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

Delta, JetBlue, and American Airlines are the most popular carriers operating from Massachusetts to Simpson Bay Princess Juliana

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 08m and 21h 23m, respectively.

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 58% 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.

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 November 2025, there are 7 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.

$74 Cheap Flights from Massachusetts to Simpson Bay in 2025/26

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Find the cheapest flights from Massachusetts to Simpson Bay

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 4:21 pmBDL-SXM

9h 21m1 stop

3:10 pm - 11:57 pmSXM-BDL

8h 47m1 stop

$261JetBlue

Find Deal

Thu, Jan 8 - Wed, Apr 8

6:00 am - 4:51 pmBDL-SXM

9h 51m1 stop

4:25 pm - 11:41 pmSXM-BDL

8h 16m1 stop

$307JetBlue

Find Deal

Sat, Jan 3 - Sat, Jan 10

2:18 pm - 2:22 pmORH-SXM

23h 04m2 stops

2:03 pm - 1:58 pmSXM-ORH

24h 55m2 stops

$310American Airlines

Find Deal

Fri, Jan 30 - Fri, Feb 6

2:18 pm - 2:22 pmORH-SXM

23h 04m2 stops

2:42 pm - 1:58 pmSXM-ORH

24h 16m1 stop

$311American Airlines

Find Deal

Fri, Jan 30 - Fri, Feb 6

6:00 am - 2:31 pmBDL-SXM

7h 31m1 stop

2:03 pm - 11:51 pmSXM-BDL

10h 48m1 stop

$318American Airlines

Find Deal

Thu, Jan 15 - Sat, Jan 24

8:28 am - 2:15 pmBOS-SXM

28h 47m2 stops

3:20 pm - 11:56 pmSXM-BOS

9h 36m1 stop

$363Multiple Airlines

Find Deal

Fri, Dec 5 - Wed, Dec 10

12:08 pm - 2:15 pmBOS-SXM

25h 07m2 stops

3:09 pm - 11:57 pmSXM-BOS

9h 48m1 stop

$367Multiple Airlines

Find Deal

Tue, Dec 30 - Thu, Jan 8

3:43 pm - 2:14 pmBOS-SXM

21h 31m3 stops

3:09 pm - 2:38 pmSXM-BOS

24h 29m2 stops

$368Spirit Airlines

Find Deal

Wed, Jan 28 - Mon, Feb 2

8:00 pm - 2:00 pmBOS-SXM

17h 00m1 stop

3:53 pm - 1:27 amSXM-BOS

10h 34m1 stop

$369Delta

Find Deal

Fri, Dec 5 - Wed, Dec 10

3:43 pm - 2:14 pmBOS-SXM

21h 31m3 stops

3:09 pm - 2:38 pmSXM-BOS

24h 29m2 stops

$371Spirit Airlines

Find Deal

Sat, Jan 24 - Thu, Jan 29

American Airlines flights from Massachusetts to Simpson Bay

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

American Airlines

Jan 30

ORH2:18 pmWorcester

23h 04m

2 stops

SXM2:22 pmSimpson Bay Princess Juliana

Feb 6

SXM2:03 pmSimpson Bay Princess Juliana

24h 55m

2 stops

ORH1:58 pmWorcester

$310

Find similar

American Airlines

Jan 30

ORH2:18 pmWorcester

23h 04m

2 stops

SXM2:22 pmSimpson Bay Princess Juliana

Feb 6

SXM2:42 pmSimpson Bay Princess Juliana

24h 16m

1 stop

ORH1:58 pmWorcester

$311

Find similar

American Airlines

Jan 15

BDL6:00 amHartford Bradley Intl

7h 31m

1 stop

SXM2:31 pmSimpson Bay Princess Juliana

Jan 24

SXM2:03 pmSimpson Bay Princess Juliana

10h 48m

1 stop

BDL11:51 pmHartford Bradley Intl

$318

Find similar

JetBlue flights from Massachusetts to Simpson Bay

Our best JetBlue deals on Massachusetts to Simpson Bay flight tickets

JetBlue

Jan 8

BDL6:00 amHartford Bradley Intl

9h 21m

1 stop

SXM4:21 pmSimpson Bay Princess Juliana

Apr 8

SXM3:10 pmSimpson Bay Princess Juliana

8h 47m

1 stop

BDL11:57 pmHartford Bradley Intl

$261

Find similar

JetBlue

Jan 3

BDL6:00 amHartford Bradley Intl

9h 51m

1 stop

SXM4:51 pmSimpson Bay Princess Juliana

Jan 10

SXM4:25 pmSimpson Bay Princess Juliana

8h 16m

1 stop

BDL11:41 pmHartford Bradley Intl

$307

Find similar

JetBlue

Feb 27

BDL6:00 amHartford Bradley Intl

8h 11m

1 stop

SXM3:11 pmSimpson Bay Princess Juliana

Mar 5

SXM2:25 pmSimpson Bay Princess Juliana

10h 32m

1 stop

BDL11:57 pmHartford Bradley Intl

$362

Find similar

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Thu 1/8

6:00 am-4:21 pm

1 stop9h 21m

Simpson Bay Princess Juliana

Wed 4/8

3:10 pm-11:57 pm

1 stop8h 47m

$261

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Sat 1/3

6:00 am-4:51 pm

1 stop9h 51m

Simpson Bay Princess Juliana

Sat 1/10

4:25 pm-11:41 pm

1 stop8h 16m

$307

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Fri 1/30

2:18 pm-2:22 pm

2 stops23h 04m

Simpson Bay Princess Juliana

Fri 2/6

2:03 pm-1:58 pm

2 stops24h 55m

$310

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Fri 1/30

2:18 pm-2:22 pm

2 stops23h 04m

Simpson Bay Princess Juliana

Fri 2/6

2:42 pm-1:58 pm

1 stop24h 16m

$311

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Thu 1/15

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Sat 1/24

2:03 pm-11:51 pm

1 stop10h 48m

$318

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 12/5

8:28 am-2:15 pm

2 stops28h 47m

Simpson Bay Princess Juliana

Wed 12/10

3:20 pm-11:56 pm

