What is the cheapest airline that flies from Massachusetts to Simpson Bay Princess Juliana?

United Airlines and American Airlines are the most popular carriers operating from Massachusetts 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 Massachusetts according to our data. JetBlue is the first choice among our users, with 67% 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.

How long does it take to fly to Simpson Bay?

If you’re flying from a popular airport in Massachusetts, such as Boston or Worcester, and flying into Simpson Bay, then you can expect flight times to average 4h 05m and 21h 36m, respectively.

How many flights depart from Massachusetts to Simpson Bay on average per week?

The number of flights available between Massachusetts and Simpson Bay is 1 per week as of April 2026. The most frequent departure day is Sat, with 100% of weekly flights leaving on this day.

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

Prices for flights from Massachusetts to Simpson Bay Princess Juliana Airport refresh daily.

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

As of April 2026, there are 6 operators available to choose from for flights from Massachusetts to Simpson Bay Princess Juliana Airport.

How old do you have to be to fly from Massachusetts to Simpson Bay Princess Juliana Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts 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.

$81 Cheap Flights from Massachusetts to Simpson Bay in 2026

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Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Massachusetts to Simpson Bay

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:09 pm - 1:56 pm

BOS

SXM

20h 47m

1 stop

4:35 pm - 12:59 am

SXM

BOS

8h 24m

1 stop

$297American Airlines

Fri, May 1 - Wed, May 6

5:09 pm - 1:56 pm

BOS

SXM

20h 47m

1 stop

4:35 pm - 8:26 am

SXM

BOS

15h 51m

2 stops

$301American Airlines

Fri, May 1 - Wed, May 6

6:00 am - 2:06 pm

BOS

SXM

8h 06m

1 stop

3:35 pm - 7:22 am

SXM

BOS

15h 47m

1 stop

$305Delta

Sat, May 16 - Sat, May 23

7:27 pm - 12:33 pm

BOS

SXM

17h 06m

1 stop

3:50 pm - 11:59 pm

SXM

BOS

8h 09m

1 stop

$310United Airlines

Tue, Jun 2 - Tue, Jun 9

5:45 am - 12:33 pm

BOS

SXM

6h 48m

1 stop

3:50 pm - 9:39 am

SXM

BOS

17h 49m

2 stops

$315United Airlines

Tue, Jun 2 - Tue, Jun 9

5:45 am - 1:30 pm

BOS

SXM

7h 45m

1 stop

2:35 pm - 11:54 pm

SXM

BOS

9h 19m

1 stop

$321Spirit Airlines

Sat, May 16 - Sat, May 30

5:45 am - 12:33 pm

BOS

SXM

6h 48m

1 stop

3:50 pm - 11:01 am

SXM

BOS

19h 11m

2 stops

$322United Airlines

Wed, Apr 29 - Sat, May 2

10:25 am - 1:37 pm

BOS

SXM

27h 12m

3 stops

2:35 pm - 11:54 pm

SXM

BOS

9h 19m

1 stop

$327Spirit Airlines

Sat, May 2 - Sat, May 9

10:45 am - 5:00 pm

BOS

SXM

30h 15m

1 stop

11:30 am - 8:50 pm

SXM

BOS

9h 20m

1 stop

$330Multiple Airlines

Wed, Jun 3 - Sun, Jun 7

5:50 am - 5:00 pm

BOS

SXM

11h 10m

2 stops

6:00 pm - 2:47 pm

SXM

BOS

20h 47m

2 stops

$332Air Canada

Sat, Jun 6 - Sat, Jun 13

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Delta flights from Massachusetts to Simpson Bay

