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Cheap flights from Massachusetts to Caribbean from $66

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 9/2. 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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Find the cheapest flights from Massachusetts to Caribbean

Cheap round-trip flights

Spirit Airlines Logo
3:37 pm - 11:57 pmBOS-SJU
8h 20m1 stop
Spirit Airlines Logo
6:44 am - 1:48 pmSJU-BOS
7h 04m1 stop
$139Spirit Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Spirit Airlines Logo
10:34 am - 11:57 pmBOS-SJU
13h 23m1 stop
Spirit Airlines Logo
6:44 am - 1:48 pmSJU-BOS
7h 04m1 stop
$141Spirit Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Logo
12:20 pm - 8:56 pmBOS-SJU
8h 36m1 stop
Logo
12:28 am - 8:43 amSJU-BOS
8h 15m1 stop
$205
Find Deal
Sat, Sep 6 - Sat, Sep 13
Logo
11:18 am - 2:50 amBOS-SJU
15h 32m1 stop
Logo
6:44 am - 1:48 pmSJU-BOS
7h 04m1 stop
$206
Find Deal
Mon, Sep 1 - Wed, Sep 10
JetBlue Logo
5:20 pm - 9:10 pmBDL-SJU
3h 50mnonstop
JetBlue Logo
6:33 pm - 10:29 pmSJU-BDL
3h 56mnonstop
$242JetBlue
Find Deal
Fri, Oct 3 - Fri, Oct 10
JetBlue Logo
7:50 pm - 12:39 amBDL-SJU
3h 49mnonstop
JetBlue Logo
5:30 am - 8:40 amSJU-BDL
4h 10mnonstop
$244JetBlue
Find Deal
Sat, Jan 17 - Sat, Jan 24
Frontier Logo
9:09 pm - 1:04 amBDL-SJU
3h 55mnonstop
Frontier Logo
11:17 am - 3:17 pmSJU-BDL
4h 00mnonstop
$248Frontier
Find Deal
Sat, Aug 23 - Wed, Aug 27
Frontier Logo
9:09 pm - 1:04 amBDL-SJU
3h 55mnonstop
Frontier Logo
11:17 am - 3:17 pmSJU-BDL
4h 00mnonstop
$254Frontier
Find Deal
Sun, Aug 24 - Wed, Aug 27
Arajet Logo
7:30 pm - 12:45 amBOS-SDQ
4h 15mnonstop
Arajet Logo
6:30 am - 9:45 amSDQ-BOS
4h 15mnonstop
$296Arajet
Find Deal
Thu, Nov 27 - Fri, Dec 12
Arajet Logo
11:15 am - 4:30 pmBOS-SDQ
4h 15mnonstop
Arajet Logo
6:30 am - 9:45 amSDQ-BOS
4h 15mnonstop
$357Arajet
Find Deal
Wed, Jan 7 - Wed, Feb 18

Spirit Airlines flights from Massachusetts to Caribbean

Our best Spirit Airlines deals on Massachusetts to Caribbean flight tickets
Spirit Airlines
Sep 2
BOS3:37 pmBoston Logan Intl
8h 20m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU6:44 amSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
BOS1:48 pmBoston Logan Intl
$139
Find similar
Spirit Airlines
Sep 2
BOS10:34 amBoston Logan Intl
13h 23m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU6:44 amSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
BOS1:48 pmBoston Logan Intl
$141
Find similar
Spirit Airlines
Sep 2
BOS10:34 amBoston Logan Intl
13h 23m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Sep 10
SJU6:44 amSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
BOS1:48 pmBoston Logan Intl
$143
Find similar

Frontier flights from Massachusetts to Caribbean

Our best Frontier deals on Massachusetts to Caribbean flight tickets
Frontier
Aug 23
BDL9:09 pmHartford Bradley Intl
3h 55m
SJU1:04 amSan Juan Luis Munoz Marin Intl
Aug 27
SJU11:17 amSan Juan Luis Munoz Marin Intl
4h 00m
BDL3:17 pmHartford Bradley Intl
$248
Find similar
Frontier
Aug 24
BDL9:09 pmHartford Bradley Intl
3h 55m
SJU1:04 amSan Juan Luis Munoz Marin Intl
Aug 27
SJU11:17 amSan Juan Luis Munoz Marin Intl
4h 00m
BDL3:17 pmHartford Bradley Intl
$254
Find similar
Frontier
Aug 18
BDL10:47 amHartford Bradley Intl
3h 55m
SJU2:42 pmSan Juan Luis Munoz Marin Intl
Aug 27
SJU11:17 amSan Juan Luis Munoz Marin Intl
4h 00m
BDL3:17 pmHartford Bradley Intl
$261
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 August 4, 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

