$214 Find Cheap Flights from the Cayman Islands to Massachusetts - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from the Cayman Islands to Massachusetts departing on 12/12. 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, 0 bags

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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Booking Insights

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 5 days.

The cheapest ticket to Massachusetts from the Cayman Islands found in the last 5 days was to Boston, at $367 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 5 days was $367.

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 February, when tickets cost $158 (return) on average. On the other hand, the most expensive months are October and July, when the average cost of round-trip tickets is $259 and $258 respectively.

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

The average price for all round-trip flights from the Cayman Islands 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 in the afternoon, when round-trip flights cost $305 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 $1,732.

Good to know

Low seasonNovember
Cheapest flight$214
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly and prices are also 37% 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 $327. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $327 on average.

Reviews of the 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.
7.1
American AirlinesOverall score based on 11715 reviews
6.4Food
7.9Crew
6.8Entertainment
7.2Comfort
7.5Boarding
Airline reviews

Flight cancelled. Twice. And no communication. No gate agent. Went past boarding time and had to go and see email from AA. Airport communication was bad

2.0 MediocreAnonymous, Jun 2026
DFW - PSP
Read more American Airlines reviews

Flight cancelled. Twice. And no communication. No gate agent. Went past boarding time and had to go and see email from AA. Airport communication was bad

I love the e fact that the staff communicated swiftly when my flight was delayed and gate number changed

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

Delayed and horrible communication and sat on flight for an hour before taking off

I was a Wheelchair Assist’ passenger on a London Heathrow to PHL flight yesterday. The process of getting me and my carry-on bag from the ticket counter to the gate was not good at all. It was the worst in my 5 years of experience using this service offered by American. The Philadelphia ‘Wheelchair Assist’ service was, and always has been Excellent! Not so at Heathrow. I was handed off to three different wheelchair drivers; had to sit in a very dingy holding area for 30 minutes while waiting for our gate change announcement; got crammed into a overloaded service vehicle to take me from the holding area to the gate ; was dumped at the end of the line of already-boarding passengers with my heavy carryon and no one helped me up the ramp way at the gate to board the plane. Overall it was a miserable experience!

Flight was delayed three times and we had an international connecting flight which we would’ve missed but AA manage to find us a flight that allowed us to catch and we made our international flight. However, due to the flight change, I’m in Amman, Jordan missing all 4 bags. It’s been a nightmare. Been waiting since June 17 and today is June 20th. Still without luggage. Customer service wait times are two hours and I get disconnected while waiting. I’ll update when/if my luggage arrives. Every day is costing money in a hotel in Amman. I can’t continue my trip to Palestine until the luggage arrives. Then, I will be updating my review.

They did not offer coffee on a 7am flight…awful!!

Plane temperature was so hot that everyone on the plane was sweating. Departure gates changed 3 times in the hour before the flight. Internet service was so poor in the terminal that updates weren't always being received.

We had a mechanical delay which made us 90 minutes late (9:30 PM) then land and put into the penalty box because a plane was in our gate? What the hell! We should get priority.Damn American.

Check in for 5am flight at RDU was hampered by American check in counters being seriously understaffed , was told even supervisor called out. Took so long in line for special services check in that we missed our 5am departure even after arriving at 3:30am. Had to be rescheduled to later flight from Charlotte to St Thomas.

For whatever reason, I could not check in online. Kept getting the "It's not you it's us" message. Even when we tried the kiosk at the airport - same results. The check-in person had a very difficult time getting our boarding passes together despite the fact that we could show confirmation on the jetblue website. After a very long time we finally got boarding passes. The only other issue is, my vegetarian meal featured chicken.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

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.