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Cheap flights from Massachusetts to Caribbean from $65

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 2/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Spirit Airlines Logo
11:22 am - 2:43 pm
SJU
-
BOS
4h 21mnonstop
$142Spirit Airlines
Tue, Feb 10 - Sun, Feb 15
Spirit Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Spirit Airlines Logo
4:36 pm - 11:44 pm
SJU
-
BOS
8h 08m
1 stop
$143Spirit Airlines
Sat, Feb 7 - Thu, Feb 12
Multiple Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Multiple Airlines Logo
4:07 pm - 1:13 am
SJU
-
BOS
10h 06m
1 stop
$144Multiple Airlines
Sun, Feb 8 - Wed, Feb 18
Multiple Airlines Logo
3:18 pm - 8:24 pm
BOS
-
SJU
4h 06mnonstop
Multiple Airlines Logo
4:36 pm - 1:13 am
SJU
-
BOS
9h 37m
2 stops
$151Multiple Airlines
Mon, Feb 9 - Thu, Feb 12
Frontier Logo
7:55 pm - 12:46 am
BDL
-
SJU
3h 51mnonstop
Frontier Logo
10:57 am - 5:05 pm
SJU
-
BDL
7h 08m
1 stop
$195Frontier
Wed, Feb 18 - Thu, Feb 26
Frontier Logo
8:08 pm - 9:54 am
BDL
-
SJU
13h 46m
1 stop
Frontier Logo
11:59 pm - 4:05 am
SJU
-
BDL
4h 06mnonstop
$196Frontier
Sat, Apr 25 - Sat, May 2
JetBlue Logo
8:14 am - 1:20 pm
BOS
-
STT
4h 06mnonstop
JetBlue Logo
2:15 pm - 7:03 pm
STT
-
BOS
5h 48m
1 stop
$223JetBlue
Tue, Feb 24 - Fri, Mar 6
Delta Logo
8:55 am - 2:00 pm
BOS
-
STT
4h 05mnonstop
Delta Logo
4:15 pm - 1:09 am
STT
-
BOS
9h 54m
1 stop
$228Delta
Mon, Feb 23 - Wed, Mar 4
Delta Logo
5:35 am - 5:02 pm
BOS
-
NAS
11h 27m
1 stop
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
$304Delta
Mon, Feb 9 - Fri, Feb 13
JetBlue Logo
11:40 am - 3:22 pm
BOS
-
NAS
3h 42mnonstop
JetBlue Logo
6:25 pm - 9:48 pm
NAS
-
BOS
3h 23mnonstop
$319JetBlue
Mon, Feb 23 - Mon, Mar 2

Spirit Airlines flights from Massachusetts to Caribbean

Our best Spirit Airlines deals on Massachusetts to Caribbean flight tickets
Spirit Airlines
Feb 23
BOS8:01 pmBoston Logan Intl
4h 07m
SJU1:08 amSan Juan Luis Munoz Marin Intl
Feb 25
SJU11:52 amSan Juan Luis Munoz Marin Intl
13h 07m
1 stop
BOS11:59 pmBoston Logan Intl
$142
Spirit Airlines
Feb 7
BOS3:18 pmBoston Logan Intl
4h 06m
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Feb 12
SJU4:36 pmSan Juan Luis Munoz Marin Intl
8h 08m
1 stop
BOS11:44 pmBoston Logan Intl
$143
Spirit Airlines
Mar 4
BOS8:01 pmBoston Logan Intl
4h 07m
SJU1:08 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU10:52 amSan Juan Luis Munoz Marin Intl
13h 07m
1 stop
BOS11:59 pmBoston Logan Intl
$145

Frontier flights from Massachusetts to Caribbean

Our best Frontier deals on Massachusetts to Caribbean flight tickets
Frontier
Feb 7
BOS6:00 amBoston Logan Intl
10h 00m
1 stop
SJU5:00 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 19m
BOS9:19 amBoston Logan Intl
$150
Frontier
Feb 10
BOS6:00 amBoston Logan Intl
8h 06m
1 stop
SJU3:06 pmSan Juan Luis Munoz Marin Intl
Feb 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 19m
BOS9:19 amBoston Logan Intl
$155
Frontier
Feb 8
BOS6:00 amBoston Logan Intl
8h 12m
1 stop
SJU3:12 pmSan Juan Luis Munoz Marin Intl
Feb 13
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 19m
BOS9:19 amBoston Logan Intl
$163

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 January 26, 2026.
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

Tue 2/10

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sun 2/15

11:22 am-2:43 pm

Nonstop4h 21m

$142

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/7

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Thu 2/12

4:36 pm-11:44 pm

1 stop8h 08m

$143

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 2/8

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Wed 2/18

4:07 pm-1:13 am

1 stop10h 06m

$144

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 2/9

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Thu 2/12

4:36 pm-1:13 am

2 stops9h 37m

$151

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Wed 2/18

7:55 pm-12:46 am

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Thu 2/26

10:57 am-5:05 pm

1 stop7h 08m

$195

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 4/25

8:08 pm-9:54 am

1 stop13h 46m

San Juan Luis Munoz Marin Intl

Sat 5/2

11:59 pm-4:05 am

Nonstop4h 06m

$196

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 2/24

8:14 am-1:20 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

Fri 3/6

2:15 pm-7:03 pm

1 stop5h 48m

$223

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 2/23

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 3/4

4:15 pm-1:09 am

1 stop9h 54m

$228

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Mon 2/9

5:35 am-5:02 pm

1 stop11h 27m

Nassau Intl

Fri 2/13

2:40 pm-6:08 pm

Nonstop3h 28m

$304

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Mon 2/23

11:40 am-3:22 pm

Nonstop3h 42m

Nassau Intl

Mon 3/2

6:25 pm-9:48 pm

Nonstop3h 23m

$319

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 $254. 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 $264.

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 $301. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $341. 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 afternoon is the cheapest time of day to fly from Massachusetts to Caribbean when you can find flight prices for as low as $300. Flying to Caribbean in the afternoon 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 $334.

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 $271 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?

No. A direct flight is the cheapest option for a flight between Massachusetts to Caribbean.

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

$101

Fastest flight time

3h 23m

Direct flights

Every day

Airports in Caribbean

195 airports
The best one-way flight to Caribbean from Massachusetts in the past 72 hours is $101. The best round-trip flight deal from Massachusetts to Caribbean found on momondo in the last 72 hours is $203.
The fastest flight from Massachusetts to Caribbean takes 3h 23m
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 $76Free CancellationRating
5.7
3,058 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $79Free CancellationRating
6.3
8,379 reviews
Search Spirit Airlines flights
Air CanadaPriceFrom $129Free CancellationRating
7.1
10,656 reviews
Search Air Canada flights
DeltaPriceFrom $136Free CancellationRating
7.9
8,113 reviews
Search Delta flights
JetBluePriceFrom $140Free CancellationRating
7.2
2,892 reviews
Search JetBlue flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
9,200 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $179Free CancellationRating
7.6
1,558 reviews
Search Copa Airlines flights
ArajetPriceFrom $181Free CancellationRating
6.6
43 reviews
Search Arajet flights
American AirlinesPriceFrom $242Free CancellationRating
7.2
11,189 reviews
Search American Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,491 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.

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