Our best Delta deals on Massachusetts to Simpson Bay flight tickets

Delta

Aug 21

BOS5:45 amBoston Logan Intl

8h 11m

1 stop

SXM1:56 pmSimpson Bay Princess Juliana

Aug 28

SXM3:21 pmSimpson Bay Princess Juliana

9h 45m

1 stop

BOS1:06 amBoston Logan Intl

$305

Delta

Apr 25

BOS8:59 pmBoston Logan Intl

15h 11m

1 stop

SXM12:10 pmSimpson Bay Princess Juliana

Apr 30

SXM3:30 pmSimpson Bay Princess Juliana

15h 59m

1 stop

BOS7:29 amBoston Logan Intl

$313

Delta

Apr 20

BOS8:45 pmBoston Logan Intl

17h 20m

1 stop

SXM2:05 pmSimpson Bay Princess Juliana

Apr 23

SXM3:30 pmSimpson Bay Princess Juliana

15h 59m

1 stop

BOS7:29 amBoston Logan Intl

$332

United Airlines flights from Massachusetts to Simpson Bay

Our best United Airlines deals on Massachusetts to Simpson Bay flight tickets

United Airlines

Jun 2

BOS7:27 pmBoston Logan Intl

17h 06m

1 stop

SXM12:33 pmSimpson Bay Princess Juliana

Jun 9

SXM3:50 pmSimpson Bay Princess Juliana

8h 09m

1 stop

BOS11:59 pmBoston Logan Intl

$310

United Airlines

Jun 2

BOS5:45 amBoston Logan Intl

6h 48m

1 stop

SXM12:33 pmSimpson Bay Princess Juliana

Jun 9

SXM3:50 pmSimpson Bay Princess Juliana

17h 49m

2 stops

BOS9:39 amBoston Logan Intl

$315

United Airlines

Apr 29

BOS5:45 amBoston Logan Intl

6h 48m

1 stop

SXM12:33 pmSimpson Bay Princess Juliana

May 2

SXM3:50 pmSimpson Bay Princess Juliana

19h 11m

2 stops

BOS11:01 amBoston Logan Intl

$322

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 5/1

5:09 pm-1:56 pm

1 stop20h 47m

Simpson Bay Princess Juliana

Wed 5/6

4:35 pm-12:59 am

1 stop8h 24m

$297

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 5/1

5:09 pm-1:56 pm

1 stop20h 47m

Simpson Bay Princess Juliana

Wed 5/6

4:35 pm-8:26 am

2 stops15h 51m

$301

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 5/16

6:00 am-2:06 pm

1 stop8h 06m

Simpson Bay Princess Juliana

Sat 5/23

3:35 pm-7:22 am

1 stop15h 47m

$305

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 6/2

7:27 pm-12:33 pm

1 stop17h 06m

Simpson Bay Princess Juliana

Tue 6/9

3:50 pm-11:59 pm

1 stop8h 09m

$310

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 6/2

5:45 am-12:33 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Tue 6/9

3:50 pm-9:39 am

2 stops17h 49m

$315

Quickest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 5/16

5:45 am-1:30 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Sat 5/30

2:35 pm-11:54 pm

1 stop9h 19m

$321

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 4/29

5:45 am-12:33 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Sat 5/2

3:50 pm-11:01 am

2 stops19h 11m

$322

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 5/2

10:25 am-1:37 pm

3 stops27h 12m

Simpson Bay Princess Juliana

Sat 5/9

2:35 pm-11:54 pm

1 stop9h 19m

$327

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 6/3

10:45 am-5:00 pm

1 stop30h 15m

Simpson Bay Princess Juliana

Sun 6/7

11:30 am-8:50 pm

1 stop9h 20m

$330

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 6/6

5:50 am-5:00 pm

2 stops11h 10m

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-2:47 pm

2 stops20h 47m

$332

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 Massachusetts 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

Other information

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Massachusetts to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $408. 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 $422.

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 Massachusetts to Simpson Bay on a Saturday will generally be more expensive and average around $636. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest Massachusetts to Simpson Bay Princess Juliana flight route?

Fly from Boston Logan Intl to Simpson Bay Princess Juliana for the best Massachusetts - 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 Massachusetts when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $528 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Massachusetts for as low as $412 on momondo.

What cabin class options are available on Massachusetts to Simpson Bay Princess Juliana flights?

There are 3 cabin classes available to choose from on Massachusetts 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 Massachusetts to Simpson Bay flights?

You could potentially save up to 49% on your flight if you consider stops on a Massachusetts to Simpson Bay flight.

Cheap Massachusetts to Simpson Bay flight deals and tips

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

Best Price Found	$566
Fastest flight time	4h 05m
Direct flights	Mon, Wed and Sun
Airports in Simpson Bay	1 airport

The best flight deal from Massachusetts to Simpson Bay found on momondo in the last 72 hours is $566

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

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

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

Search flight deals

Frequently asked questions about flying from Massachusetts to Simpson Bay

When did momondo last update prices for flights from Massachusetts to Simpson Bay Princess Juliana Airport?
Prices for flights from Massachusetts to Simpson Bay Princess Juliana Airport refresh daily.
How many operators does momondo search for flights from Massachusetts to Simpson Bay Princess Juliana Airport?
As of April 2026, there are 6 operators available to choose from for flights from Massachusetts to Simpson Bay Princess Juliana Airport.
How old do you have to be to fly from Massachusetts to Simpson Bay Princess Juliana Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Massachusetts 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 Massachusetts to Simpson Bay?
Based on momondo bookings for flights between Massachusetts and Simpson Bay, the leading plane model is Airbus A321-100/200, making up 47.28% of the total bookings. Other popular models include Airbus A318/A319/A320/A321 with 33.05%, Airbus A321neo with 12.55%, and Airbus A320-100/200 with 5.86%.

Best airlines flying from Massachusetts to Simpson Bay

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

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $136	Free Cancellation	Rating 7.9 8,423 reviews	Search Delta flights
Air Canada	PriceFrom $166	Free Cancellation	Rating 7.1 10,938 reviews	Search Air Canada flights
Spirit Airlines	PriceFrom $205	Free Cancellation	Rating 6.3 8,625 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $297	Free Cancellation	Rating 7.4 9,605 reviews	Search United Airlines flights
American Airlines	PriceFrom $299	Free Cancellation	Rating 7.1 11,615 reviews	Search American Airlines flights
JetBlue	PriceFrom $320	Free Cancellation	Rating 7.2 2,945 reviews	Search JetBlue flights

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

Finding the right flight to Simpson Bay from Massachusetts 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 Massachusetts to Simpson Bay with flexible booking policies on momondo?

Flights from Massachusetts 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 Massachusetts to Simpson Bay?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Simpson Bay from Massachusetts.

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

If you are not ready to book a flight from Massachusetts to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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Cheap flights from Massachusetts to Simpson Bay from $81

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Massachusetts to Simpson Bay departing on 5/17. 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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Delta flights from Massachusetts to Simpson Bay

Our best Delta deals on Massachusetts to Simpson Bay flight tickets

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How to get the cheapest flight ticket from Massachusetts 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 Massachusetts to Simpson Bay Princess Juliana flight route?

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

What cabin class options are available on Massachusetts to Simpson Bay Princess Juliana flights?

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

What is the cheapest airline that flies from Massachusetts to Simpson Bay Princess Juliana?

What airlines fly to Simpson Bay?

How many flights depart from Massachusetts to Simpson Bay on average per week?

How long does it take to fly to Simpson Bay?

Cheap Massachusetts to Simpson Bay flight deals and tips

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

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

Frequently asked questions about flying from Massachusetts to Simpson Bay

Best airlines flying from Massachusetts to Simpson Bay

Compare and see reviews for airlines that fly from Massachusetts 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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