What airlines fly to Simpson Bay?

JetBlue, American Airlines and United Airlines are the top three most popular airlines that fly to Simpson Bay from Boston according to our data. JetBlue is the first choice among our users, with 61% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 7 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Boston to Simpson Bay?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $340.

Which layover airport has the shortest travel time from Boston to Simpson Bay?

Flights connecting via Newark (EWR) have the shortest average one-way travel time: 7h 14m.

What is the cheapest airline that flies from Boston Logan Intl to Simpson Bay Princess Juliana?

Spirit Airlines and JetBlue are the most popular carriers operating from Boston Logan Intl to Simpson Bay Princess Juliana

Which layover airport has the shortest connection time from Boston to Simpson Bay?

Miami (MIA) has the shortest average layover time for this route: 1h 26m.

Which airport is the most popular layover for flights between Boston and Simpson Bay?

Miami (MIA) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

When did momondo last update prices for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

Prices for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport were last updated today.

How many operators does momondo search for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

As of January 2026, there are 7 operators available to choose from for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport.

How old do you have to be to fly from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

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 Simpson Bay Princess Juliana Airport.

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

The necessary travel and health documents for your Simpson Bay Princess Juliana Airport 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.

$65 Cheap Flights from Boston to Simpson Bay in 2026

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Find the cheapest flights from Boston to Simpson Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:23 pm - 2:15 pm

