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Cheap flights from Massachusetts to Caribbean from $77

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Caribbean departing on 1/17. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Massachusetts to Caribbean

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:08 am - 1:24 am
BOS
-
SJU
16h 16m1 stop
Frontier Logo
4:35 pm - 1:13 am
SJU
-
BOS
9h 38m1 stop
$149Frontier
Mon, Jan 5 - Wed, Jan 14
Multiple Airlines Logo
6:00 am - 5:00 pm
BOS
-
SJU
10h 00m1 stop
Multiple Airlines Logo
6:15 am - 9:25 am
SJU
-
BOS
4h 10mnonstop
$151Multiple Airlines
Sat, Jan 24 - Tue, Jan 27
Frontier Logo
10:24 am - 3:28 pm
BOS
-
SJU
4h 04mnonstop
Frontier Logo
3:06 pm - 1:04 am
SJU
-
BOS
9h 58m1 stop
$152Frontier
Sun, Mar 1 - Tue, Mar 10
Multiple Airlines Logo
6:00 am - 3:27 pm
BOS
-
SJU
8h 27m1 stop
Multiple Airlines Logo
10:52 am - 2:12 pm
SJU
-
BOS
4h 20mnonstop
$153Multiple Airlines
Sat, Jan 17 - Fri, Jan 23
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Spirit Airlines Logo
6:00 am - 2:38 pm
SJU
-
BOS
9h 38m1 stop
$156Spirit Airlines
Fri, Jan 9 - Tue, Jan 13
Spirit Airlines Logo
3:43 pm - 11:33 pm
BOS
-
SJU
6h 50m1 stop
Spirit Airlines Logo
6:00 am - 2:38 pm
SJU
-
BOS
9h 38m1 stop
$159Spirit Airlines
Tue, Jan 20 - Fri, Jan 23
JetBlue Logo
8:00 am - 1:05 pm
BOS
-
STT
4h 05mnonstop
JetBlue Logo
2:00 pm - 6:49 pm
STT
-
BOS
5h 49m1 stop
$234JetBlue
Tue, Jan 20 - Fri, Jan 30
JetBlue Logo
9:45 am - 1:46 pm
BOS
-
STT
4h 01mnonstop
JetBlue Logo
2:41 pm - 8:34 pm
STT
-
BOS
5h 53m1 stop
$235JetBlue
Tue, Mar 17 - Fri, Mar 20
Delta Logo
6:00 am - 1:22 pm
BOS
-
STT
6h 22m1 stop
Delta Logo
2:32 pm - 5:53 pm
STT
-
BOS
4h 21mnonstop
$239Delta
Wed, Jan 21 - Fri, Jan 30
Delta Logo
6:55 am - 2:51 pm
BOS
-
STT
7h 56m1 stop
Delta Logo
3:56 pm - 10:54 pm
STT
-
BOS
6h 58m1 stop
$243Delta
Tue, Mar 10 - Wed, Mar 18

Spirit Airlines flights from Massachusetts to Caribbean

Our best Spirit Airlines deals on Massachusetts to Caribbean flight tickets
Spirit Airlines
Jan 11
BOS3:18 pmBoston Logan Intl
4h 06m
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU6:00 amSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
BOS2:38 pmBoston Logan Intl
$156
Find similar
Spirit Airlines
Jan 20
BOS5:34 amBoston Logan Intl
9h 01m
1 stop
SJU3:35 pmSan Juan Luis Munoz Marin Intl
Mar 3
SJU10:52 amSan Juan Luis Munoz Marin Intl
4h 20m
BOS2:12 pmBoston Logan Intl
$164
Find similar
Spirit Airlines
Feb 3
BOS3:18 pmBoston Logan Intl
4h 06m
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Feb 4
SJU4:40 pmSan Juan Luis Munoz Marin Intl
8h 17m
1 stop
BOS11:57 pmBoston Logan Intl
$166
Find similar

Frontier flights from Massachusetts to Caribbean

Our best Frontier deals on Massachusetts to Caribbean flight tickets
Frontier
Jan 5
BOS8:08 amBoston Logan Intl
16h 16m
1 stop
SJU1:24 amSan Juan Luis Munoz Marin Intl
Jan 14
SJU4:35 pmSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
BOS1:13 amBoston Logan Intl
$149
Find similar
Frontier
Mar 1
BOS10:24 amBoston Logan Intl
4h 04m
SJU3:28 pmSan Juan Luis Munoz Marin Intl
Mar 10
SJU3:06 pmSan Juan Luis Munoz Marin Intl
9h 58m
1 stop
BOS1:04 amBoston Logan Intl
$152
Find similar
Frontier
Jan 8
BOS12:31 pmBoston Logan Intl
3h 59m
SJU5:30 pmSan Juan Luis Munoz Marin Intl
Jan 17
SJU4:35 pmSan Juan Luis Munoz Marin Intl
9h 38m
1 stop
BOS1:13 amBoston Logan Intl
$153
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Massachusetts to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 11, 2025.
Use the filters below to find and compare flights from Massachusetts to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 1/5

