$485
Port of Spain
Port of Spain1 stop$335
Scarborough
Scarborough2 stops$485

Book Cheap Boston to Trinidad and Tobago Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Trinidad and Tobago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Trinidad and Tobago

Sun, May 17 - Wed, May 20
American Airlines Logo
5:00 am - 2:32 pm
BOS
-
POS
9h 32m
1 stop
American Airlines Logo
3:47 pm - 12:59 am
POS
-
BOS
9h 12m
1 stop
$335American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
8:19 am - 10:59 pm
BOS
-
POS
14h 40m
2 stops
American Airlines Logo
7:00 am - 9:24 pm
POS
-
BOS
14h 24m
2 stops
$339American Airlines
Mon, Jun 1 - Thu, Jun 4
American Airlines Logo
6:00 am - 10:59 pm
BOS
-
POS
16h 59m
1 stop
American Airlines Logo
3:13 pm - 12:59 am
POS
-
BOS
9h 46m
1 stop
$346American Airlines
Fri, Jun 5 - Mon, Jun 15
American Airlines Logo
5:01 am - 2:11 pm
BOS
-
POS
9h 10m
1 stop
American Airlines Logo
7:01 am - 10:35 pm
POS
-
BOS
15h 34m
2 stops
$350American Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
6:53 pm - 2:32 pm
BOS
-
POS
19h 39m
2 stops
American Airlines Logo
3:47 pm - 11:12 am
POS
-
BOS
19h 25m
2 stops
$369American Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
2:00 pm - 10:59 pm
BOS
-
POS
8h 59m
1 stop
American Airlines Logo
7:00 am - 10:16 pm
POS
-
BOS
15h 16m
1 stop
$371American Airlines
Sun, May 10 - Wed, Jun 3
American Airlines Logo
12:44 pm - 2:32 pm
BOS
-
POS
25h 48m
1 stop
American Airlines Logo
3:12 pm - 12:59 am
POS
-
BOS
9h 47m
1 stop
$374American Airlines
Sat, May 23 - Sat, May 30
American Airlines Logo
11:22 am - 10:59 pm
BOS
-
POS
11h 37m
2 stops
American Airlines Logo
7:00 am - 10:16 pm
POS
-
BOS
15h 16m
1 stop
$375American Airlines
Fri, Jun 12 - Fri, Jun 19
Multiple Airlines Logo
5:10 am - 8:30 am
BOS
-
TAB
27h 20m
2 stops
Multiple Airlines Logo
6:00 pm - 6:22 pm
TAB
-
BOS
24h 22m
2 stops
$485Multiple Airlines
Fri, Jun 12 - Fri, Jun 19
Multiple Airlines Logo
10:45 am - 11:40 am
BOS
-
TAB
24h 55m
2 stops
Multiple Airlines Logo
7:10 pm - 2:41 pm
TAB
-
BOS
19h 31m
3 stops
$517Multiple Airlines
Booking Insights

KAYAK's insights & trends for Boston to Trinidad and Tobago flights

Get data-powered insights and trends into flights from Boston to Trinidad and Tobago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Boston to Trinidad and Tobago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Trinidad and Tobago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Trinidad and Tobago is July, when tickets cost $47 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $477 and $401 respectively.

How far in advance should I book a flight from Boston to Trinidad and Tobago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Trinidad and Tobago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Trinidad and Tobago, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$135
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Boston to Port of Spain

FAQs - booking Trinidad and Tobago flights

  • How can I make my trip from Boston to Trinidad and Tobago more sustainable?

    The airline on which you choose to fly considerably impacts the sustainability of your travels. For example, Air Canada is a pioneer of e-freight, an industry-wide initiative in which the many departments of air travel, including carriers, ground handlers, shippers, and others, replace paper documents with electronic messages. Once fully adopted, e-freight can save an estimated 7800 tons of paper document waste yearly.

  • Where will I have a layover when I fly between Boston and Trinidad and Tobago?

    Flights to Trinidad’s Piarco International Airport typically have layovers at Miami International Airport (MIA) or John F. Kennedy International Airport (JFK), hubs for international travel. Flights might also layover at Charlotte Douglas International Airport (CLT), American Airlines’ second-largest hub. Flights to Tobago’s ANR Robinson International Airport (TAB) typically stop at Toronto Pearson International Airport (YYZ) and Piarco International Airport.

  • What do I need to enter Trinidad and Tobago from the U.S.?

    Travelers entering Trinidad and Tobago should bring their valid U.S. passport, which does not expire during their stay and is good for six months beyond their departure date. Travelers only need a visa to visit Trinidad and Tobago if they plan to stay beyond 90 days.