BOS

SXM

19h 52m

1 stop

3:20 pm - 1:13 am

SXM

BOS

10h 53m

2 stops

$316Multiple Airlines

Sat, Feb 7 - Thu, Feb 12

5:45 am - 12:50 pm

BOS

SXM

7h 05m

1 stop

3:50 pm - 12:46 pm

SXM

BOS

20h 56m

2 stops

$318United Airlines

Wed, Mar 25 - Tue, Mar 31

6:53 pm - 1:16 pm

BOS

SXM

18h 23m

2 stops

2:56 pm - 8:26 am

SXM

BOS

17h 30m

1 stop

$319American Airlines

Sat, Apr 25 - Sat, May 2

7:05 am - 2:51 pm

BOS

SXM

7h 46m

1 stop

3:55 pm - 12:56 pm

SXM

BOS

21h 01m

2 stops

$320United Airlines

Fri, Mar 13 - Wed, Mar 18

7:05 am - 2:51 pm

BOS

SXM

7h 46m

1 stop

1:52 pm - 9:41 pm

SXM

BOS

7h 49m

1 stop

$321United Airlines

Fri, Mar 13 - Thu, Mar 19

6:25 pm - 2:15 pm

BOS

SXM

18h 50m

1 stop

4:15 pm - 7:30 am

SXM

BOS

16h 15m

1 stop

$322Delta

Fri, Feb 27 - Thu, Mar 5

5:45 am - 12:50 pm

BOS

SXM

7h 05m

1 stop

3:55 pm - 9:21 am

SXM

BOS

17h 26m

2 stops

$323United Airlines

Thu, Mar 12 - Tue, Mar 17

8:32 pm - 2:15 pm

BOS

SXM

16h 43m

1 stop

4:35 pm - 8:15 pm

SXM

BOS

4h 40mnonstop

$324Multiple Airlines

Sat, Feb 21 - Mon, Mar 2

8:32 pm - 2:15 pm

BOS

SXM

16h 43m

1 stop

3:20 pm - 12:30 am

SXM

BOS

10h 10m

1 stop

$325Multiple Airlines

Sat, Feb 21 - Sat, Feb 28

7:05 am - 2:51 pm

BOS

SXM

7h 46m

1 stop

3:55 pm - 9:21 am

SXM

BOS

17h 26m

2 stops

$326United Airlines

Fri, Mar 13 - Tue, Mar 17

American Airlines flights from Boston to Simpson Bay

Our best American Airlines deals on Boston to Simpson Bay flight tickets

American Airlines

Apr 25

BOS6:53 pmBoston Logan Intl

18h 23m

2 stops

SXM1:16 pmSimpson Bay Princess Juliana

May 2

SXM2:56 pmSimpson Bay Princess Juliana

17h 30m

1 stop

BOS8:26 amBoston Logan Intl

$319

American Airlines

Feb 2

BOS5:00 pmBoston Logan Intl

19h 45m

2 stops

SXM1:45 pmSimpson Bay Princess Juliana

Feb 25

SXM5:28 pmSimpson Bay Princess Juliana

17h 33m

1 stop

BOS10:01 amBoston Logan Intl

$335

American Airlines

Feb 8

BOS8:51 pmBoston Logan Intl

15h 51m

2 stops

SXM1:42 pmSimpson Bay Princess Juliana

Feb 15

SXM5:28 pmSimpson Bay Princess Juliana

8h 31m

1 stop

BOS12:59 amBoston Logan Intl

$336

JetBlue flights from Boston to Simpson Bay

Our best JetBlue deals on Boston to Simpson Bay flight tickets

JetBlue

Feb 25

BOS7:54 amBoston Logan Intl

4h 16m

SXM1:10 pmSimpson Bay Princess Juliana

Mar 3

SXM4:35 pmSimpson Bay Princess Juliana

4h 40m

BOS8:15 pmBoston Logan Intl

$340

JetBlue

Feb 6

BOS8:00 amBoston Logan Intl

4h 15m

SXM1:15 pmSimpson Bay Princess Juliana

Feb 12

SXM4:25 pmSimpson Bay Princess Juliana

4h 40m

BOS8:05 pmBoston Logan Intl

$350

JetBlue

Mar 6

BOS7:54 amBoston Logan Intl

4h 16m

SXM1:10 pmSimpson Bay Princess Juliana

Mar 11

SXM3:35 pmSimpson Bay Princess Juliana

4h 37m

BOS8:12 pmBoston Logan Intl

$353

Fly from

Fly to

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 2/7

5:23 pm-2:15 pm

1 stop19h 52m

Simpson Bay Princess Juliana

Thu 2/12

3:20 pm-1:13 am

2 stops10h 53m

$316

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 3/25

5:45 am-12:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Tue 3/31

3:50 pm-12:46 pm

2 stops20h 56m

$318

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 4/25

6:53 pm-1:16 pm

2 stops18h 23m

Simpson Bay Princess Juliana

Sat 5/2

2:56 pm-8:26 am

1 stop17h 30m

$319

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 3/13

7:05 am-2:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Wed 3/18

3:55 pm-12:56 pm

2 stops21h 01m

$320

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 3/13

7:05 am-2:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Thu 3/19

1:52 pm-9:41 pm

1 stop7h 49m

$321

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 2/27

6:25 pm-2:15 pm

1 stop18h 50m

Simpson Bay Princess Juliana

Thu 3/5

4:15 pm-7:30 am

1 stop16h 15m

$322

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 3/12

5:45 am-12:50 pm

1 stop7h 05m

Simpson Bay Princess Juliana

Tue 3/17

3:55 pm-9:21 am

2 stops17h 26m

$323

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 2/21

8:32 pm-2:15 pm

1 stop16h 43m

Simpson Bay Princess Juliana

Mon 3/2

4:35 pm-8:15 pm

Nonstop4h 40m

$324

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 2/21

8:32 pm-2:15 pm

1 stop16h 43m

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-12:30 am

1 stop10h 10m

$325

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 3/13

7:05 am-2:51 pm

1 stop7h 46m

Simpson Bay Princess Juliana

Tue 3/17

3:55 pm-9:21 am

2 stops17h 26m

$326

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 Boston to Simpson Bay

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

Layovers

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Boston to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $421. If you aren’t able to travel to Simpson Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $487.

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $408. Flights from Boston to Simpson Bay on a Saturday will generally be more expensive and average around $641. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest Boston Logan Intl to Simpson Bay Princess Juliana flight route?

Fly from Boston Logan Intl to Simpson Bay Princess Juliana for the best Boston Logan Intl - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $549 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Boston for as low as $441 on momondo.

What cabin class options are available on Boston Logan Intl to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Boston Logan Intl to Simpson Bay Princess Juliana 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 Simpson Bay flights?

You could potentially save up to 29% on your flight if you consider stops on a Boston to Simpson Bay flight.

How have Boston to Simpson Bay flight prices changed over time?

As of January 2026, prices for Boston to Simpson Bay flights are approximately 134% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Boston to Simpson Bay (BOS to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Simpson Bay

Best Price Found	$149
Fastest flight time	4h 05m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Boston in the past 72 hours is $149. The best round-trip flight deal from Boston to Simpson Bay found on momondo in the last 72 hours is $339.

The fastest flight from Boston to Simpson Bay takes 4h 05m

Direct flights go from Boston to Simpson Bay on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is JetBlue.

There is 1 airport in Simpson Bay. From Boston there are direct flights to Simpson Bay Princess Juliana (SXM).

