What is the cheapest airline that flies from Massachusetts to Caribbean Islands?

United Airlines, Delta, and American Airlines are the most popular carriers operating from Massachusetts to Caribbean Islands

What airlines fly to Caribbean Islands?

JetBlue, Delta and American Airlines are the top three most popular airlines that fly to Caribbean Islands from Massachusetts according to our data. JetBlue is the first choice among our users, with 66% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 12 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How long is the flight from Massachusetts to Caribbean Islands?

The flight from Massachusetts to Caribbean Islands depends on which airports you’re departing and arriving from and whether or not you have a layover. If you fly from Boston (a popular airport in Massachusetts) to Madrid (the most popular airport in Caribbean Islands), then the flight time is 7h on average. If you fly from Provincetown (another popular airport in Massachusetts) to Madrid, then the average flight time is 11h 31m.

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

Prices for flights from Massachusetts to Caribbean Islands are refreshed on a daily basis.

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

As of December 2025, there are 13 operators available to choose from for flights from Massachusetts to Caribbean Islands.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Massachusetts to Caribbean Islands.

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

The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$84 Cheap Flights from Massachusetts to Caribbean Islands in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

3:18 pm - 8:24 pmBOS-SJU

4h 06mnonstop

6:10 am - 9:20 amSJU-BOS

4h 10mnonstop

$161Multiple Airlines

Find Deal

Fri, Jan 23 - Sun, Jan 25

11:55 am - 10:05 pmBOS-SJU

9h 10m1 stop

6:00 am - 2:38 pmSJU-BOS

9h 38m1 stop

$165Spirit Airlines

Find Deal

Mon, Jan 5 - Wed, Jan 14

4:30 pm - 2:39 amBDL-SJU

9h 09m1 stop

6:00 am - 9:15 amSJU-BDL

4h 15mnonstop

$179Frontier

Find Deal

Mon, Jan 5 - Fri, Jan 16

8:01 pm - 9:54 amBDL-SJU

12h 53m1 stop

12:45 pm - 3:53 pmSJU-BDL

4h 08mnonstop

$180Frontier

Find Deal

Sat, Jan 31 - Wed, Feb 11

8:55 am - 2:00 pmBOS-STT

4h 05mnonstop

2:32 pm - 5:53 pmSTT-BOS

4h 21mnonstop

$234Delta

Find Deal

Tue, Jan 20 - Fri, Jan 23

8:55 am - 2:00 pmBOS-STT

4h 05mnonstop

4:15 pm - 1:04 amSTT-BOS

9h 49m1 stop

$239Delta

Find Deal

Wed, Jan 21 - Wed, Jan 28

9:45 am - 1:46 pmBOS-STT

4h 01mnonstop

2:41 pm - 8:34 pmSTT-BOS

5h 53m1 stop

$242JetBlue

Find Deal

Thu, Mar 26 - Mon, Mar 30

6:05 am - 1:46 pmBOS-STT

6h 41m1 stop

4:47 pm - 11:05 pmSTT-BOS

7h 18m1 stop

$244American Airlines

Find Deal

Mon, Jan 19 - Fri, Jan 23

8:00 am - 1:05 pmBOS-STT

4h 05mnonstop

5:50 pm - 10:38 pmSTT-BOS

5h 48m1 stop

$254JetBlue

Find Deal

Thu, Jan 22 - Sat, Jan 31

6:00 am - 1:55 pmBOS-NAS

7h 55m2 stops

6:45 pm - 12:59 amNAS-BOS

6h 14m1 stop

$317American Airlines

Find Deal

Mon, Dec 15 - Mon, Dec 22

Frontier flights from Massachusetts to Caribbean Islands

Our best Frontier deals on Massachusetts to Caribbean Islands flight tickets

Frontier

Dec 12

BOS10:52 amBoston Logan Intl

11h 22m

1 stop

SJU11:14 pmSan Juan Luis Munoz Marin Intl

Dec 23

SJU8:00 amSan Juan Luis Munoz Marin Intl

4h 23m

BOS11:23 amBoston Logan Intl

$170

Find similar

Frontier

Dec 12

BOS10:52 amBoston Logan Intl

11h 22m

1 stop

SJU11:14 pmSan Juan Luis Munoz Marin Intl

Dec 25

SJU8:00 amSan Juan Luis Munoz Marin Intl

4h 23m

BOS11:23 amBoston Logan Intl

$172

Find similar

Frontier

Feb 26

BOS10:24 amBoston Logan Intl

4h 04m

SJU3:28 pmSan Juan Luis Munoz Marin Intl

Mar 5

SJU6:00 amSan Juan Luis Munoz Marin Intl

4h 23m

BOS9:23 amBoston Logan Intl

$175

Find similar

Spirit Airlines flights from Massachusetts to Caribbean Islands

Our best Spirit Airlines deals on Massachusetts to Caribbean Islands flight tickets

