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 25m.

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

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

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 65% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 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 Charlotte (CLT) have the shortest average one-way travel time: 7h 28m.

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

Miami (MIA) was the most common stop: 80% 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 August 2026, there are 6 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.

$143 Cheap Flights from Boston to Simpson Bay in 2026

Discover deals from 900+ travel sites with momondo.

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.

8:50 pm - 1:22 pm

BOS

SXM

16h 32m

2 stops

2:22 pm - 11:26 pm

SXM

BOS

9h 04m

1 stop

$374American Airlines

Sat, Aug 29 - Sat, Sep 5

8:50 pm - 1:22 pm

BOS

SXM

16h 32m

2 stops

4:39 pm - 8:45 am

SXM

BOS

16h 06m

2 stops

$374American Airlines

Sat, Aug 29 - Sat, Sep 5

5:30 am - 1:53 pm

BOS

SXM

8h 23m

1 stop

3:18 pm - 1:17 am

SXM

BOS

9h 59m

1 stop

$379Delta

Mon, Sep 28 - Fri, Oct 2

5:30 am - 1:53 pm

BOS

SXM

8h 23m

1 stop

3:18 pm - 11:31 pm

SXM

BOS

8h 13m

1 stop

$379Delta

Mon, Sep 14 - Fri, Sep 18

9:00 pm - 3:40 pm

BOS

SXM

17h 40m

2 stops

3:20 pm - 8:05 am

SXM

BOS

17h 45m

2 stops

$384Southwest

Sun, Nov 1 - Thu, Nov 5

5:35 am - 2:20 pm

BOS

SXM

7h 45m

1 stop

3:20 pm - 8:10 am

SXM

BOS

17h 50m

2 stops

$384Southwest

Mon, Nov 9 - Fri, Nov 13

6:00 am - 12:33 pm

BOS

SXM

6h 33m

1 stop

1:35 pm - 10:45 pm

SXM

BOS

9h 10m

1 stop

$387United Airlines

Sat, Sep 26 - Sat, Oct 3

6:00 am - 12:33 pm

BOS

SXM

6h 33m

1 stop

1:35 pm - 10:45 pm

SXM

BOS

9h 10m

1 stop

$389United Airlines

Sat, Oct 3 - Sat, Oct 10

5:10 am - 12:37 pm

BOS

SXM

7h 27m

1 stop

1:42 pm - 12:32 am

SXM

BOS

10h 50m

1 stop

$404JetBlue

Mon, Aug 24 - Thu, Aug 27

6:19 am - 2:00 pm

BOS

SXM

7h 41m

1 stop

3:05 pm - 11:39 pm

SXM

BOS

8h 34m

1 stop

$404JetBlue

Sat, Sep 19 - Sat, Sep 26

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American Airlines flights from Boston to Simpson Bay

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

American Airlines

Aug 29

BOS8:50 pmBoston Logan Intl

16h 32m

2 stops

SXM1:22 pmSimpson Bay Princess Juliana

Sep 5

SXM4:39 pmSimpson Bay Princess Juliana

16h 06m

2 stops

BOS8:45 amBoston Logan Intl

$374

American Airlines

Aug 29

BOS8:50 pmBoston Logan Intl

16h 32m

2 stops

SXM1:22 pmSimpson Bay Princess Juliana

Sep 5

SXM4:39 pmSimpson Bay Princess Juliana

17h 05m

2 stops

BOS9:44 amBoston Logan Intl

$379

American Airlines

Aug 29

BOS8:50 pmBoston Logan Intl

16h 32m

2 stops

SXM1:22 pmSimpson Bay Princess Juliana

Sep 5

SXM4:39 pmSimpson Bay Princess Juliana

8h 19m

1 stop

BOS12:58 amBoston Logan Intl

$381

Air Canada flights from Boston to Simpson Bay

Our best Air Canada deals on Boston to Simpson Bay flight tickets

Air Canada

Oct 25

BOS6:35 pmBoston Logan Intl

20h 10m

2 stops

SXM2:45 pmSimpson Bay Princess Juliana

Oct 31

SXM2:40 pmSimpson Bay Princess Juliana

20h 18m

1 stop

BOS10:58 amBoston Logan Intl

$423

Air Canada

Oct 3

BOS6:00 amBoston Logan Intl

11h 00m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Oct 10

SXM6:00 pmSimpson Bay Princess Juliana

17h 55m

1 stop

BOS11:55 amBoston Logan Intl

$424

Air Canada

Sep 19

BOS6:00 amBoston Logan Intl

11h 00m

1 stop

SXM5:00 pmSimpson Bay Princess Juliana

Sep 26

SXM6:00 pmSimpson Bay Princess Juliana

20h 41m

2 stops

BOS2:41 pmBoston Logan Intl

$428

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/29

8:50 pm-1:22 pm

2 stops16h 32m

Simpson Bay Princess Juliana

Sat 9/5

2:22 pm-11:26 pm

1 stop9h 04m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/29

8:50 pm-1:22 pm

2 stops16h 32m

Simpson Bay Princess Juliana

Sat 9/5

4:39 pm-8:45 am

2 stops16h 06m

$374

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 9/28

5:30 am-1:53 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Fri 10/2

3:18 pm-1:17 am

1 stop9h 59m

$379

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 9/14

5:30 am-1:53 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Fri 9/18

3:18 pm-11:31 pm

1 stop8h 13m

$379

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 11/1

9:00 pm-3:40 pm

2 stops17h 40m

Simpson Bay Princess Juliana

Thu 11/5

3:20 pm-8:05 am

2 stops17h 45m

$384

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 11/9

5:35 am-2:20 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Fri 11/13

3:20 pm-8:10 am

2 stops17h 50m

$384

Quickest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/26

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Sat 10/3

1:35 pm-10:45 pm

1 stop9h 10m

$387

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 10/3

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Sat 10/10

1:35 pm-10:45 pm

1 stop9h 10m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 8/24

5:10 am-12:37 pm

1 stop7h 27m

Simpson Bay Princess Juliana

Thu 8/27

1:42 pm-12:32 am

1 stop10h 50m

$404

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/19

6:19 am-2:00 pm

1 stop7h 41m

Simpson Bay Princess Juliana

Sat 9/26

3:05 pm-11:39 pm

1 stop8h 34m

$404

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 typical price of a round-trip flight between Boston and Simpson Bay?

Prices are currently low for flights on this route.

Typical prices usually range from $494 to $659.
The lowest price recently found on this route was $379.

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 $409. If you aren’t able to travel to Simpson Bay during the month of September, then flying in March is also cheap. Prices for this month can be found on momondo for an average of $438.

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

Our data shows that Wednesday 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 $628. 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 from Boston 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 $523 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 $396 on momondo.

What cabin class options are available on Boston to Simpson Bay flights?

There are 4 cabin classes available to choose from on Boston to Simpson Bay 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 6% 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 August 2026, prices for Boston to Simpson Bay flights are approximately 75% 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	$224
Fastest flight time	4h 12m
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 $224. The best round-trip flight deal from Boston to Simpson Bay found on momondo in the last 72 hours is $492.

The fastest flight from Boston to Simpson Bay takes 4h 12m

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

Frequently asked questions about flying from Boston to Simpson Bay

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 12m 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 August 2026, there are 6 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 A318/A319/A320/A321 (60.66% of total bookings). The next most popular plane models are Airbus A321-100/200 (29.51%), Airbus A321neo (6.56%), and Boeing 737 MAX 8 (1.64%).
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 (64% of total bookings). The next most popular airlines are American Airlines (20%), United Airlines (11%), and Delta (3%).

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
Delta	PriceFrom $129	Free Cancellation	Rating 7.8 8,498 reviews	Search Delta flights
Air Canada	PriceFrom $166	Free Cancellation	Rating 7.1 11,415 reviews	Search Air Canada flights
United Airlines	PriceFrom $274	Free Cancellation	Rating 7.4 10,063 reviews	Search United Airlines flights
American Airlines	PriceFrom $282	Free Cancellation	Rating 7.1 11,849 reviews	Search American Airlines flights
JetBlue	PriceFrom $328	Free Cancellation	Rating 7.1 3,029 reviews	Search JetBlue flights

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.

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Cheap flights from Boston to Simpson Bay from $143

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 8/31. 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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American Airlines flights from Boston to Simpson Bay

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

Air Canada flights from Boston to Simpson Bay

Our best Air Canada 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 typical price of a round-trip flight between Boston and 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?

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

What cabin class options are available on Boston to Simpson Bay flights?

Can stopping save me money on Boston to Simpson Bay flights?

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

What is the cheapest airline that flies 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?

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

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

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

When to book flights from Boston to Simpson Bay

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

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

Frequently asked questions about flying 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

Traveling to a place near Simpson Bay?

Why use momondo?

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

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

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