Search flight deals

How far is Boston Logan Intl to Simpson Bay Princess Juliana by plane?
The straight-line distance from Boston Logan Intl to Simpson Bay Princess Juliana is 1743.0 mi. Typically, this will take 4h 05m by plane in normal conditions.
When did momondo last update prices for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport were last updated today.
How many operators does momondo search for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?
As of January 2026, there are 7 operators available to choose from for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?
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 Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The necessary travel and health documents for your Simpson Bay Princess Juliana Airport 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 Boston to Simpson Bay?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Boston to Simpson Bay is Airbus A321-100/200 (52.30% of total bookings). The next most popular plane models are Airbus A318/A319/A320/A321 (21.41%), Airbus A321neo (14.63%), and Airbus A320-100/200 (10.57%).
What is the most popular airline from Boston to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Boston to Simpson Bay is JetBlue (58% of total bookings). The next most popular airlines are American Airlines (21%), United Airlines (10%), and Delta (5%).

Best airlines flying from Boston to Simpson Bay

Compare and see reviews for airlines that fly from Boston to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $134	Free Cancellation	Rating 5.7 3,056 reviews	Search Frontier flights
Delta	PriceFrom $136	Free Cancellation	Rating 7.9 8,118 reviews	Search Delta flights
Air Canada	PriceFrom $180	Free Cancellation	Rating 7.1 10,660 reviews	Search Air Canada flights
Spirit Airlines	PriceFrom $205	Free Cancellation	Rating 6.3 8,384 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,205 reviews	Search United Airlines flights
JetBlue	PriceFrom $331	Free Cancellation	Rating 7.2 2,890 reviews	Search JetBlue flights
American Airlines	PriceFrom $373	Free Cancellation	Rating 7.2 11,197 reviews	Search American Airlines flights

JetBlue Flights From Boston to Simpson Bay
The lowest priced JetBlue flight from Boston to Simpson Bay from the last 72 hours was $331. Generally, JetBlue has 4 flights on this route every week with an average price of $579. JetBlue is rated 7.2/10 by our users.

Philipsburg

Why use momondo?

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

Finding the right flight to Simpson Bay from Boston 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 Simpson Bay quick and easy, saving you time and money.

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

Flights from Boston to Simpson Bay 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 Simpson Bay?

momondo helps you find the best flight between Boston and Simpson Bay by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Boston to Simpson Bay 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 Simpson Bay trip

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Cheap flights from Boston to Simpson Bay 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 Simpson Bay 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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Filter for what you want

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American Airlines flights from Boston to Simpson Bay

Our best American Airlines deals on Boston to Simpson Bay flight tickets

JetBlue flights from Boston to Simpson Bay

Our best JetBlue deals on Boston to Simpson Bay flight tickets

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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Boston to Simpson Bay

What is the cheapest month to fly to Simpson Bay?

What is the cheapest day to depart on your flight to Simpson Bay?

What is the cheapest Boston Logan Intl to Simpson Bay Princess Juliana flight route?

Fly from Boston Logan Intl to Simpson Bay Princess Juliana for the best Boston Logan Intl - Simpson Bay Princess Juliana flight prices

How far in advance should I book a flight to Simpson Bay?

What cabin class options are available on Boston Logan Intl to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Boston Logan Intl to Simpson Bay Princess Juliana 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 Simpson Bay flights?

You could potentially save up to 29% on your flight if you consider stops on a Boston to Simpson Bay flight.

How have Boston to Simpson Bay flight prices changed over time?

As of January 2026, prices for Boston to Simpson Bay flights are approximately 134% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Boston Logan Intl to Simpson Bay Princess Juliana?

Spirit Airlines and JetBlue are the most popular carriers operating from Boston Logan Intl to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

Which airport is the most popular layover for flights between Boston and Simpson Bay?

Miami (MIA) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Boston to Simpson Bay?

Flights via Charlotte (CLT) offer the lowest average round-trip price of $340.

Which layover airport has the shortest travel time from Boston to Simpson Bay?

Flights connecting via Newark (EWR) have the shortest average one-way travel time: 7h 14m.

Which layover airport has the shortest connection time from Boston to Simpson Bay?

Miami (MIA) has the shortest average layover time for this route: 1h 26m.

When to book flights from Boston to Simpson Bay

Cheap Boston to Simpson Bay (BOS to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Simpson Bay

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

How far is Boston Logan Intl to Simpson Bay Princess Juliana by plane?

When did momondo last update prices for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

How many operators does momondo search for flights from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

How old do you have to be to fly from Boston Logan Intl Airport to Simpson Bay Princess Juliana Airport?

What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

What is the most popular plane model from Boston to Simpson Bay?

What is the most popular airline from Boston to Simpson Bay?

Best airlines flying from Boston to Simpson Bay

Compare and see reviews for airlines that fly from Boston to Simpson Bay with momondo

JetBlue Flights From Boston to Simpson Bay

Traveling to a place near Simpson Bay?

Why use momondo?

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

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

How can momondo help me find flights from Boston to Simpson Bay?

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

An easier way to manage your Simpson Bay 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 St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo