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Cheap flights from Boston to Caribbean from $99

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 12/8. 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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Cheap round-trip flights

Spirit Airlines Logo
11:13 am - 4:07 pmBOS-SJU
3h 54mnonstop
Spirit Airlines Logo
5:27 pm - 8:34 pmSJU-BOS
4h 07mnonstop
$176Spirit Airlines
Find Deal
mar., févr. 3 - mar., févr. 10
Spirit Airlines Logo
11:13 am - 4:07 pmBOS-SJU
3h 54mnonstop
Spirit Airlines Logo
5:27 pm - 8:34 pmSJU-BOS
4h 07mnonstop
$184Spirit Airlines
Find Deal
sam., janv. 31 - sam., févr. 7
Frontier Logo
10:53 am - 9:56 amBOS-SJU
23h 03m2 stops
Frontier Logo
12:28 am - 8:43 amSJU-BOS
8h 15m1 stop
$227Frontier
Find Deal
ven., oct. 3 - sam., oct. 4
Frontier Logo
10:53 am - 9:56 amBOS-SJU
23h 03m2 stops
Frontier Logo
12:28 am - 8:43 amSJU-BOS
8h 15m1 stop
$233Frontier
Find Deal
lun., sept. 29 - mer., oct. 1
American Airlines Logo
5:47 am - 4:00 pmBOS-STT
10h 13m1 stop
American Airlines Logo
5:10 pm - 8:22 amSTT-BOS
15h 12m2 stops
$311American Airlines
Find Deal
sam., sept. 27 - sam., oct. 4
Delta Logo
8:40 am - 1:46 pmBOS-STT
4h 06mnonstop
Delta Logo
2:59 pm - 6:20 pmSTT-BOS
4h 21mnonstop
$330Delta
Find Deal
dim., janv. 18 - ven., janv. 23
JetBlue Logo
7:40 am - 1:35 pmBOS-STT
5h 55m1 stop
JetBlue Logo
2:04 pm - 7:48 pmSTT-BOS
5h 44m1 stop
$331JetBlue
Find Deal
mar., oct. 28 - sam., nov. 1
Delta Logo
5:00 pm - 12:27 amBOS-SDQ
7h 27m1 stop
Delta Logo
6:05 am - 6:55 pmSDQ-BOS
12h 50m1 stop
$331Delta
Find Deal
lun., oct. 6 - mar., oct. 21
JetBlue Logo
8:00 am - 2:58 pmBOS-PUJ
6h 58m1 stop
JetBlue Logo
12:35 pm - 5:04 pmPUJ-BOS
4h 29mnonstop
$339JetBlue
Find Deal
mar., oct. 21 - mer., oct. 22
American Airlines Logo
6:00 am - 12:05 pmBOS-PLS
6h 05m1 stop
American Airlines Logo
1:25 pm - 11:00 pmPLS-BOS
9h 35m1 stop
$348American Airlines
Find Deal
sam., oct. 18 - jeu., oct. 23

Frontier flights from Boston to Caribbean

Our best Frontier deals on Boston to Caribbean flight tickets
Frontier
Oct 3
BOS10:53 amBoston Logan Intl
23h 03m
2 stops
SJU9:56 amSan Juan Luis Munoz Marin Intl
Oct 4
SJU12:28 amSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
BOS8:43 amBoston Logan Intl
$227
Find similar
Frontier
Sep 25
BOS10:13 amBoston Logan Intl
29h 09m
1 stop
SJU3:22 pmSan Juan Luis Munoz Marin Intl
Sep 27
SJU12:28 amSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
BOS8:43 amBoston Logan Intl
$231
Find similar
Frontier
Sep 29
BOS10:53 amBoston Logan Intl
23h 03m
2 stops
SJU9:56 amSan Juan Luis Munoz Marin Intl
Oct 1
SJU12:28 amSan Juan Luis Munoz Marin Intl
8h 15m
1 stop
BOS8:43 amBoston Logan Intl
$233
Find similar

Spirit Airlines flights from Boston to Caribbean

Our best Spirit Airlines deals on Boston to Caribbean flight tickets
Spirit Airlines
Feb 3
BOS11:13 amBoston Logan Intl
3h 54m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Feb 10
SJU5:27 pmSan Juan Luis Munoz Marin Intl
4h 07m
BOS8:34 pmBoston Logan Intl
$176
Find similar
Spirit Airlines
Jan 31
BOS11:13 amBoston Logan Intl
3h 54m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Feb 7
SJU5:27 pmSan Juan Luis Munoz Marin Intl
4h 07m
BOS8:34 pmBoston Logan Intl
$184
Find similar
Spirit Airlines
Feb 4
BOS11:13 amBoston Logan Intl
3h 54m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Feb 10
SJU5:27 pmSan Juan Luis Munoz Marin Intl
4h 07m
BOS8:34 pmBoston Logan Intl
$185
Find similar

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 septembre 16, 2025.
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

mar. 2/3

11:13 am-4:07 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

mar. 2/10

5:27 pm-8:34 pm

Nonstop4h 07m

$176

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

sam. 1/31

11:13 am-4:07 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sam. 2/7

5:27 pm-8:34 pm

Nonstop4h 07m

$184

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

ven. 10/3

10:53 am-9:56 am

2 stops23h 03m

San Juan Luis Munoz Marin Intl

sam. 10/4

12:28 am-8:43 am

1 stop8h 15m

$227

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

lun. 9/29

10:53 am-9:56 am

2 stops23h 03m

San Juan Luis Munoz Marin Intl

mer. 10/1

12:28 am-8:43 am

1 stop8h 15m

$233

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

sam. 9/27

5:47 am-4:00 pm

1 stop10h 13m

Saint Thomas Island Cyril E King

sam. 10/4

5:10 pm-8:22 am

2 stops15h 12m

$311

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

dim. 1/18

8:40 am-1:46 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

ven. 1/23

2:59 pm-6:20 pm

Nonstop4h 21m

$330

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

mar. 10/28

7:40 am-1:35 pm

1 stop5h 55m

Saint Thomas Island Cyril E King

sam. 11/1

2:04 pm-7:48 pm

1 stop5h 44m

$331

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

lun. 10/6

5:00 pm-12:27 am

1 stop7h 27m

Santo Domingo Las Americas

mar. 10/21

6:05 am-6:55 pm

1 stop12h 50m

$331

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

mar. 10/21

8:00 am-2:58 pm

1 stop6h 58m

Punta Cana

mer. 10/22

12:35 pm-5:04 pm

Nonstop4h 29m

$339

BostonProvidenciales

BOS - PLS

BOSPLS

Boston Logan Intl

sam. 10/18

6:00 am-12:05 pm

1 stop6h 05m

Providenciales

jeu. 10/23

1:25 pm-11:00 pm

1 stop9h 35m

$348

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, October 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 $223. If you don’t want to visit Caribbean in October, then you should wait until January to fly from Boston, when ticket prices are also cheap, with an average price of $228.

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 $291. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $336. 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 Boston to Caribbean when you can find flight prices for as low as $306. 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 $341.

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 $289 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 $241 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

$136

Fastest flight time

3h 27m

Direct flights

Every day

Airports in Caribbean

4 airports
The best one-way flight to Caribbean from Boston in the past 72 hours is $136. The best round-trip flight deal from Boston to Caribbean found on momondo in the last 72 hours is $282.
The fastest flight from Boston to Caribbean takes 3h 27m
Direct flights go from Boston to Caribbean every day.
There are 4 airports near Caribbean: Nassau Intl (NAS), Providenciales (PLS), Santiago de los Caballeros (STI), San Juan Luis Munoz Marin Intl (SJU)
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 $81Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $99Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
DeltaPriceFrom $142Free CancellationRating
7.9
7,957 reviews
Search Delta flights
JetBluePriceFrom $160Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
ArajetPriceFrom $187Free CancellationRating
7.0
34 reviews
Search Arajet flights
Air CanadaPriceFrom $188Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
Copa AirlinesPriceFrom $192Free CancellationRating
7.6
1,531 reviews
Search Copa Airlines flights
United AirlinesPriceFrom $194Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $288Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
AviancaPriceFrom $356Free CancellationRating
6.7
2,435 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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jeu. 10/16
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Find better results for your trip to Caribbean

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