Tue 9/2

3:37 pm-11:57 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 9/9

6:44 am-1:48 pm

1 stop7h 04m

$139

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 9/2

10:34 am-11:57 pm

1 stop13h 23m

San Juan Luis Munoz Marin Intl

Tue 9/9

6:44 am-1:48 pm

1 stop7h 04m

$141

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 9/6

12:20 pm-8:56 pm

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Sat 9/13

12:28 am-8:43 am

1 stop8h 15m

$205

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 9/1

11:18 am-2:50 am

1 stop15h 32m

San Juan Luis Munoz Marin Intl

Wed 9/10

6:44 am-1:48 pm

1 stop7h 04m

$206

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Fri 10/3

5:20 pm-9:10 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 10/10

6:33 pm-10:29 pm

Nonstop3h 56m

$242

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 1/17

7:50 pm-12:39 am

Nonstop3h 49m

San Juan Luis Munoz Marin Intl

Sat 1/24

5:30 am-8:40 am

Nonstop4h 10m

$244

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 8/23

9:09 pm-1:04 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Wed 8/27

11:17 am-3:17 pm

Nonstop4h 00m

$248

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sun 8/24

9:09 pm-1:04 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Wed 8/27

11:17 am-3:17 pm

Nonstop4h 00m

$254

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Thu 11/27

7:30 pm-12:45 am

Nonstop4h 15m

Santo Domingo Las Americas

Fri 12/12

6:30 am-9:45 am

Nonstop4h 15m

$296

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Wed 1/7

11:15 am-4:30 pm

Nonstop4h 15m

Santo Domingo Las Americas

Wed 2/18

6:30 am-9:45 am

Nonstop4h 15m

$357

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, September 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 $177. If you don’t want to visit Caribbean in September, then you should wait until October to fly from Massachusetts, when ticket prices are also cheap, with an average price of $220.

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 $289. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $327. 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 $294. Flying to Caribbean in the morning is an ideal time because this is during off-peak travel hours. Flights in the evening are often more expensive with an average ticket price of $339.

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 $272 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 $223 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

$66

Fastest flight time

3h 48m

Direct flights

Every day

Airports in Caribbean

8 airports
The best one-way flight to Caribbean from Massachusetts in the past 72 hours is $66. The best round-trip flight deal from Massachusetts to Caribbean found on momondo in the last 72 hours is $139.
The fastest flight from Massachusetts to Caribbean takes 3h 48m
Direct flights go from Massachusetts to Caribbean every day.
There are 8 airports near Caribbean: Santo Domingo Las Americas (SDQ), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Providenciales (PLS), Simpson Bay Princess Juliana (SXM), Santiago de los Caballeros (STI), San Juan Luis Munoz Marin Intl (SJU)
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  • 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 $80Free CancellationRating
5.8
3,231 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $97Free CancellationRating
6.3
8,053 reviews
Search Spirit Airlines flights
JetBluePriceFrom $136Free CancellationRating
7.2
2,915 reviews
Search JetBlue flights
DeltaPriceFrom $140Free CancellationRating
8.0
7,986 reviews
Search Delta flights
ArajetPriceFrom $171Free CancellationRating
6.9
33 reviews
Search Arajet flights
Air CanadaPriceFrom $188Free CancellationRating
7.1
9,874 reviews
Search Air Canada flights
United AirlinesPriceFrom $204Free CancellationRating
7.4
8,909 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $255Free CancellationRating
7.5
1,496 reviews
Search Copa Airlines flights
American AirlinesPriceFrom $288Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
AviancaPriceFrom $292Free CancellationRating
6.7
2,392 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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Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo
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Flights to Santiago de los Caballerosfrom $193