$243 Find Cheap Flights from Trinidad and Tobago to Massachusetts

1 adult

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

Save 22% 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.

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 day to fly to Massachusetts?

The average price of all flights from Trinidad and Tobago to Massachusetts clicked on KAYAK for each day over the last 12 months.
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 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 October, when tickets cost $424 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $771 and $697 respectively.

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

The average price for all round-trip flights from Trinidad and Tobago to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
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.

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. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

March

High season

July

Cheapest flight

$243
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 12% 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.

See more FAQs

Top 4 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 1409 reviews
6.8Entertainment
8.1Crew
7.8Boarding
6.8Food
7.4Comfort
Airline reviews

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.

10.0 ExcellentLisa, Mar 2025PTY - LAX
Read more Copa Airlines reviews

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 🙃

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

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.

I loved my experience. Very safe, Very informative and very friendly.

Flight attendant -José? - was over the top friendly and professional. Beautiful new plane with lie flat seats in Business (worth it!)

Horrible food. No wine or any other alcohol is served on the flight. Water is not served often and they refused when I asked for water in two cups. On the other hand, both going and coming back flights were on time.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

leg space better than expected. two washrooms for one plane isn't enough.

My suitcase was destroyed. The top part where the handle is is completed broken. And unusable now.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

I love United was disappointed we had a two hour delay, however the Pilot did say safety first.

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

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.

The regular feedback of any changes to our flights. The Jetblue staff were very helpful. Our flights were great. Lots of leg room!

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

There were five broken seats on the plane. The crew was very rude in telling people they had to get off the plane and get a flight the next day. No call for volunteers, but telling people they had to get off. One woman was flying with her elderly mother and daughter and was told she had to leave or all three had to leave. Fortunately, a volunteer offered to stay. The situation was handled poorly.

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Any sort of gluten free snack option would be nice

They lost my luggage and it didn’t get delivered until the next day.

Would have thought that they would gas up plane before everyone got on board

3 hours late. Not even water offered on a 2.25 hour flight.

I had a carry on and a personal bag. I put my personal item under my seat and on way to the seat I put my bag up. I usually close my eyes and rest as I was on call for last 36 hours. I heard very loud announcements that someone needs to identify their bag. Pretty sure it was not mine until the hostess pointed out my jacket details attached to the bag. I asked why she got my bag out. I got berated and did not want to create a scene. But this person needs to be talked to.

Terrible. The flight was delayed two hours due to weather. Then when we got on the plane, the first pilot ended up timing out and we had to wait for a second pilot. Second pile came on board and we tax it out. Had to return back to the gate because of an unruly passenger. Then the copilot timed out. Had to wait for new copilot. Also had to wait for maintenance to check for fuel. Then found out the second pilot timed out and we had to wait for a third pilot. Was ready to go and then needed maintenance again for another issue. In the end, it was 2 o’clock in the morning when they announced that the flight couldn’t go because the third pilot and the second copilot had timed out.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

American Airlines initially postponed the flight. Then they cancelled it an rescheduled us on a flight that would take over 24 hours with multiple stops. They then changed this flight to a reasonable alternative the next day which they later cancelled and replaced with a flight that would take off with an additional 16 hour delay. They blamed weather but I noticed (at 4am) that Delta had direct flights from Charlotte to Detroit. I went on line. Booked it and was in Detroit buy 9am. The interesting thing is they did a similar thing to a family member just 2 days earlier. I don't think I will fly American unless I have to.

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.
7/10Thu
1 stop
14h 29mPOS-BOS
7/17Thu
1 stop
12h 00mBOS-POS
$530
7/13Sun
1 stop
16h 05mPOS-BOS
7/20Sun
1 stop
12h 00mBOS-POS
$547
7/9Wed
2 stopsUnited Airlines
17h 36mPOS-BOS
7/17Thu
1 stopUnited Airlines
18h 08mBOS-POS
$552
7/12Sat
2 stopsUnited Airlines
34h 29mPOS-BOS
7/20Sun
2 stopsUnited Airlines
41h 13mBOS-POS
$561
8/4Mon
1 stopAmerican Airlines
9h 40mPOS-BOS
8/27Wed
1 stopAmerican Airlines
8h 30mBOS-POS
$574
7/10Thu
2 stopsAmerican Airlines
16h 45mPOS-BOS
7/17Thu
2 stopsAmerican Airlines
13h 19mBOS-POS
$579
6/13Fri
1 stopJetBlue
8h 06mPOS-BOS
6/21Sat
1 stopJetBlue
10h 49mBOS-POS
$617
7/10Thu
1 stopCopa Airlines
18h 39mPOS-BOS
7/21Mon
1 stopCopa Airlines
9h 42mBOS-POS
$761
4/29Tue
1 stopJetBlue
13h 41mPOS-BOS
5/3Sat
1 stopJetBlue
8h 11mBOS-POS
$766
7/12Sat
1 stopCopa Airlines
18h 39mPOS-BOS
7/20Sun
1 stopCopa Airlines
9h 42mBOS-POS
$968

Search by stops

Search by airline

Search by price

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.
5/30Fri
1 stopAir Canada
13h 23mPOS-BOS
$243
5/16Fri
1 stopAir Canada
31h 30mPOS-BOS
$248
6/30Mon
2 stopsUnited Airlines
23h 29mPOS-BOS
$303
6/30Mon
1 stopUnited Airlines
21h 30mPOS-BOS
$305
6/30Mon
3 stopsUnited Airlines
33h 19mPOS-BOS
$309
5/8Thu
1 stopJetBlue
11h 33mPOS-BOS
$312
5/17Sat
1 stopAmerican Airlines
18h 50mPOS-BOS
$314
7/1Tue
2 stopsAmerican Airlines
14h 40mPOS-BOS
$318
5/7Wed
3 stops
39h 14mPOS-BOS
$319
5/7Wed
1 stopCopa Airlines
15h 42mPOS-BOS
$482

Search by stops

Search by airline

Search by price

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.
4/19Sat
multi-stopJetBlue
8h 51mPOS-BOS
4/21Mon
multi-stopJetBlue
10h 48mBOS-POS
$1,136
4/19Sat
multi-stop
15h 35mPOS-BOS
4/21Mon
multi-stop
48h 05mBOS-POS
$1,238
4/18Fri
multi-stop
17h 24mPOS-BOS
4/21Mon
multi-stop
22h 18mBOS-POS
$1,251
4/18Fri
multi-stop
17h 24mPOS-BOS
4/21Mon
multi-stop
47h 35mBOS-POS
$1,382
4/19Sat
multi-stop
24h 11mPOS-BOS
4/21Mon
multi-stop
47h 35mBOS-POS
$1,389
4/18Fri
multi-stopUnited Airlines
11h 57mPOS-BOS
4/21Mon
multi-stopUnited Airlines
16h 03mBOS-POS
$2,034

Search by stops

Search by airline

Search by price

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.