$243 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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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 $769 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.


Good to know

Low seasonMarch
High seasonAugust
Cheapest flight$243
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly with an average 11% increase in price.
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.

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.
7.5
Copa AirlinesOverall score based on 1452 reviews
8.1Crew
6.8Food
7.8Boarding
7.4Comfort
6.8Entertainment
Airline reviews

It was ok. However, the food was quite poor since I don't eat pasta.

6.0 GoodFernando, Jun 2025PTY - MVD
Read more Copa Airlines reviews

It was ok. However, the food was quite poor since I don't eat pasta.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

I upgraded myself to Business Class at the last minute so I had a DREAMS window seat. Seeing as I've never flown Business before everything was novel and fun for me and it made the 7 hour flight much more enjoyable for sure.

No headphones given for inflight entertainment. I missed my flight from the previous day and the customer service agent tried to extort an additional $100.00 US from me for missing my flight. Really?!

It was reasonably comfortable trip considering its duration (7 hours). Crew was very good and friendly, seats very more comfortable than other planes. Only negative comment would be that the bathroom light did not get its full brightness 🙃

It was good, plane is a bit older so seats are somewhat flat

Great from check in all the way to the end. Very happy with Copa

Copa stranded us ans then tried to charge us thousands to leave Panama.

Gate agent did not hold flight for connection, provided no assistance to get new flight

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

United airlines, mediocre at best. No issues , nothing great . Worked for me

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

The gate and ground staff were excellent, friendly, went out of their way to acknowledge my Mosaic status. The plane was an older Airbus, so the seats were a little worn. The in flight attendant was not very nice, and seemed to be annoyed to be at work or be on this flight. Flight was fast and we landed early and pilots kept us informed.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

The inflight system with their wifi is a hot mess and doesn't work. Separately they do, but when you try to do theoretically simple things like pair a device for control it all falls apart

It was too hot in the cabin. The AC did not help.

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

No space in overhead bin, one cookie, 2 oz of juice - is not customer service.

Good flight, friendly crew and overall - good service on United Airlines.

Received email saying that there won’t be a seat back entertainment screen and inflight WiFi would be available. But no WiFi both ways. Say it in the email.

Somebody either kayak or Air Canada booked my flight under my preferred name Betty instead of my legal name and I almost was denied boarding my flight

flight landed late almost 1.00hr and we 4 passengers missed our connected flight to indianapolis, we need to get the hotel and taxi for the next day flight to home in indianapolis, cost us $ 300 more

Or the greatest and it ended up picking us up from Chicago to Toronto not sure who was tesponsible for the 4 hr delay. United should have been properly prepared for a scheduled flight from Austin to Chicago and they were not.

Good, only discomfort was consistent turbulence through the 3 hour flight. Not sure if in companies control though.

From the kind young lady (w/Vancouver air security) who expedited our check-in to U.S. Customs to the Air Canada gate crew who gave us pre-boarding, the flight attendants who actually offered a strong hand to help me board once I had surrendered my rolling walker at the door, they are all reflections of the thoughtful, genuinely helpful Canadians we have grown to appreciate. Water and other beverages were offered throughout the flight to make sure we weren't dehydrated and the cookie was great. (Husband bought the fruit & crackers snack,) I was delighted to see three movies that I would not have otherwise seen and appreciate that AC left the last film viewable until its conclusion although the flight had actually landed. Last, mahalo to the kind strong gentleman who not offered his hand to help me debark the plane, but gave me an AC pin that I'll truly treasure.

The ground staff was so rude in Toronto airport ...very rude and did not answer simple questions, and made me look like a fool. Very rude ground staff.

My flight got delayed 5 times and then got cancelled eventually, I had to get a hotel and uber and pay for food for an extra night without any plans. It was a horrible experience, instead of Air Canada, I was flying with United .

Book cheap flights from Trinidad and Tobago to Massachusetts

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Massachusetts found on KAYAK in the last 72 hours.
7/11Fri
1 stopAir Canada
15h 48mPOS-BOS
8/23Sat
2 stopsAir Canada
30h 40mBOS-POS
$449
7/11Fri
2 stopsAir Canada
31h 15mPOS-BOS
8/23Sat
2 stopsAir Canada
30h 40mBOS-POS
$460
8/27Wed
1 stopCopa Airlines
31h 53mPOS-BOS
9/9Tue
1 stopCopa Airlines
9h 59mBOS-POS
$522
7/7Mon
2 stopsUnited Airlines
18h 48mPOS-BOS
7/22Tue
2 stopsUnited Airlines
17h 53mBOS-POS
$555
8/26Tue
1 stopUnited Airlines
14h 12mPOS-BOS
9/9Tue
1 stopUnited Airlines
15h 53mBOS-POS
$556
8/27Wed
1 stopCopa Airlines
18h 42mPOS-BOS
9/10Wed
1 stopCopa Airlines
17h 07mBOS-POS
$559
7/8Tue
1 stopJetBlue
14h 22mPOS-BOS
7/16Wed
1 stopJetBlue
12h 49mBOS-POS
$573
8/28Thu
1 stopAmerican Airlines
16h 45mPOS-BOS
9/9Tue
1 stopAmerican Airlines
8h 29mBOS-POS
$574
8/28Thu
1 stopAmerican Airlines
17h 48mPOS-BOS
9/10Wed
2 stopsAmerican Airlines
20h 58mBOS-POS
$578
7/2Wed
1 stopJetBlue
13h 25mPOS-BOS
7/9Wed
1 stopJetBlue
10h 54mBOS-POS
$629

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Massachusetts found on KAYAK in the last 72 hours.
6/22Sun
1 stopAir Canada
20h 11mPOS-BOS
$243
7/8Tue
1 stopCopa Airlines
18h 39mPOS-BOS
$291
7/7Mon
2 stopsUnited Airlines
22h 40mPOS-BOS
$305
8/21Thu
3 stopsUnited Airlines
44h 55mPOS-BOS
$310
7/6Sun
2 stopsUnited Airlines
34h 27mPOS-BOS
$311
7/10Thu
1 stopJetBlue
12h 09mPOS-BOS
$314
8/22Fri
1 stop
28h 31mPOS-BOS
$336
7/20Sun
3 stops
30h 43mPOS-BOS
$351
7/10Thu
2 stopsAmerican Airlines
29h 48mPOS-BOS
$365
7/12Sat
2 stopsAmerican Airlines
28h 20mPOS-BOS
$457

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Last minute flights to Massachusetts

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Massachusetts that are departing in the next 10 days.
6/18Wed
multi-stopUnited Airlines
14h 11mPOS-BOS
6/25Wed
multi-stopUnited Airlines
17h 18mBOS-POS
$846
6/19Thu
multi-stopJetBlue
13h 14mPOS-BOS
6/25Wed
multi-stopJetBlue
12h 54mBOS-POS
$994
6/19Thu
multi-stopAmerican Airlines
17h 09mPOS-BOS
6/25Wed
multi-stopAmerican Airlines
11h 45mBOS-POS
$1,008
6/19Thu
multi-stop
24h 26mPOS-BOS
6/25Wed
multi-stop
26h 24mBOS-POS
$1,323
6/19Thu
multi-stop
26h 08mPOS-BOS
6/25Wed
multi-stop
26h 24mBOS-POS
$1,369

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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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