$90 Find Cheap Flights from Boston to the Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to the Cayman Islands departing on 2/5. 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

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Cheap Flights from Boston to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town2 stops$270
Cayman Brac
Cayman Brac2 stops$1,497
George Town
George Town2 stops$270
Cayman Brac
Cayman Brac2 stops$1,497

Book Cheap Boston to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to the Cayman Islands 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 Boston to the Cayman Islands

sáb., ene. 10 - sáb., ene. 17
United Airlines Logo
7:22 pm - 1:45 pm
BOS
-
GCM
18h 23m2 stops
United Airlines Logo
2:25 pm - 9:57 pm
GCM
-
BOS
7h 32m1 stop
$270United Airlines
dom., ene. 11 - mar., ene. 13
United Airlines Logo
7:07 pm - 1:45 pm
BOS
-
GCM
18h 38m2 stops
United Airlines Logo
2:25 pm - 11:49 pm
GCM
-
BOS
9h 24m2 stops
$275United Airlines
lun., ene. 5 - lun., ene. 12
United Airlines Logo
7:44 pm - 1:15 pm
BOS
-
GCM
17h 31m2 stops
United Airlines Logo
2:50 pm - 10:53 am
GCM
-
BOS
20h 03m1 stop
$277United Airlines
sáb., ene. 3 - sáb., ene. 10
Spirit Airlines Logo
5:45 am - 4:55 pm
BOS
-
GCM
11h 10m1 stop
Spirit Airlines Logo
2:34 pm - 11:57 pm
GCM
-
BOS
9h 23m1 stop
$283Spirit Airlines
sáb., feb. 7 - dom., feb. 8
Spirit Airlines Logo
5:34 am - 1:38 pm
BOS
-
GCM
8h 04m1 stop
Spirit Airlines Logo
2:49 pm - 11:57 pm
GCM
-
BOS
9h 08m1 stop
$284Spirit Airlines
vie., ene. 2 - vie., ene. 9
United Airlines Logo
6:45 am - 1:15 pm
BOS
-
GCM
6h 30m1 stop
United Airlines Logo
2:25 pm - 9:52 pm
GCM
-
BOS
7h 27m1 stop
$285United Airlines
vie., feb. 6 - mar., feb. 10
United Airlines Logo
6:00 am - 1:15 pm
BOS
-
GCM
7h 15m1 stop
United Airlines Logo
2:25 pm - 9:52 pm
GCM
-
BOS
7h 27m1 stop
$288United Airlines
vie., ene. 2 - dom., ene. 11
United Airlines Logo
6:45 am - 1:15 pm
BOS
-
GCM
6h 30m1 stop
United Airlines Logo
2:50 pm - 10:36 am
GCM
-
BOS
19h 46m2 stops
$290United Airlines
mar., dic. 30 - jue., ene. 8
United Airlines Logo
6:45 am - 1:15 pm
BOS
-
GCM
6h 30m1 stop
United Airlines Logo
2:50 pm - 10:52 am
GCM
-
BOS
20h 02m1 stop
$292United Airlines
sáb., abr. 18 - sáb., abr. 25
Multiple Airlines Logo
6:45 pm - 3:25 pm
BOS
-
CYB
21h 40m2 stops
Multiple Airlines Logo
6:20 pm - 10:38 pm
CYB
-
BOS
27h 18m2 stops
$1,497Multiple Airlines
Booking Insights

KAYAK's insights & trends for Boston to the Cayman Islands flights

Get data-powered insights and trends into flights from Boston to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Boston to the Cayman Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Boston found in the last 72 hours was to George Town, at $315 round-trip. The most popular route is from Boston (BOS) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $315.

Can I save money by flying with a layover from Boston to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $499 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to the Cayman Islands, 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 Boston to the Cayman Islands is March, when tickets cost $385 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $644 and $579 respectively.

What’s the cheapest day of the week to fly from Boston to Cayman Islands?

The average price of all round-trip flights from Boston to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cayman Islands on a Wednesday and more expensive on a Saturday. On your return trip to Boston, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

How far in advance should I book a flight from Boston to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to the Cayman Islands, 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 Boston to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$90
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Boston to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Boston to the Cayman Islands?

    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 Boston to the Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to the Cayman Islands 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 Boston to the Cayman Islands?

    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 Boston to the Cayman Islands 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 Boston to the Cayman Islands?

    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 Boston to the Cayman Islands 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 the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the evening, when round-trip flights cost $305 on average. Morning departures are around 60% more expensive than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $486.

Reviews of the top 5 airlines serving from Boston to the Cayman Islands

 
Need help choosing which airline to fly with from Boston to the Cayman Islands? 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.
7.9
DeltaOverall score based on 8011 reviews
8.5Crew
7.9Comfort
7.3Food
7.9Entertainment
8.1Boarding
Airline reviews

The food is terrible. The staff is wonderful. Comfort is good.

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

Not great experience - we were super late boarding due to issues with aircraft. Then when we finally all got onboard and seated and they started taxiing out to the runway they just stopped then turned around and went back to the airport. Apparently the crew “ran out of time” to legally fly us. They mentioned that they were about 2 minutes away from taking off. I understand the rules and safety but kinda wonder why they would have bothered boarding us in the first place? Had to go all the way back and de plane and then wait in a HUGE line to get a hotel (this is somewhere around 2:30am) finally got to hotel by Uber (no shuttle after 20min so gave up) and they ended up putting us all back on the same aircraft at 10am next morning so got about 2.5 hours sleep. They did give us. $250 credit, but it was a São Paulo Brazil flight out of Dulles. The flight and everything was fine.

United overall experience is great these days. Airport experience was very organized. Staff on flight were great. App and information as good as it gets.

United have really come back. Airport and boarding process is clear and good, app and information also very good

They charged a fee for 1st bag checked. Others in same party were free.

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very bad! They kept delaying my flight and wouldn’t do anything about it

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

The only downside was my cell phone charger wouldn’t work in the charging port but everyone else’s would work in them all. My cell phone cable works fine in my hotel room in Frankfurt.

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Everything you need to know for your flight from Boston to the Cayman Islands

Information on your arrival and departure airports