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 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.

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 13m and 19h 50m, respectively.

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

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

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 July 2026, there are 5 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.

$144 Cheap Flights from Massachusetts to Simpson Bay in 2026

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.

7:00 pm - 1:53 pm

BOS

SXM

18h 53m

1 stop

3:18 pm - 12:38 am

SXM

BOS

9h 20m

1 stop

$358KLM

Sat, Aug 29 - Sat, Sep 5

10:00 pm - 2:14 pm

BOS

SXM

16h 14m

1 stop

3:18 pm - 9:39 am

SXM

BOS

18h 21m

1 stop

$367Delta

Fri, Aug 21 - Thu, Aug 27

6:00 am - 12:33 pm

BOS

SXM

6h 33m

1 stop

1:35 pm - 9:33 am

SXM

BOS

19h 58m

2 stops

$382United Airlines

Sat, Sep 26 - Sat, Oct 10

6:00 am - 12:33 pm

BOS

SXM

6h 33m

1 stop

1:35 pm - 9:48 am

SXM

BOS

20h 13m

1 stop

$383United Airlines

Sat, Sep 5 - Sat, Sep 12

5:27 am - 1:42 pm

BOS

SXM

8h 15m

1 stop

2:22 pm - 12:58 am

SXM

BOS

10h 36m

1 stop

$385American Airlines

Mon, Aug 24 - Fri, Aug 28

5:23 pm - 1:42 pm

ORH

SXM

20h 19m

2 stops

4:39 pm - 4:58 pm

SXM

ORH

24h 19m

2 stops

$402American Airlines

Sun, Aug 9 - Sat, Aug 15

5:15 am - 2:20 pm

BDL

SXM

8h 05m

1 stop

3:20 pm - 11:55 pm

SXM

BDL

9h 35m

1 stop

$457Southwest

Wed, Nov 18 - Wed, Nov 25

5:15 am - 2:20 pm

BDL

SXM

8h 05m

1 stop

3:20 pm - 7:50 am

SXM

BDL

17h 30m

2 stops

$462Southwest

Wed, Nov 18 - Wed, Nov 25

6:45 am - 1:54 pm

BDL

SXM

7h 09m

1 stop

1:42 pm - 11:58 pm

SXM

BDL

10h 16m

1 stop

$476JetBlue

Tue, Aug 25 - Thu, Sep 3

6:45 am - 1:54 pm

BDL

SXM

7h 09m

1 stop

1:42 pm - 11:58 pm

SXM

BDL

10h 16m

1 stop

$478JetBlue

Tue, Aug 25 - Thu, Sep 3

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American Airlines flights from Massachusetts to Simpson Bay