Spirit Airlines

Jan 11

BOS3:43 pmBoston Logan Intl

17h 04m

1 stop

SJU9:47 amSan Juan Luis Munoz Marin Intl

Jan 17

SJU4:40 pmSan Juan Luis Munoz Marin Intl

8h 17m

1 stop

BOS11:57 pmBoston Logan Intl

$167

Find similar

Spirit Airlines

Dec 10

BOS8:11 pmBoston Logan Intl

13h 22m

1 stop

SJU10:33 amSan Juan Luis Munoz Marin Intl

Dec 22

SJU3:15 pmSan Juan Luis Munoz Marin Intl

4h 24m

BOS6:39 pmBoston Logan Intl

$171

Find similar

Spirit Airlines

Feb 1

BOS3:18 pmBoston Logan Intl

4h 06m

SJU8:24 pmSan Juan Luis Munoz Marin Intl

Feb 9

SJU10:52 amSan Juan Luis Munoz Marin Intl

4h 20m

BOS2:12 pmBoston Logan Intl

$172

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 1/23

3:18 pm-8:24 pm

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Sun 1/25

6:10 am-9:20 am

Nonstop4h 10m

$161

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 1/5

11:55 am-10:05 pm

1 stop9h 10m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:00 am-2:38 pm

1 stop9h 38m

$165

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Mon 1/5

4:30 pm-2:39 am

1 stop9h 09m

San Juan Luis Munoz Marin Intl

Fri 1/16

6:00 am-9:15 am

Nonstop4h 15m

$179

HartfordSan Juan

BDL - SJU

BDLSJU

Hartford Bradley Intl

Sat 1/31

8:01 pm-9:54 am

1 stop12h 53m

San Juan Luis Munoz Marin Intl

Wed 2/11

12:45 pm-3:53 pm

Nonstop4h 08m

$180

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 1/20

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Fri 1/23

2:32 pm-5:53 pm

Nonstop4h 21m

$234

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Wed 1/21

8:55 am-2:00 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Wed 1/28

4:15 pm-1:04 am

1 stop9h 49m

$239

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 3/26

9:45 am-1:46 pm

Nonstop4h 01m

Saint Thomas Island Cyril E King

Mon 3/30

2:41 pm-8:34 pm

1 stop5h 53m

$242

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Mon 1/19

6:05 am-1:46 pm

1 stop6h 41m

Saint Thomas Island Cyril E King

Fri 1/23

4:47 pm-11:05 pm

1 stop7h 18m

$244

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Thu 1/22

8:00 am-1:05 pm

Nonstop4h 05m

Saint Thomas Island Cyril E King

Sat 1/31

5:50 pm-10:38 pm

1 stop5h 48m

$254

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Mon 12/15

6:00 am-1:55 pm

2 stops7h 55m

Nassau Intl

Mon 12/22

6:45 pm-12:59 am

1 stop6h 14m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Massachusetts to Caribbean Islands

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

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Massachusetts, with most prices found around $224. The month of March is another great option to travel to Caribbean Islands, with average flight prices from Massachusetts averaging around $264.

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

The cheapest day to depart from Massachusetts to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets 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 Islands.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the morning. momondo users have found flights departing from Massachusetts to Caribbean Islands in the morning for as low as $318. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets at noon because they tend to be around $343. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Massachusetts to Caribbean Islands flight route?

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

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

You are more likely to see cheaper flights to Caribbean Islands from Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $300 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Massachusetts for as low as $263 on momondo.

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

There are 4 cabin classes available to choose from on Massachusetts to Caribbean Islands 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 Islands flights?

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

Cheap Massachusetts to Caribbean Islands flight deals and tips

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

Fastest flight time	3h 30m
Direct flights	Every day
Airports in Caribbean Islands	3 airports

The fastest flight from Massachusetts to Caribbean Islands takes 3h 30m

Direct flights go from Massachusetts to Caribbean Islands every day.

