$142 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 5/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Trinidad and Tobago

Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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 Spain2 stops$320
Scarborough
Scarborough2 stops$1,001
Port of Spain
Port of Spain2 stops$320
Scarborough
Scarborough2 stops$1,001

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

Wed, Apr 29 - Tue, May 5
United Airlines Logo
7:15 am - 11:23 pm
BOS
-
POS
16h 08m
2 stops
United Airlines Logo
12:30 am - 12:16 pm
POS
-
BOS
11h 46m
1 stop
$320United Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
6:00 am - 10:59 pm
BOS
-
POS
16h 59m
1 stop
American Airlines Logo
3:12 pm - 12:59 am
POS
-
BOS
9h 47m
1 stop
$323American Airlines
Wed, Apr 29 - Tue, May 5
United Airlines Logo
8:30 am - 11:23 pm
BOS
-
POS
14h 53m
2 stops
United Airlines Logo
12:30 am - 2:26 pm
POS
-
BOS
13h 56m
2 stops
$324United Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
6:00 am - 10:59 pm
BOS
-
POS
16h 59m
1 stop
American Airlines Logo
3:12 pm - 12:59 am
POS
-
BOS
9h 47m
1 stop
$326American Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
11:22 am - 10:59 pm
BOS
-
POS
11h 37m
2 stops
American Airlines Logo
7:00 am - 12:59 am
POS
-
BOS
17h 59m
1 stop
$327American Airlines
Wed, May 27 - Tue, Jun 2
American Airlines Logo
6:00 am - 10:59 pm
BOS
-
POS
16h 59m
1 stop
American Airlines Logo
7:00 am - 10:26 pm
POS
-
BOS
15h 26m
2 stops
$330American Airlines
Sun, May 31 - Thu, Jun 4
American Airlines Logo
6:00 pm - 2:12 pm
BOS
-
POS
20h 12m
1 stop
American Airlines Logo
3:12 pm - 12:59 am
POS
-
BOS
9h 47m
1 stop
$334American Airlines
Sat, May 9 - Fri, May 15
American Airlines Logo
6:22 pm - 2:32 pm
BOS
-
POS
20h 10m
1 stop
American Airlines Logo
3:47 pm - 11:12 am
POS
-
BOS
19h 25m
2 stops
$339American Airlines
Wed, Apr 29 - Mon, May 4
United Airlines Logo
9:41 am - 11:23 pm
BOS
-
POS
13h 42m
1 stop
United Airlines Logo
12:30 am - 5:07 pm
POS
-
BOS
16h 37m
1 stop
$340United Airlines
Sun, May 24 - Sun, May 31
Multiple Airlines Logo
5:45 am - 6:50 am
BOS
-
TAB
25h 05m
2 stops
Multiple Airlines Logo
5:30 pm - 9:49 am
TAB
-
BOS
40h 19m
2 stops
$1,001Multiple 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 May, when tickets cost $425 (return) on average. On the other hand, the most expensive months are February and August, when the average cost of round-trip tickets is $617 and $587 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$142
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 15% 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 1575 reviews
7.4Comfort
8.1Crew
7.7Boarding
6.8Entertainment
6.8Food
Airline reviews

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

10.0 ExcellentK Anson, Apr 2026
POS - PTY
Read more Copa Airlines reviews

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.

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Checking in united could not figure out my star alliance gold. Baggage did not get marked priority and didn't receive boarding passes. When got to SFO lounge personal fixed everything Immediately

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

This was the first flight in the morning. We boarded fine. The cabin door was closed and we were ready to go. We were notified by the Captain that ATC issued and ground stop for 40 minutes. So, without even pushing back from the gate, we were already 40 minutes late. We actually were released to push-back and taxi at 30 minutes. But, some passengers had tight connections and were not going to make their connections. Some passengers asked about the delay and the effect on the connections and were told by the cabin attendant that all flights will be delayed and so they should be OK. However, that was not true. My connecting flight was on time and I arrived at IAH with 21 minutes to make my connection. I did and I'm happy about that, but the flight crew should not have given assurances to the passengers who might have missed their connections.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

All good flight was 35 minutes early when arriving in Edinburgh

Flights were on time actually early service was good and crew cheerful

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Cleared standby and gave up my seat. Terrible policy and boarding experience

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

The WiFi would not connect enough for me to do my actual work. It permaspooled, disconnected, said it was connected, then wouldn't open an email... it was frustrating. I am not a tall person, 5'4" - and I felt cramped with little room to reach into my bag under the seat in front of me. I feel sorry for anyone taller than me having to fly. the one positive thing I will add, is the overhead bins are roomy enough to manage more bags than other carriers.

Air condition was not working for long both after boarding and also after landing ; unbearably hot and suffocating

On time flight, good communication about boarding, lines didn't form unnecessarily for boarding before their group was announced (kept aisles clear), friendly flight attendants and service

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Everything was excellent and I enjoyed myself. Thank for everything

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Boarding was quick and efficient. We arrived at our destination early.

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.

My wallet was stolen while I was sleeping on the plane.

Good boarding but extremely cold temperature in both flights (60 F!).

The whole plane smelled and felt old. The seats were very uncomfortable. Multiple delays. Extra fees.

Very rude gate attendants in San Francisco who didn’t let me bring my little carry on (smaller than usual size) and after boarding I realized that there still were a lot of overhead compartment space (like a full section available in some spots). That made me lose 30 minutes at my destination at 1am and it could have broken something fragile that I had in it

The most uncomfortable flight I’ve ever been on. I’m only 5,4” and barely had enough room to exist, couldn’t even fully relax my shoulders. Not sure why they bother with snacks. Half a coke and a single cookie?? Wow. Purchasable food looked gross too. Remember when airlines used to treat you like a human being?

Departed Palm Springs over an hour late because there’s only one gate, and it has always delayed by the arriving and departing flight to Toronto and the arriving flight from Vancouver.

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

Information on your arrival and departure airports