$243 Find Cheap Flights from Port of Spain to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Port of Spain to Massachusetts departing on 6/22. 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

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 in flight searches from Port of Spain to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Massachusetts, as well as popular online travel agencies
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Best Massachusetts Flight Deals from Port of Spain

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston2 stops$447
Boston
Boston2 stops$447

Cheap Flights from Port of Spain to Massachusetts

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Port of Spain to Massachusetts 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 Port of Spain to Massachusetts

Fri, Jul 11 - Sun, Jul 13
Air Canada Logo
2:20 am - 9:56 pmPOS-BOS
19h 36m2 stops
Air Canada Logo
12:15 pm - 1:20 amBOS-POS
13h 05m1 stop
$447Air Canada
Find Deal
Sun, Aug 3 - Sat, Sep 13
Air Canada Logo
2:20 am - 9:55 amPOS-BOS
31h 35m1 stop
Air Canada Logo
6:55 pm - 1:25 amBOS-POS
30h 30m1 stop
$449Air Canada
Find Deal
Tue, Aug 26 - Tue, Sep 9
United Airlines Logo
12:30 am - 12:36 pmPOS-BOS
12h 06m1 stop
United Airlines Logo
7:30 am - 11:23 pmBOS-POS
15h 53m1 stop
$556United Airlines
Find Deal
Wed, Jul 9 - Mon, Jul 14
United Airlines Logo
12:30 am - 11:44 pmPOS-BOS
23h 14m1 stop
United Airlines Logo
8:20 pm - 11:23 pmBOS-POS
27h 03m2 stops
$557United Airlines
Find Deal
Thu, Aug 28 - Tue, Sep 9
JetBlue Logo
7:29 pm - 7:44 amPOS-BOS
12h 15m1 stop
JetBlue Logo
5:15 am - 2:34 pmBOS-POS
9h 19m1 stop
$564JetBlue
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Wed, Aug 27 - Tue, Sep 9
American Airlines Logo
3:35 pm - 12:48 amPOS-BOS
9h 13m1 stop
American Airlines Logo
5:47 am - 2:16 pmBOS-POS
8h 29m1 stop
$574American Airlines
Find Deal
Thu, Aug 28 - Wed, Sep 10
American Airlines Logo
7:00 am - 4:17 pmPOS-BOS
9h 17m1 stop
American Airlines Logo
7:25 pm - 2:16 pmBOS-POS
18h 51m2 stops
$578American Airlines
Find Deal
Thu, Jul 3 - Sun, Jul 13
JetBlue Logo
8:50 am - 12:27 amPOS-BOS
15h 37m1 stop
JetBlue Logo
7:10 am - 6:04 pmBOS-POS
10h 54m1 stop
$595JetBlue
Find Deal
Thu, Aug 28 - Wed, Sep 10
Copa Airlines Logo
3:48 am - 10:31 pmPOS-BOS
18h 43m1 stop
Copa Airlines Logo
8:41 am - 1:48 amBOS-POS
17h 07m1 stop
$739Copa Airlines
Find Deal
Thu, Aug 28 - Wed, Sep 10
Copa Airlines Logo
3:48 am - 10:31 pmPOS-BOS
18h 43m1 stop
Copa Airlines Logo
8:41 am - 1:48 amBOS-POS
17h 07m1 stop
$740Copa Airlines
Find Deal
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KAYAK's insights & trends for Port of Spain to Massachusetts flights

Get data-powered insights and trends into flights from Port of Spain 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 Port of Spain to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Port of Spain 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 Port of Spain 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.

What’s the cheapest day of the week to fly from Port of Spain to Massachusetts?

The average price of all round-trip flights from Port of Spain to Massachusetts clicked on KAYAK for each day over the last 12 months.

When flying from Port of Spain to Massachusetts, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to Port of Spain, you’ll find the best rates on Wednesdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Port of Spain to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Port of Spain 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 Port of Spain 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 seasonJuly
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 16% increase in price.
Flight from Port of Spain to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Port of Spain 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 Port of Spain to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Port of Spain to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Port of Spain 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 Port of Spain 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 Port of Spain 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 Port of Spain 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 Port of Spain 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 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 Port of Spain to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Port of Spain to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. 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 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.
7.5
Copa AirlinesOverall score based on 1451 reviews
6.8Food
7.4Comfort
6.8Entertainment
7.8Boarding
8.1Crew
Airline reviews

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.

2.0 MediocrePaul, Jun 2025PTY - MIA
Read more Copa Airlines reviews

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.

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

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....

My flight delayed and i misss the connection they send me to orlando no to tampa i have to pay a uber to my house

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.

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 🙃

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

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

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 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Airbus plane, nice and polite staff, entertainment even as it was a short flight.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

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.

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

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.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

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 .

I had a nice flight with free wifi. So I was able to message family members and stream music during my flight, which made the trip go by fast. I also enjoyed flying on there Airbus A220. The plane looked very new and it also got up to speed fast down the runway and didn't need much runway to get airborne.

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