$249 Find Cheap Flights from Trinidad and Tobago to Massachusetts

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Massachusetts, as well as popular online travel agencies
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Booking Insights

KAYAK's insights & trends for flights to Massachusetts

Get data-powered insights and trends for flights to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Trinidad and Tobago to Massachusetts, 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 Trinidad and Tobago to Massachusetts is May, when tickets cost $414 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $771 and $753 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Massachusetts, 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 Trinidad and Tobago to Massachusetts, you should book around 3 weeks before departure, which saves you about 20% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonApril
Cheapest flight$249
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Port of Spain to Boston

FAQs for booking flights from Trinidad and Tobago to Massachusetts

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

    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 Trinidad and Tobago to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Trinidad and Tobago to Massachusetts 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 Trinidad and Tobago to Massachusetts?

    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 Trinidad and Tobago to Massachusetts 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 Trinidad and Tobago to Massachusetts?

    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 Trinidad and Tobago to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Thursday where round-trip tickets can be as cheap as $531. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $657 on average.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $580 on average. Morning departures are around 12% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $680.

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

 
See real verified KAYAK customer reviews for airlines flying to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Trinidad and Tobago to Massachusetts. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Trinidad and Tobago to Massachusetts? 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.
7.6
Copa AirlinesOverall score based on 1531 reviews
7.8Boarding
8.1Crew
6.8Entertainment
6.8Food
7.4Comfort
Airline reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

10.0 ExcellentNeil, Aug 2025PTY - BGI
Read more Copa Airlines reviews

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

Cops Airlines is fantastic! The level of care and professionalism provided by the entire crew was top rate.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Great experience with a crew always thinking in the passenger

I selected first class expecting excetional service. It was mediocre at best. The food service was cold, meal choices was poor and on one leg they did provide dessert. I did enjoy the lay day seat but the movies were old and nothing current. Boarding the plane is always hot. So boarding is quite warm until your in the air. I took a small personal air fan. Update the meals and movies.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

The newer screen was super cool and had the option to watch many different shows or movies. Crew was polite and helpful. However again, many children screaming bloody murder and kicking my seat, and parents doing nothing about it as usual.

Flight was good and crew was super polite. However, there were around 5 kids screaming the WHOLE 2 hours. I understand kids have to come but parents need to do something to control their children. They make the experience terrible, especially after finishing 16 hour shifts at the hospital I needed some sleep, which I did not get.

IAD with the archaic people movers is just a place to be avoided.

Overall, it was good. I was seating next to a wonderful lady and did not notice how time flew. Thanks

All of the United employees I interacted with were professional and courteous. The aircraft was clean, the food on the flight was good. No complaints here.

Armrest controller on my seat 35D and nextbooennseat 35E did not work right. Hard to press buttons to recognize and 35D had constantnpressure either upmost down somit was nearly impossible to make selections. .

I flew with my dog and had already purchased my dog’s ticket. Even that morning I had called costumer service to insure that my husband and I had seats together since the website was giving me an error when choosing our seats and the representative mentioned our dog. I showed up early to the airport and when I got to the gate and we started boarding I was help back and told that I was supposed to have a yellow tag and that I should have checked in at the counter for them to give me that tag. I was not aware of this, the representative on the phone did not say anything. Nor did I see it anywhere in the checking process online, so if you travel with a pet and are not checking in luggage, just know that you still have to go to the check in counter when arriving at the airport unless you want to be the last one to board and not have room for your carry on in the overhead bins. Other than that, I had a great experience.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

This is the best united airlines flight that I took. The crew was very friendly and the food was tasty!

Given it’s a red-eye into Charolotte, we didn’t get any food. The survey does not include “N/A” so the rating will be skewed.

The delayed flight was awful and moving the departure gate twice was annoying

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

The flight was on time and crew were nice, seats were tight and there was entertainment available

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

There's nothing I liked about it. For first off I scheduled this trip two weeks in advance then they delayed my flight which messed up my whole trip. So I scheduled it for the following weekend thinking there won't be a delay and guess what as soon as I got to the airport we said in the airplane on the tarmac for an hour and a half. Not only was it delayed I missed my connecting flight meaning I had to stay the night at Dallas-Fort Worth airport sleeping on the floor. I will tell you this I will never fly American airlines ever again I have had nothing but horrible experience with them and I just throw money at them

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Having to reschedule flights a day later, they loaded by luggage on the wrong plane from Little rock now I have to HOPE they deliver it to where im staying like they said would. International flight crew was very disgruntled and not very friendly.

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

It took way too long to diagnose and solve the problem of a broken crew member cabin seat. Though compensation for the volunteer who left the flight was very kind.

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

flight cancelled after 2 delays. left us sitting in JFK at 1am. no customer service to assist rebooking.

I liked the behaviour of the crew members.The flight was good.

1 hour late No hot drinks No restroom in the back of the plane

I swear airplane seats keep getting smaller and smaller but everything else was great. Smooth sailing and we got in early.

No food to provide, they forgot that, in some cases, people stay at the airport for hours without food. Now, to provide them with food, they have to ask them to pay, because some don't have money. That way, they can't eat.

After a long flight from Tokyo, our connecting flight home was canceled due to “maintenance” while we were on our layover in Toronto. Very frustrating to close out our honeymoon, although I’m sure others had it even worse during last week’s strike. Air Canada staff at Pearson Airport are the one thing that kept me remotely at peace during this — they were very helpful and deserve a lot of props. But I would not fly Air Canada again.

I had wonderful wheelchair assistance through the Montreal airport onto the flight. Air Canada was excellent in this both at the Fredericton airport and the Montreal one where an attendant helped us through customs as well as transport and baggage security.

Horrible flight cancelled had to buy another very expensive ticket

Flight was cancelled last minute due to Air Canada strike leaving us stranded and having to stressfully find a way home that cost hundreds of dollars in excess cost added to the trip. Having just experienced our mother's funeral service, this was not a good way to end our trip.

Air Canada marooned me in Canada with no way back home during my summer vacation. I had to buy a last minute flight ticket for over $500 to make it back home. I have their credit card and have flown them for years. Never again.

Flight was cancelled last minute. Had to scramble and purchase a $2000 flight through a separate airlines. Stuck in Toronto two extra days. Missed my first two days on a new job. Had to rent a car for an additional two days. Scrambled to fins a place to live those extra two days. Spent a ton of extra money and lost a lot of money, as well as made a poor impression at work. Difficult difficult difficult

Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Massachusetts

Cabin classes available on flights to Massachusetts. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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