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Cheap flights from Boston to Caribbean Islands 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 Islands 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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Find the cheapest flights from Boston to Caribbean Islands

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
Tue, Feb 3 - Tue, Feb 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
Sat, Jan 31 - Sat, Feb 7
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
Sat, Sep 27 - Sat, Oct 4
Delta Logo
6:00 am - 12:24 pmBOS-SDQ
6h 24m1 stop
Delta Logo
6:05 am - 10:27 pmSDQ-BOS
16h 22m1 stop
$322Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
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
Sun, Jan 18 - Fri, Jan 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
Tue, Oct 28 - Sat, Nov 1
United Airlines Logo
6:00 am - 12:50 pmBOS-SXM
6h 50m1 stop
United Airlines Logo
1:52 pm - 9:34 pmSXM-BOS
7h 42m1 stop
$335United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
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
Tue, Oct 21 - Wed, Oct 22
United Airlines Logo
6:00 am - 12:50 pmBOS-SXM
6h 50m1 stop
United Airlines Logo
1:52 pm - 10:34 amSXM-BOS
20h 42m2 stops
$340United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
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
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Sat, Oct 18 - Thu, Oct 23

Frontier flights from Boston to Caribbean Islands

Our best Frontier deals on Boston to Caribbean Islands 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 Islands

Our best Spirit Airlines deals on Boston to Caribbean Islands 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 Islands 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 September 16, 2025.
Use the filters below to find and compare flights from Boston to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 2/3

11:13 am-4:07 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:27 pm-8:34 pm

Nonstop4h 07m

$176

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sat 1/31

11:13 am-4:07 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sat 2/7

5:27 pm-8:34 pm

Nonstop4h 07m

$184

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 9/27

5:47 am-4:00 pm

1 stop10h 13m

Saint Thomas Island Cyril E King

Sat 10/4

5:10 pm-8:22 am

2 stops15h 12m

$311

BostonSanto Domingo

BOS - SDQ

BOSSDQ

Boston Logan Intl

Tue 10/7

6:00 am-12:24 pm

1 stop6h 24m

Santo Domingo Las Americas

Tue 10/14

6:05 am-10:27 pm

1 stop16h 22m

$322

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sun 1/18

8:40 am-1:46 pm

Nonstop4h 06m

Saint Thomas Island Cyril E King

Fri 1/23

2:59 pm-6:20 pm

Nonstop4h 21m

$330

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Tue 10/28

7:40 am-1:35 pm

1 stop5h 55m

Saint Thomas Island Cyril E King

Sat 11/1

2:04 pm-7:48 pm

1 stop5h 44m

$331

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 10/27

6:00 am-12:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 10/31

1:52 pm-9:34 pm

1 stop7h 42m

$335

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

Tue 10/21

8:00 am-2:58 pm

1 stop6h 58m

Punta Cana

Wed 10/22

12:35 pm-5:04 pm

Nonstop4h 29m

$339

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 10/27

6:00 am-12:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 10/31

1:52 pm-10:34 am

2 stops20h 42m

$340

BostonProvidenciales

BOS - PLS

BOSPLS

Boston Logan Intl

Sat 10/18

6:00 am-12:05 pm

1 stop6h 05m

Providenciales

Thu 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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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Boston 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 October is, on average, the cheapest month to fly to Caribbean Islands from Boston, with most prices found around $223. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Boston averaging around $228.

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

The cheapest day to depart from Boston to Caribbean Islands is on a Monday. Travelers who choose to depart for Caribbean Islands on a Monday will often find tickets 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 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 Boston to Caribbean Islands in the morning for as low as $306. 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 in the evening because they tend to be around $341. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Boston Logan Intl to Caribbean Islands flight route?

Fly from Boston Logan Intl to San Juan Luis Munoz Marin Intl for the best Boston Logan Intl - 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 Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands 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 Islands from Boston for as low as $241 on momondo.

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

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

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

Cheap Boston to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 27m

Direct flights

Every day

Airports in Caribbean Islands

4 airports
The fastest flight from Boston to Caribbean Islands takes 3h 27m
Direct flights go from Boston to Caribbean Islands every day.
There are 4 airports near Caribbean Islands: 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 Islands?

    Prices for flights from Boston Logan Intl Airport to Caribbean Islands were last updated today.

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

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

    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 Islands.

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

    The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

Best airlines flying from Boston to Caribbean Islands

Compare and see reviews for airlines that fly from Boston to Caribbean Islands 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 Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Boston to Caribbean Islands. momondo saves you time and could save you money on your trip.

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

Yes. All flights to Caribbean Islands from Boston on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Caribbean Islands from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Boston 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

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