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Cheap flights from Boston to Caribbean from $56

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Caribbean departing on 2/21. 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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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
4:31 pm - 11:44 pm
SJU
-
BOS
8h 13m
1 stop
$143Spirit Airlines
Sat, Feb 7 - Fri, Feb 13
Spirit Airlines Logo
3:43 pm - 11:33 pm
BOS
-
SJU
6h 50m
1 stop
Spirit Airlines Logo
11:22 am - 2:43 pm
SJU
-
BOS
4h 21mnonstop
$144Spirit Airlines
Sat, Feb 7 - Sat, Feb 14
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
American Airlines Logo
5:30 pm - 11:29 am
BOS
-
SXM
17h 59m
2 stops
American Airlines Logo
3:32 pm - 8:26 am
SXM
-
BOS
16h 54m
2 stops
$319American Airlines
Sat, Apr 4 - Sat, Apr 18
JetBlue Logo
7:00 am - 10:40 am
BOS
-
NAS
3h 40mnonstop
JetBlue Logo
11:55 am - 3:18 pm
NAS
-
BOS
3h 23mnonstop
$320JetBlue
Thu, Mar 12 - Tue, Mar 17
Delta Logo
9:25 am - 1:07 pm
BOS
-
NAS
3h 42mnonstop
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
$321Delta
Mon, Feb 23 - Mon, Mar 2
American Airlines Logo
5:40 am - 1:21 pm
BOS
-
SXM
7h 41m
1 stop
American Airlines Logo
4:36 pm - 7:35 am
SXM
-
BOS
14h 59m
2 stops
$324American Airlines
Wed, May 20 - Wed, May 27
Delta Logo
6:00 am - 11:50 am
BOS
-
NAS
5h 50m
1 stop
Delta Logo
2:40 pm - 6:08 pm
NAS
-
BOS
3h 28mnonstop
$326Delta
Mon, Feb 23 - Wed, Mar 4
Frontier Logo
6:00 am - 3:38 pm
BOS
-
PLS
9h 38m
1 stop
Frontier Logo
4:50 pm - 9:06 am
PLS
-
BOS
16h 16m
2 stops
$347Frontier
Sat, Feb 7 - Sat, Feb 14

Spirit Airlines flights from Boston to Caribbean

Our best Spirit Airlines deals on Boston to Caribbean flight tickets
Spirit Airlines
Feb 10
BOS3:18 pmBoston Logan Intl
4h 06m
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Feb 15
SJU11:22 amSan Juan Luis Munoz Marin Intl
4h 21m
BOS2:43 pmBoston Logan Intl
$142
Spirit Airlines
Feb 7
BOS3:18 pmBoston Logan Intl
4h 06m
SJU8:24 pmSan Juan Luis Munoz Marin Intl
Feb 13
SJU4:31 pmSan Juan Luis Munoz Marin Intl
8h 13m
1 stop
BOS11:44 pmBoston Logan Intl
$143
Spirit Airlines
Feb 7
BOS3:43 pmBoston Logan Intl
6h 50m
1 stop
SJU11:33 pmSan Juan Luis Munoz Marin Intl
Feb 14
SJU11:22 amSan Juan Luis Munoz Marin Intl
4h 21m
BOS2:43 pmBoston Logan Intl
$144

Frontier flights from Boston to Caribbean

Our best Frontier deals on Boston 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 26
BOS10:01 amBoston Logan Intl
13h 40m
1 stop
SJU12:41 amSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 19m
BOS9:19 amBoston Logan Intl
$155
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
$156

momondo Fare Finder

 
Customize your flight search to find flights from Boston 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 28, 2026.
Use the filters below to find and compare flights from Boston 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

Fri 2/13

4:31 pm-11:44 pm

1 stop8h 13m

$143

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 2/7

3:43 pm-11:33 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Sat 2/14

11:22 am-2:43 pm

Nonstop4h 21m

$144

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

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 4/4

5:30 pm-11:29 am

2 stops17h 59m

Simpson Bay Princess Juliana

Sat 4/18

3:32 pm-8:26 am

2 stops16h 54m

$319

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Thu 3/12

7:00 am-10:40 am

Nonstop3h 40m

Nassau Intl

Tue 3/17

11:55 am-3:18 pm

Nonstop3h 23m

$320

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Mon 2/23

9:25 am-1:07 pm

Nonstop3h 42m

Nassau Intl

Mon 3/2

2:40 pm-6:08 pm

Nonstop3h 28m

$321

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 5/20

5:40 am-1:21 pm

1 stop7h 41m

Simpson Bay Princess Juliana

Wed 5/27

4:36 pm-7:35 am

2 stops14h 59m

$324

BostonNassau

BOS - NAS

BOSNAS

Boston Logan Intl

Mon 2/23

6:00 am-11:50 am

1 stop5h 50m

Nassau Intl

Wed 3/4

2:40 pm-6:08 pm

Nonstop3h 28m

$326

BostonProvidenciales

BOS - PLS

BOSPLS

Boston Logan Intl

Sat 2/7

6:00 am-3:38 pm

1 stop9h 38m

Providenciales

Sat 2/14

4:50 pm-9:06 am

2 stops16h 16m

$347

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 Boston 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 Boston 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 Boston, 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 Boston 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 Boston to Caribbean when you can find flight prices for as low as $290. 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 Boston Logan Intl to Caribbean flight route?

Fly from Boston Logan Intl to San Juan Luis Munoz Marin Intl for the best Boston Logan Intl - 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 Boston 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 Boston for as low as $271 on momondo.

What cabin class options are available on Boston Logan Intl to Caribbean flights?

There are 4 cabin classes available to choose from on Boston Logan Intl 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 Boston to Caribbean flights?

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

Cheap Boston to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston 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 Boston in the past 72 hours is $101. The best round-trip flight deal from Boston to Caribbean found on momondo in the last 72 hours is $203.
The fastest flight from Boston to Caribbean takes 3h 23m
Direct flights go from Boston to Caribbean every day.
There are 195 airports in Caribbean. From Boston there are direct flights to Nassau Intl (NAS), Providenciales (PLS).
Search flight deals

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Caribbean?

    Prices for flights from Boston Logan Intl Airport to Caribbean are refreshed on a daily basis.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Caribbean?

  • How old do you have to be to fly from Boston Logan Intl Airport to Caribbean?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Boston Logan Intl Airport 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 Boston to Caribbean?

Best airlines flying from Boston to Caribbean

Compare and see reviews for airlines that fly from Boston to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $76Free CancellationRating
5.7
3,056 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $79Free CancellationRating
6.3
8,393 reviews
Search Spirit Airlines flights
Air CanadaPriceFrom $129Free CancellationRating
7.1
10,667 reviews
Search Air Canada flights
DeltaPriceFrom $136Free CancellationRating
7.9
8,128 reviews
Search Delta flights
JetBluePriceFrom $140Free CancellationRating
7.2
2,892 reviews
Search JetBlue flights
United AirlinesPriceFrom $177Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
Copa AirlinesPriceFrom $179Free CancellationRating
7.5
1,560 reviews
Search Copa Airlines flights
ArajetPriceFrom $181Free CancellationRating
6.6
43 reviews
Search Arajet flights
American AirlinesPriceFrom $242Free CancellationRating
7.2
11,205 reviews
Search American Airlines flights
AviancaPriceFrom $249Free CancellationRating
6.6
2,490 reviews
Search Avianca flights

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Boston to Caribbean for you.

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

Flights from Boston to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Boston 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 Boston to Caribbean.

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

Of course. momondo tracks the price of Boston to Caribbean flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Caribbean trip

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