$302 Find Cheap Flights from Port of Spain to Massachusetts - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Port of Spain to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Boston
9h 02m2 stops
from $519per person
Booking Insights

Price, demand and travel trends for Port of Spain to Massachusetts flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Port of Spain to Massachusetts recently?

The cheapest fare from Port of Spain to Massachusetts in the last week was $519 round-trip, to Boston Logan Intl (BOS).

How do fares into airports in Massachusetts compare?

Flights from Port of Spain to Massachusetts arrive at a single airport, Boston Logan Intl (BOS). Round-trip fares average about $505.

What's the cheapest month to fly from Port of Spain to Massachusetts?

February is typically the cheapest month to fly from Port of Spain to Massachusetts, with round-trip fares averaging $268. January and October are usually the most expensive, averaging $813 and $654, respectively.

How do fares from Port of Spain to Massachusetts vary by day of the week?

On average, Saturday is the cheapest day to fly from Port of Spain to Massachusetts and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 74% more expensive to fly on a Sunday compared to Saturday.

What's the best time of day to fly from Port of Spain to Massachusetts?

It's cheapest to fly to Massachusetts in the morning with average prices of $274. The afternoon is the most expensive time to fly, with average prices of $600.

Key details for Port of Spain to Massachusetts flights

Low season

October

Cheapest flight

$302
Beat the crowds with an average 47% drop in travelers.
The most popular month to fly with an average 46% increase in travelers.
One-way flight from Port of Spain to Boston

Your Port of Spain to Massachusetts flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Port of Spain to Massachusetts?

    Fares from Port of Spain to Massachusetts are around their usual level right now. A round-trip under $369 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch fare changes.

  • How much should I budget for a flight from Port of Spain to Massachusetts?

    Over the past 12 months, round-trip fares from Port of Spain to Massachusetts have typically cost between $369 and $642.

  • What are the main airports serving Massachusetts?

    Massachusetts has 12 airports. 100% of KAYAK users choose Boston Logan Intl (BOS) as their arrival airport.

  • Which airlines fly nonstop from Port of Spain to Massachusetts?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Port of Spain to Massachusetts. One-stop options include:

    • American Airlines
    • Caribbean Airlines
    • JetBlue

  • Which destinations in Massachusetts can I fly nonstop from Port of Spain?

    Based on the flight schedule for the next 3 months, there are no nonstop flights from Port of Spain to Massachusetts. The most popular destination you can reach with one stop is Boston.

  • Which cabin classes are available from Port of Spain to Massachusetts?

    On flights from Port of Spain to Massachusetts you can book Economy Class or First Class.

  • What are some popular landmarks around Massachusetts?

    Massachusetts is home to many popular sights. KAYAK travelers' favorites include:

    • TD Garden
    • Fenway Park
    • Boston Common
    • Boston Convention and Exhibition Center

Your guide to booking Port of Spain to Massachusetts flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in February to save some money. It's typically the cheapest month on this route, while flights in January will cost you the most.
  • Fly out on a Saturday to get the cheapest fares. Avoid Sunday flights, which are about 74% more expensive.
  • Start your trip in Boston, the most popular destination in Massachusetts. From there, it's easy to continue on to other popular spots such as Nantucket, Cambridge and Hyannis.

Reviews of the top 4 airlines serving from Port of Spain to Massachusetts

 
Need help choosing which airline to fly with from Port of Spain 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 1555 reviews
7.8Boarding
7.4Comfort
8.1Crew
7.0Food
6.9Entertainment
Airline reviews

We were made to check our carry-on luggage because it did not fit the measurements. That’s what we were told, but I saw plenty of carry-on luggage on the plane that was the same size as ours

4.0 OkayAnonymous, Sep 2026
Read more Copa Airlines reviews

We were made to check our carry-on luggage because it did not fit the measurements. That’s what we were told, but I saw plenty of carry-on luggage on the plane that was the same size as ours

Flight Crew Review The crew was absolutely amazing from start to finish! They were friendly, professional, attentive, and genuinely made the flight feel comfortable and enjoyable. Every interaction was pleasant, and they went above and beyond to make sure passengers were taken care of. You could really tell that they cared about providing great service. I truly appreciate their kindness and professionalism and would be happy to fly with this crew again!

stood in line to check in luggage for nearly an hour. very poor service and not excusable

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

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

Do not book it’s a scam! They stole $1200 from me

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

A lot things happened in this trip.The fly should be less stress.