1 stop9h 36m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 12/30

12:08 pm-2:15 pm

2 stops25h 07m

Simpson Bay Princess Juliana

Thu 1/8

3:09 pm-11:57 pm

1 stop9h 48m

$367

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 1/28

3:43 pm-2:14 pm

3 stops21h 31m

Simpson Bay Princess Juliana

Mon 2/2

3:09 pm-2:38 pm

2 stops24h 29m

$368

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 12/5

8:00 pm-2:00 pm

1 stop17h 00m

Simpson Bay Princess Juliana

Wed 12/10

3:53 pm-1:27 am

1 stop10h 34m

$369

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/24

3:43 pm-2:14 pm

3 stops21h 31m

Simpson Bay Princess Juliana

Thu 1/29

3:09 pm-2:38 pm

2 stops24h 29m

$371

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 $420. 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 $508.

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 $759. 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 Massachusetts 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 $663.

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 $585 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 $553 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 30% 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	$186
Fastest flight time	4h 08m
Direct flights	Every day
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Massachusetts in the past 72 hours is $186. The best round-trip flight deal from Massachusetts to Simpson Bay found on momondo in the last 72 hours is $408.

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

Direct flights go from Massachusetts to Simpson Bay every day.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

Search flight deals

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 November 2025, there are 7 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 49.01% of the total bookings. Other popular models include Airbus A318/A319/A320/A321 with 34.87%, Airbus A321neo with 7.89%, and Airbus A320-100/200 with 7.24%.

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
Frontier	PriceFrom $73	Free Cancellation	Rating 5.8 3,106 reviews	Search Frontier flights
Delta	PriceFrom $174	Free Cancellation	Rating 7.9 8,004 reviews	Search Delta flights
Air Canada	PriceFrom $180	Free Cancellation	Rating 7.1 10,462 reviews	Search Air Canada flights
United Airlines	PriceFrom $337	Free Cancellation	Rating 7.4 9,023 reviews	Search United Airlines flights
Spirit Airlines	PriceFrom $338	Free Cancellation	Rating 6.3 8,154 reviews	Search Spirit Airlines flights
JetBlue	PriceFrom $368	Free Cancellation	Rating 7.2 2,903 reviews	Search JetBlue flights
American Airlines	PriceFrom $399	Free Cancellation	Rating 7.2 11,046 reviews	Search American Airlines flights

Philipsburg

Why use momondo?

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.

An easier way to manage your Simpson Bay trip

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Cheap flights from Massachusetts to Simpson Bay from $74

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 12/13. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Massachusetts to Simpson Bay

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American Airlines flights from Massachusetts to Simpson Bay

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

JetBlue flights from Massachusetts to Simpson Bay

Our best JetBlue deals on Massachusetts to Simpson Bay flight tickets

momondo Fare Finder

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

See travel insights to Simpson Bay from

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

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 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?

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 30% on your flight if you consider stops on a Massachusetts to Simpson Bay flight.

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

Delta, JetBlue, and American Airlines are the most popular carriers operating from Massachusetts to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

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 08m and 21h 23m, respectively.

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

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

How many operators does momondo search 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?

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

What is the most popular plane model 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?

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

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

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

I’m not ready to book a flight from Massachusetts 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