$400 Find Cheap Flights from the Cayman Islands 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 flight to Massachusetts?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest ticket to Massachusetts from the Cayman Islands found in the last 72 hours was to Boston, at $1,402 round-trip. The most popular route is George Town (GCM) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $1,402.

What is the cheapest month to fly from the Cayman Islands to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from the Cayman Islands 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 the Cayman Islands to Massachusetts is November, when tickets cost $273 (return) on average. On the other hand, the most expensive months are May and June, when the average cost of round-trip tickets is $577 and $567 respectively.

Which is the cheapest airport to fly into in Massachusetts?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $382.


Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$400
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from George Town to Boston

FAQs for booking flights from the Cayman Islands to Massachusetts

  • How does KAYAK find such low prices on flights from the Cayman Islands 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 the Cayman Islands to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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 Saturday where round-trip tickets can be as cheap as $330. On the other hand, the most expensive day to fly is Monday, where round-trip prices are $453 on average.

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

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $330 on average. Morning departures are around 100% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $353.

Top airlines flying from the Cayman Islands 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 the Cayman Islands 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 the Cayman Islands 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.
7.3
JetBlueOverall score based on 2922 reviews
6.7Food
8.0Crew
7.3Entertainment
7.5Boarding
7.6Comfort
Airline reviews

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.

6.0 GoodKristina, Jun 2025SMF - BOS
Read more JetBlue reviews

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.

Book cheap flights from the Cayman Islands to Massachusetts

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Massachusetts found on KAYAK in the last 72 hours.
7/14Mon
1 stopUnited Airlines
9h 09mGCM-BOS
7/18Fri
1 stopUnited Airlines
8h 05mBOS-GCM
$400
7/14Mon
2 stopsUnited Airlines
20h 22mGCM-BOS
7/18Fri
2 stopsUnited Airlines
19h 26mBOS-GCM
$404
7/4Fri
2 stopsUnited Airlines
33h 24mGCM-BOS
7/10Thu
1 stopUnited Airlines
19h 59mBOS-GCM
$411
7/2Wed
2 stopsUnited Airlines
28h 43mGCM-BOS
7/9Wed
1 stopUnited Airlines
8h 05mBOS-GCM
$421
8/7Thu
2 stopsAmerican Airlines
16h 25mGCM-BOS
8/10Sun
1 stopAmerican Airlines
6h 31mBOS-GCM
$449
7/3Thu
1 stop
10h 08mGCM-BOS
7/10Thu
1 stop
6h 55mBOS-GCM
$489
8/7Thu
1 stopAmerican Airlines
8h 04mGCM-BOS
8/10Sun
1 stopAmerican Airlines
6h 31mBOS-GCM
$490
7/3Thu
2 stopsUnited Airlines
43h 21mGCM-BOS
7/9Wed
1 stopUnited Airlines
8h 05mBOS-GCM
$501
7/3Thu
1 stop
10h 08mGCM-BOS
7/10Thu
2 stops
10h 09mBOS-GCM
$508
7/3Thu
2 stopsSouthwest
10h 00mGCM-BOS
7/9Wed
2 stopsSouthwest
16h 00mBOS-GCM
$514

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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.
6/19Thu
multi-stopUnited Airlines
9h 09mGCM-BOS
6/24Tue
multi-stopUnited Airlines
8h 05mBOS-GCM
$485
6/19Thu
multi-stopUnited Airlines
24h 48mGCM-BOS
6/24Tue
multi-stopUnited Airlines
20h 55mBOS-GCM
$489
6/19Thu
multi-stopUnited Airlines
19h 46mGCM-BOS
6/23Mon
multi-stopUnited Airlines
29h 45mBOS-GCM
$503
6/19Thu
multi-stopAmerican Airlines
9h 00mGCM-BOS
6/23Mon
multi-stopAmerican Airlines
16h 45mBOS-GCM
$519
6/19Thu
multi-stopUnited Airlines
20h 41mGCM-BOS
6/23Mon
multi-stopUnited Airlines
27h 55mBOS-GCM
$559

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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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