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

Seemed roomier than most US domestic airlines and they served food.

Check in went smoothly. Flight attendant who was assigned my area barely paid any attention to me! She acted as though she was extremely busy and flustered. Maybe she was new?! I told her to change the language on my screen, she said she’d come back to help me but never did so I was able to solve the problem on my own. She came back and said she’d made adjustments on her end. Highly doubt it because I found the setting to change the language! Also, I noticed everyone was eating before we landed so I pushed my help button and she never came so I got up to find her to ask her if I can have breakfast. She said they are not serving breakfast but I can have a sandwich. Yes, that was her response as I saw everyone eating breakfast!!!

Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.

I missed my flight and had to buy new tickets Rome- Boston

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

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

I like flying first class, and United has a nice one

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

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

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

Entertainment, clean plane and funny pilot over the intercom was excellent… however, gate agent was rude and was probably a Spirit employee before they went bankrupt… there were 3 flight attendants - 2 of them didn’t want to be there the other one was kind and nice… I want you to recognize how you have to compete with Delta or South West airlines or even American Airlines which would choose over you at any given day from here on out. Please treat people respectfully. If you hate working in this industry - go and work somewhere else. The flight was very empty and it shouldn’t be hard to crack a smile once in a while. Very disappointing… I remember flying Jet Blue back in the day from Dulles IAD to LAX and you guys were super cool and fancy and made flying fun again - truly elevated the experience. Don’t become the next most hated airline… you can do better . I want you to succeed…

Free wifi was almost impossible to get, kept dropping the connection

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

The whole experience at the airport in Istanbul should be made known beforehand. Four passport checks and a huge check-in line as I could not check in online made it a very lengthy and frustrating experience. The flights on Turkish Airlines however were just fine.

Late boarding, had to check the bag even though there was space on the flight and I was I row 7

Unacceptable pre-boarding ticket issues. Paid for and reserved Mint seat approximately a month in advance. Checked in to flight in Mint seat 24 hours before flight. Shortly before flight, was bumped out of Mint entirely, even though other Mint seats were still available and for sale. Was told it was "operational", however seats were still available/being sold. Got to gate and they could not explain it, but the gate agent was able to put me back into Mint (however to a different seat). Nothing proactive done by Jetblue, I would have been bumped had I not arrived at gate early enough to have a helpful gate agent rectify. No explanations from Jetblue.

Diana at the gate was unhelpful which was fine, but she was also rude which I did not appreciate at all.

Forced to check bag, even though plenty of space in overhead bins. Did not appreciate having to wait at baggage claim to retrieve suitcase.

To not have food or proper snacks on a 5 hour flight was the worst.

Staff announced flight was delayed. Then after passengers took the extra time to get food etc, announced it was on time. Not enough overhead space for a full flight Seats were super small and crammed. Crew welcomed us aboard to another "on time gate departure” only to sit on the tarmac for two hours. They made 2 announcements as to why that no one could understand. NO ENTERTAINMENT- food was a bag of old pretzrks. After landing, sat on the tarmac for another 20 minutes “looking for a parking spot”. I never fly American due to past poor performance. I had to that day due to departure time. American never fails to disappoint.

The crew was wonderful, the plane was fine. We left the gate on time, but we had to wait 40 minutes on the tarmac because of all the congestion at Boston.

Had to pay for WiFi, delayed start, and sat on the runway forever.

On time departure was much appreciated. However, as a frequent flyer and American Advantage member, I was as disappointed not to get an aisle seat.

Flight was cancelled due to a myriad of operational issues. You guys really suck

boarding sucked they lost my bag never flying Iberia again

Couldn't make the flight because connecting flight was canceled.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Plane features were VERY old and outdated. footrest cushion was completely lose, plane felt dirty and a bit grimy. i was in business class. the lead flight attendant, Mary made a few announcements that didn't seem to put the cabin at ease (it didn't necessarily bother me, but could have bothered others). she said "the seat cushions aren't FDA approved, so you have to put them on after we take flight." everyone had already applied the seat cushions, and saying something isn't approved for flight may cause alarm. she also said at one point over the announcement ... "we can't get up because we are too afraid of the jet stream impacts" -- again, not helpful to those who are nervous fliers.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

More options for your flight from Port of Spain to Massachusetts

Complete your trip to Massachusetts with a hotel stay or car rental