  • How many carry-on bags can I take when flying from Boston to Trinidad and Tobago?

    Many airlines, including American Airlines, JetBlue, United, Air Canada, British Airways, and Caribbean Airlines, allow passengers to bring one carry-on bag and one personal item within their introductory economy class. However, check your flight’s allowance, as classes can have subtle differentiations, and carry-on allowance may vary by aircraft and route.

  • How does KAYAK find such low prices on flights from Boston to Trinidad and Tobago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Trinidad and Tobago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Trinidad and Tobago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Trinidad and Tobago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Trinidad and Tobago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Boston to Trinidad and Tobago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Trinidad and Tobago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Boston to Trinidad and Tobago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Trinidad and Tobago

  • Travelers who plan to visit the south Caribbean twin island nation of Trinidad and Tobago can find plenty of flights with competitive rates when they depart from Boston Logan International Airport (BOS). Boston Logan International Airport offers service to destinations worldwide and is a Cape Air and Delta hub. This airport is also an operating base for JetBlue.
  • Trinidad, the largest of the two islands, offers sports, festivals, nightlife, museums, and an urban Caribbean feel in its modern capital, Port-of-Spain. Piarco International Airport (POS) serves Trinidad, and passengers can find flights on American Airlines, JetBlue, United Airlines, Air Canada, Caribbean Airlines, and British Airways. Flights between Boston and Trinidad will have at least one layover.
  • Tobago is known for ecotourism, and the smaller islands have a rainforest that has been protected since 1776. Tobago is served by ANR Robinson International Airport (TAB), and Air Canada and Caribbean Airlines offer service between Boston and Tobago. Flights between Boston and Tobago typically have 2 stops.
  • Many travelers enjoy taking advantage of airport lounges before departing on a long flight. Boston Logan International Airport offers several airline lounges, including American Airlines Admirals Club, United Club, and Delta Sky Club.
  • Travelers who want the quickest flight times should plan to fly to Piarco International Airport in Trinidad, which offers the shortest flight durations from Boston. Flights from Boston to Piarco International Airport average around 9-11 hours, while accessing Tobago directly takes about 19 hours.

Reviews of the top 5 airlines serving from Boston to Trinidad and Tobago

 
Need help choosing which airline to fly with from Boston to Trinidad and Tobago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Copa AirlinesOverall score based on 1577 reviews
6.8Entertainment
7.8Boarding
6.8Food
7.4Comfort
8.1Crew
Airline reviews

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

2.0 MediocreFiruz, Apr 2026
MEX - PTY
Read more Copa Airlines reviews

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Boarding was confusing from staff telling going to preboard and than to group 1 Airplane was not cooling at the beginning

Flight got delayed; had to go through security three times.

Copa staff at PTY and one particular crew member were unhelpful & rude.

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Some of the Air hostesses are not that friendly. Need improvement

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Purchased through 3rd party vendor which made everything difficult. Unable to check in online. Unable to get flight updates easily, tsa precheck information didn’t carry through, longer time to check in in person. Entertainment looked good but had to purchase conventional headphones to view.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

Not having an assigned seat until boarding and then having to check my bag.

Flight emergency landed in Chicago due to “Odor” in back of plane . Had to buy ANOTHER TICKET to get to Boston cash out of my own pocket . Then they would notchange my return flight time without a 400. Charge!!!! Insulting.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Flight was as expected. But it was delayed an hour. Also, my luggage got damaged. So that sucked especially since the damage made navigating the airport difficult. Walking to get ground transportation is sooo far away now and my checked bag was difficult to carry.

we were an hour delayed after boarding and given no reason. Headsets cost money. Also there were openrows with no one setting in them but we were told we were not allowed to swtich.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

shittiest airline in the hemisphere. To improve - start thinking you're flying people, not cattle

Easy boarding, inflight refreshments came on time and comfortable seat

It was good that our flight left early. It was a nice smooth flight and landing.

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

Flight home was delayed multiple times, did not get home until 2am

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

My original flight was cancelled and then rebooked four hours later on a recovery flight, but I was checked in as stanby and had no seats so as a family of four we were concerned about not being seated altogether. Our flight then got delayed by another 1.5 hours and when seats were assigned at the gate, three of the four of us were together and we could get my wife closer, they offered no assistance.

I bought a ticket from Kayak. When I got to the airport, the was no ticket. I had to pay 5X to get to my destination. No response received from Kayak. I will NEVER use them again.

Everything you need to know for your flight from Boston to Trinidad and Tobago

Information on your arrival and departure airports