8:08 am-1:24 am

1 stop16h 16m

San Juan Luis Munoz Marin Intl

Wed 1/14

4:35 pm-1:13 am

1 stop9h 38m

$149

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/24

6:00 am-5:00 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:15 am-9:25 am

Nonstop4h 10m

$151

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 3/1

10:24 am-3:28 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Tue 3/10

3:06 pm-1:04 am

1 stop9h 58m

$152

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/17

6:00 am-3:27 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Fri 1/23

10:52 am-2:12 pm

Nonstop4h 20m

$153

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 1/9

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 1/13

6:00 am-2:38 pm

1 stop9h 38m

$156

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 1/20

3:43 pm-11:33 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:00 am-2:38 pm

1 stop9h 38m

$159

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/20

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 1/30

2:00 pm-6:49 pm

1 stop5h 49m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/17

9:45 am-1:46 pm

Nonstop4h 01m

Saint Thomas Island Cyril E King

Fri 3/20

2:41 pm-8:34 pm

1 stop5h 53m

$235

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 1/21

6:00 am-1:22 pm

1 stop6h 22m

Saint Thomas Island Cyril E King

Fri 1/30

2:32 pm-5:53 pm

Nonstop4h 21m

$239

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 3/10

6:55 am-2:51 pm

1 stop7h 56m

Saint Thomas Island Cyril E King

Wed 3/18

3:56 pm-10:54 pm

1 stop6h 58m

$243

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Massachusetts to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean?

In general, January is the cheapest month to fly from Massachusetts to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $243. If you don’t want to visit Caribbean in January, then you should wait until March to fly from Massachusetts, when ticket prices are also cheap, with an average price of $262.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Massachusetts to Caribbean is on a Monday when prices can be found for as low as $300. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $343. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the morning is the cheapest time of day to fly from Massachusetts to Caribbean when you can find flight prices for as low as $320. Flying to Caribbean in the morning is an ideal time because this is during off-peak travel hours. Flights at noon are often more expensive with an average ticket price of $341.

What is the cheapest Massachusetts to Caribbean flight route?

Fly from Boston Logan Intl to San Juan Luis Munoz Marin Intl for the best Massachusetts - Caribbean flight prices

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $305 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Massachusetts for as low as $268 on momondo.

What cabin class options are available on Massachusetts to Caribbean flights?

There are 4 cabin classes available to choose from on Massachusetts to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Massachusetts to Caribbean flights?

You could potentially save up to 43% on your flight if you consider stops on a Massachusetts to Caribbean flight.

Cheap Massachusetts to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Massachusetts to Caribbean

Best Price Found

$136

Fastest flight time

3h 22m

Direct flights

Every day

Airports in Caribbean

195 airports
The best one-way flight to Caribbean from Massachusetts in the past 72 hours is $136. The best round-trip flight deal from Massachusetts to Caribbean found on momondo in the last 72 hours is $260.
The fastest flight from Massachusetts to Caribbean takes 3h 22m
Direct flights go from Massachusetts to Caribbean every day.
There are 195 airports in Caribbean. From Massachusetts there are direct flights to Nassau Intl (NAS), Providenciales (PLS).
Search flight deals

  • When did momondo last update prices for flights from Massachusetts to Caribbean?

    Prices for flights from Massachusetts to Caribbean refresh daily.

  • How many operators does momondo search for flights from Massachusetts to Caribbean?

  • How old do you have to be to fly from Massachusetts to Caribbean?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts to Caribbean.

  • What documentation or ID do you need to fly to Caribbean?

    The required travel and health documents for your Caribbean trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Massachusetts to Caribbean?

Best airlines flying from Massachusetts to Caribbean

Compare and see reviews for airlines that fly from Massachusetts to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $87Free CancellationRating
5.8
3,084 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $99Free CancellationRating
6.3
8,180 reviews
Search Spirit Airlines flights
JetBluePriceFrom $136Free CancellationRating
7.2
2,899 reviews
Search JetBlue flights
Air CanadaPriceFrom $141Free CancellationRating
7.1
10,517 reviews
Search Air Canada flights
DeltaPriceFrom $149Free CancellationRating
7.9
8,007 reviews
Search Delta flights
Copa AirlinesPriceFrom $180Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $190Free CancellationRating
7.4
9,094 reviews
Search United Airlines flights
ArajetPriceFrom $208Free CancellationRating
6.8
38 reviews
Search Arajet flights
American AirlinesPriceFrom $288Free CancellationRating
7.2
11,049 reviews
Search American Airlines flights
AviancaPriceFrom $356Free CancellationRating
6.6
2,480 reviews
Search Avianca flights

Why use momondo?

Why should I use momondo to find a flight deal from Massachusetts to Caribbean?

Finding the right flight to Caribbean from Massachusetts is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean quick and easy, saving you time and money.

Can I find flights from Massachusetts to Caribbean with flexible booking policies on momondo?

Yes. All flights to Caribbean from Massachusetts on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Massachusetts to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Massachusetts to Caribbean.

I’m not ready to book a flight from Massachusetts to Caribbean right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Massachusetts to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Caribbean trip

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Find better results for your trip to Caribbean

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