There are 3 airports near Caribbean Islands: Nassau Intl (NAS), Providenciales (PLS), Santiago de los Caballeros (STI)

Search flight deals

When did momondo last update prices for flights from Massachusetts to Caribbean Islands?
Prices for flights from Massachusetts to Caribbean Islands are refreshed on a daily basis.
How many operators does momondo search for flights from Massachusetts to Caribbean Islands?
As of December 2025, there are 13 operators available to choose from for flights from Massachusetts to Caribbean Islands.
How old do you have to be to fly from Massachusetts to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Massachusetts to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The necessary travel and health documents for your Caribbean Islands trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Massachusetts to Caribbean Islands?
momondo data reveals that the most frequently booked plane model on the route from Massachusetts to Caribbean Islands is Airbus A321neo, representing 13.26% of all bookings. The subsequent popular models are Airbus A220-300 at 11.64%, Airbus A321-100/200 at 9.71%, and Airbus A320-100/200 at 9.37%.

Best airlines flying from Massachusetts to Caribbean Islands

Compare and see reviews for airlines that fly from Massachusetts to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $87	Free Cancellation	Rating 5.8 3,094 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $99	Free Cancellation	Rating 6.3 8,156 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $136	Free Cancellation	Rating 7.2 2,901 reviews	Search JetBlue flights
Air Canada	PriceFrom $141	Free Cancellation	Rating 7.1 10,496 reviews	Search Air Canada flights
Delta	PriceFrom $148	Free Cancellation	Rating 7.9 8,011 reviews	Search Delta flights
Copa Airlines	PriceFrom $180	Free Cancellation	Rating 7.6 1,559 reviews	Search Copa Airlines flights
United Airlines	PriceFrom $194	Free Cancellation	Rating 7.4 9,063 reviews	Search United Airlines flights
Arajet	PriceFrom $230	Free Cancellation	Rating 6.9 37 reviews	Search Arajet flights
American Airlines	PriceFrom $288	Free Cancellation	Rating 7.2 11,045 reviews	Search American Airlines flights
Avianca	PriceFrom $356	Free Cancellation	Rating 6.6 2,478 reviews	Search Avianca flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Massachusetts to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Massachusetts with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Massachusetts.

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

Yes. momondo can track prices for Massachusetts to Caribbean Islands 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 Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Popular cities in Caribbean Islands

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Cheap flights from Massachusetts to Caribbean Islands from $84

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 Islands departing on 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Massachusetts to Caribbean Islands

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Massachusetts to Caribbean Islands

Our best Frontier deals on Massachusetts to Caribbean Islands flight tickets

Spirit Airlines flights from Massachusetts to Caribbean Islands

Our best Spirit Airlines deals on Massachusetts to Caribbean Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Massachusetts to Caribbean Islands that are best for you.

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Massachusetts to Caribbean Islands

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 Islands?

The month of January is, on average, the cheapest month to fly to Caribbean Islands from Massachusetts, with most prices found around $224. The month of March is another great option to travel to Caribbean Islands, with average flight prices from Massachusetts averaging around $264.

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

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

What is the cheapest Massachusetts to Caribbean Islands flight route?

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

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

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

There are 4 cabin classes available to choose from on Massachusetts to Caribbean Islands 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 Islands flights?

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

What is the cheapest airline that flies from Massachusetts to Caribbean Islands?

United Airlines, Delta, and American Airlines are the most popular carriers operating from Massachusetts to Caribbean Islands

What airlines fly to Caribbean Islands?

How many flights depart from Massachusetts to Caribbean Islands on average per day?

As of December 2025, there are 16 flights per day flying from Massachusetts to Caribbean Islands. The most common time of day flights depart is 10:00PM, with 50% of flights taking off in the evening.

How many flights depart from Massachusetts to Caribbean Islands on average per week?

The number of flights available between Massachusetts and Caribbean Islands is 113 per week as of December 2025. The most frequent departure day is Tue, with 19% of weekly flights leaving on this day.

How long is the flight from Massachusetts to Caribbean Islands?

Cheap Massachusetts to Caribbean Islands flight deals and tips

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

Fastest flight time

Direct flights

Airports in Caribbean Islands

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

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

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

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

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

Best airlines flying from Massachusetts to Caribbean Islands

Compare and see reviews for airlines that fly from Massachusetts to Caribbean Islands with momondo

Why use momondo?

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

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

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

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

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo