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

Miami (MIA) was the most common stop: 35% of momondo users choosing 1-stop flights on this route connected there.

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

Flights connecting via San Juan (SJU) have the shortest average one-way travel time: 6h 52m.

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

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

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

Flights via San Juan (SJU) offer the lowest average round-trip price of $203.

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 57% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 6 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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 31m.

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 September 2025, 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.

$127 Cheap Flights from Boston to Simpson Bay in 2025

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Boston to Simpson Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

6:10 am - 2:00 pmBOS-SXM

7h 50m1 stop

3:05 pm - 11:59 pmSXM-BOS

8h 54m1 stop

$287Spirit Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 11

6:10 am - 2:00 pmBOS-SXM

7h 50m1 stop

3:05 pm - 11:59 pmSXM-BOS

8h 54m1 stop

$291Spirit Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 11

6:00 am - 12:50 pmBOS-SXM

6h 50m1 stop

2:52 pm - 10:47 pmSXM-BOS

8h 55m1 stop

$335United Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

6:00 am - 12:50 pmBOS-SXM

6h 50m1 stop

2:52 pm - 10:38 amSXM-BOS

20h 46m2 stops

$340United Airlines

Find Deal

Thu, Oct 30 - Mon, Nov 3

8:45 pm - 12:15 pmBOS-SXM

14h 30m1 stop

5:16 pm - 12:59 amSXM-BOS

8h 43m1 stop

$349Delta

Find Deal

Sun, Jan 11 - Sat, Jan 17

5:20 pm - 1:58 pmBOS-SXM

19h 38m2 stops

5:33 pm - 12:59 amSXM-BOS

8h 26m1 stop

$354American Airlines

Find Deal

Sat, Dec 13 - Sat, Dec 20

8:30 pm - 1:53 pmBOS-SXM

17h 23m1 stop

3:45 pm - 7:24 amSXM-BOS

15h 39m1 stop

$363Delta

Find Deal

Mon, Mar 9 - Wed, Mar 11

5:47 am - 1:55 pmBOS-SXM

7h 08m1 stop

5:20 pm - 10:02 amSXM-BOS

17h 42m1 stop

$386American Airlines

Find Deal

Tue, Feb 3 - Tue, Feb 17

10:45 am - 3:57 pmBOS-SXM

4h 12mnonstop

6:00 pm - 9:27 pmSXM-BOS

4h 27mnonstop

$389JetBlue

Find Deal

Sat, Nov 8 - Sat, Nov 15

7:25 am - 12:39 pmBOS-SXM

4h 14mnonstop

6:45 pm - 10:20 pmSXM-BOS

4h 35mnonstop

$399JetBlue

Find Deal

Fri, Jan 2 - Tue, Jan 13

Spirit Airlines flights from Boston to Simpson Bay

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

Spirit Airlines

Oct 4

BOS6:10 amBoston Logan Intl

7h 50m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Oct 11

SXM3:05 pmSimpson Bay Princess Juliana

8h 54m

1 stop

BOS11:59 pmBoston Logan Intl

$287

Find similar

Spirit Airlines

Oct 4

BOS6:10 amBoston Logan Intl

7h 50m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Oct 11

SXM3:05 pmSimpson Bay Princess Juliana

8h 54m

1 stop

BOS11:59 pmBoston Logan Intl

$291

Find similar

Spirit Airlines

Oct 3

BOS6:10 amBoston Logan Intl

7h 50m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Oct 11

SXM3:05 pmSimpson Bay Princess Juliana

8h 54m

1 stop

BOS11:59 pmBoston Logan Intl

$297

Find similar

Delta flights from Boston to Simpson Bay

Our best Delta deals on Boston to Simpson Bay flight tickets

Delta

Jan 11

BOS8:45 pmBoston Logan Intl

14h 30m

1 stop

SXM12:15 pmSimpson Bay Princess Juliana

Jan 17

SXM5:16 pmSimpson Bay Princess Juliana

8h 43m

1 stop

BOS12:59 amBoston Logan Intl

$349

Find similar

Delta

Mar 9

BOS8:30 pmBoston Logan Intl

17h 23m

1 stop

SXM1:53 pmSimpson Bay Princess Juliana

Mar 11

SXM3:45 pmSimpson Bay Princess Juliana

15h 39m

1 stop

BOS7:24 amBoston Logan Intl

$363

Find similar

Delta

Feb 3

BOS5:40 amBoston Logan Intl

8h 16m

1 stop

SXM2:56 pmSimpson Bay Princess Juliana

Feb 10

SXM4:26 pmSimpson Bay Princess Juliana

15h 58m

1 stop

BOS7:24 amBoston Logan Intl

$373

Find similar

Fly from

Fly to

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 10/4

6:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-11:59 pm

1 stop8h 54m

$287

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 10/4

6:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-11:59 pm

1 stop8h 54m

$291

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 10/30

6:00 am-12:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Mon 11/3

2:52 pm-10:47 pm

1 stop8h 55m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 10/30

6:00 am-12:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Mon 11/3

2:52 pm-10:38 am

2 stops20h 46m

$340

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Sat 1/17

5:16 pm-12:59 am

1 stop8h 43m

$349

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 12/13

5:20 pm-1:58 pm

2 stops19h 38m

Simpson Bay Princess Juliana

Sat 12/20

5:33 pm-12:59 am

1 stop8h 26m

$354