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

American Airlines

Aug 24

BOS5:27 amBoston Logan Intl

8h 15m

1 stop

SXM1:42 pmSimpson Bay Princess Juliana

Aug 28

SXM2:22 pmSimpson Bay Princess Juliana

10h 36m

1 stop

BOS12:58 amBoston Logan Intl

$385

American Airlines

Aug 24

BOS6:00 amBoston Logan Intl

9h 39m

2 stops

SXM3:39 pmSimpson Bay Princess Juliana

Aug 28

SXM4:39 pmSimpson Bay Princess Juliana

16h 58m

2 stops

BOS9:37 amBoston Logan Intl

$390

American Airlines

Nov 14

BOS4:52 pmBoston Logan Intl

20h 38m

1 stop

SXM2:30 pmSimpson Bay Princess Juliana

Nov 18

SXM5:33 pmSimpson Bay Princess Juliana

17h 42m

1 stop

BOS10:15 amBoston Logan Intl

$393

United Airlines flights from Massachusetts to Simpson Bay

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

United Airlines

Sep 26

BOS6:00 amBoston Logan Intl

6h 33m

1 stop

SXM12:33 pmSimpson Bay Princess Juliana

Oct 10

SXM1:35 pmSimpson Bay Princess Juliana

19h 58m

2 stops

BOS9:33 amBoston Logan Intl

$382

United Airlines

Sep 5

BOS6:00 amBoston Logan Intl

6h 33m

1 stop

SXM12:33 pmSimpson Bay Princess Juliana

Sep 12

SXM1:35 pmSimpson Bay Princess Juliana

20h 13m

1 stop

BOS9:48 amBoston Logan Intl

$383

United Airlines

Dec 7

BOS6:33 pmBoston Logan Intl

18h 17m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

Dec 11

SXM2:52 pmSimpson Bay Princess Juliana

19h 32m

2 stops

BOS9:24 amBoston Logan Intl

$388

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/29

7:00 pm-1:53 pm

1 stop18h 53m

Simpson Bay Princess Juliana

Sat 9/5

3:18 pm-12:38 am

1 stop9h 20m

$358

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 8/21

10:00 pm-2:14 pm

1 stop16h 14m

Simpson Bay Princess Juliana

Thu 8/27

3:18 pm-9:39 am

1 stop18h 21m

$367

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 10/10

1:35 pm-9:33 am

2 stops19h 58m

$382

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/5

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Sat 9/12

1:35 pm-9:48 am

1 stop20h 13m

$383

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 8/24

5:27 am-1:42 pm

1 stop8h 15m

Simpson Bay Princess Juliana

Fri 8/28

2:22 pm-12:58 am

1 stop10h 36m

$385

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Sun 8/9

5:23 pm-1:42 pm

2 stops20h 19m

Simpson Bay Princess Juliana

Sat 8/15

4:39 pm-4:58 pm

2 stops24h 19m

$402

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 11/18

5:15 am-2:20 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Wed 11/25

3:20 pm-11:55 pm

1 stop9h 35m

$457

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Wed 11/18

5:15 am-2:20 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Wed 11/25

3:20 pm-7:50 am

2 stops17h 30m

$462

Quickest round-trip

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Tue 8/25

6:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Thu 9/3

1:42 pm-11:58 pm

1 stop10h 16m

$476

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Tue 8/25

6:45 am-1:54 pm

1 stop7h 09m

Simpson Bay Princess Juliana

Thu 9/3

1:42 pm-11:58 pm

1 stop10h 16m

$478

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 $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 $441.

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 $632. 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 from Massachusetts 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 $526 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 $387 on momondo.

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

There are 4 cabin classes available to choose from on Massachusetts 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 Massachusetts to Simpson Bay flights?

You could potentially save up to 6% 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	$214
Fastest flight time	4h 13m
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 $214. The best round-trip flight deal from Massachusetts to Simpson Bay found on momondo in the last 72 hours is $492.

The fastest flight from Massachusetts to Simpson Bay takes 4h 13m

Direct flights go from Massachusetts to Simpson Bay every day.

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 July 2026, there are 5 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 A318/A319/A320/A321, making up 60.32% of the total bookings. Other popular models include Airbus A321-100/200 with 30.16%, Airbus A321neo with 6.35%, and Boeing 737 MAX 8 with 1.59%.

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 $129	Free Cancellation	Rating 7.8 8,477 reviews	Search Delta flights
Air Canada	PriceFrom $166	Free Cancellation	Rating 7.1 11,373 reviews	Search Air Canada flights
United Airlines	PriceFrom $274	Free Cancellation	Rating 7.4 10,019 reviews	Search United Airlines flights
American Airlines	PriceFrom $282	Free Cancellation	Rating 7.1 11,835 reviews	Search American Airlines flights
JetBlue	PriceFrom $326	Free Cancellation	Rating 7.1 3,019 reviews	Search JetBlue flights

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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.

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Cheap flights from Massachusetts to Simpson Bay from $144

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 8/16. 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 Massachusetts to Simpson Bay

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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 from Massachusetts to Simpson Bay?

What cabin class options are available on Massachusetts to Simpson Bay 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 long does it take to fly to Simpson Bay?

Cheap Massachusetts to Simpson Bay flight deals and tips

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.

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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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