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 3/9

8:30 pm-1:53 pm

1 stop17h 23m

Simpson Bay Princess Juliana

Wed 3/11

3:45 pm-7:24 am

1 stop15h 39m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 2/3

5:47 am-1:55 pm

1 stop7h 08m

Simpson Bay Princess Juliana

Tue 2/17

5:20 pm-10:02 am

1 stop17h 42m

$386

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/8

10:45 am-3:57 pm

Nonstop4h 12m

Simpson Bay Princess Juliana

Sat 11/15

6:00 pm-9:27 pm

Nonstop4h 27m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 1/2

7:25 am-12:39 pm

Nonstop4h 14m

Simpson Bay Princess Juliana

Tue 1/13

6:45 pm-10:20 pm

Nonstop4h 35m

$399

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 $460. If you aren’t able to travel to Simpson Bay during the month of September, then flying in October is also cheap. Prices for this month can be found on momondo for an average of $488.

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 Friday will generally be more expensive and average around $1,163. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

According to our data, the cheapest time of day to fly to Simpson Bay is at noon. momondo users have found flights departing from Boston to Simpson Bay at noon for as low as $299. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $679.

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 $602 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 $540 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?

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

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

As of September 2025, prices for Boston to Simpson Bay flights are approximately 56% cheaper 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	$216
Fastest flight time	4h 08m
Direct flights	Every day
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Boston in the past 72 hours is $216. The best round-trip flight deal from Boston to Simpson Bay found on momondo in the last 72 hours is $463.

The fastest flight from Boston to Simpson Bay takes 4h 08m

Direct flights go from Boston to Simpson Bay every day.

There is 1 airport near Simpson Bay: 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 10m 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 September 2025, 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 (51.70% of total bookings). The next most popular plane models are Airbus A321-100/200 (38.07%), Airbus A320-100/200 (5.68%), and Airbus A321neo (2.84%).
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 (56% of total bookings). The next most popular airlines are American Airlines (23%), United Airlines (9%), and Spirit Airlines (6%).

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 $73	Free Cancellation	Rating 5.8 3,177 reviews	Search Frontier flights
Delta	PriceFrom $174	Free Cancellation	Rating 7.9 7,960 reviews	Search Delta flights
United Airlines	PriceFrom $334	Free Cancellation	Rating 7.4 8,937 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $348	Free Cancellation	Rating 6.3 8,023 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $355	Free Cancellation	Rating 7.2 2,913 reviews	Search JetBlue flights
American Airlines	PriceFrom $390	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines 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.

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.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Sat 10/11

Sat 10/18

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Cheap flights from Boston to Simpson Bay from $127

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 12/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Boston to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Spirit Airlines flights from Boston to Simpson Bay

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

Delta flights from Boston to Simpson Bay

Our best Delta deals on Boston to Simpson Bay flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Boston to Simpson Bay that are best for you.

See travel insights to Simpson Bay from

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

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 time of 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?

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

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

As of September 2025, prices for Boston to Simpson Bay flights are approximately 56% cheaper 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?

Frontier, 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: 35% 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 San Juan (SJU) offer the lowest average round-trip price of $203.

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

Flights connecting via San Juan (SJU) have the shortest average one-way travel time: 6h 52m.

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 31m.

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

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