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 10m and 19h 52m, 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 66% 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.

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

Delta, American Airlines, and Southwest 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 June 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.

$124 Cheap Flights from Massachusetts to Simpson Bay in 2026

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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.

6:06 am - 2:15 pm

BOS

SXM

8h 09m

1 stop

3:35 pm - 8:23 am

SXM

BOS

16h 48m

1 stop

$329Delta

Sat, Jul 4 - Sat, Jul 11

6:06 am - 2:15 pm

BOS

SXM

8h 09m

1 stop

3:35 pm - 7:26 am

SXM

BOS

15h 51m

1 stop

$337Delta

Sat, Jul 4 - Sat, Jul 11

6:06 am - 2:15 pm

BOS

SXM

8h 09m

1 stop

3:40 pm - 7:24 am

SXM

BOS

15h 44m

1 stop

$344Delta

Sat, Jun 13 - Sat, Jun 20

6:01 am - 1:51 pm

BDL

SXM

7h 50m

1 stop

2:51 pm - 11:00 pm

SXM

BDL

8h 09m

1 stop

$347American Airlines

Tue, Jul 28 - Tue, Aug 4

6:01 am - 1:51 pm

BDL

SXM

7h 50m

1 stop

4:45 pm - 2:14 pm

SXM

BDL

21h 29m

2 stops

$352American Airlines

Tue, Jul 28 - Tue, Aug 4

6:06 am - 2:15 pm

BOS

SXM

8h 09m

1 stop

3:35 pm - 7:26 am

SXM

BOS

15h 51m

1 stop

$359KLM

Sat, Jul 4 - Sat, Jul 11

5:10 am - 5:00 pm

BOS

SXM

11h 50m

1 stop

6:00 pm - 9:48 am

SXM

BOS

15h 48m

1 stop

$379Air Canada

Sat, Jun 13 - Sat, Jun 20

5:50 am - 5:00 pm

BOS

SXM

11h 10m

2 stops

6:00 pm - 9:48 am

SXM

BOS

15h 48m

1 stop

$382Air Canada

Sat, Jun 13 - Sat, Jun 20

5:45 am - 12:33 pm

BOS

SXM

6h 48m

1 stop

3:50 pm - 11:59 pm

SXM

BOS

8h 09m

1 stop

$385United Airlines

Sat, Jun 13 - Wed, Jun 17

6:00 am - 12:33 pm

BDL

SXM

6h 33m

1 stop

3:50 pm - 10:21 am

SXM

BDL

18h 31m

2 stops

$462United Airlines

Tue, Jun 30 - Tue, Jul 7

Southwest flights from Massachusetts to Simpson Bay

Our best Southwest deals on Massachusetts to Simpson Bay flight tickets

Southwest

Jul 3

BOS10:15 pmBoston Logan Intl

16h 50m

2 stops

SXM3:05 pmSimpson Bay Princess Juliana

Jul 10

SXM2:25 pmSimpson Bay Princess Juliana

17h 40m

2 stops

BOS8:05 amBoston Logan Intl

$416

Southwest

Jun 4

BOS10:15 pmBoston Logan Intl

15h 10m

2 stops

SXM1:25 pmSimpson Bay Princess Juliana

Jun 10

SXM3:00 pmSimpson Bay Princess Juliana

17h 10m

2 stops

BOS8:10 amBoston Logan Intl

$483

Southwest

Jun 6

BOS5:10 amBoston Logan Intl

8h 05m

1 stop

SXM1:15 pmSimpson Bay Princess Juliana

Jun 9

SXM3:00 pmSimpson Bay Princess Juliana

17h 00m

2 stops

BOS8:00 amBoston Logan Intl

$493

JetBlue flights from Massachusetts to Simpson Bay

Our best JetBlue deals on Massachusetts to Simpson Bay flight tickets

JetBlue

Jun 6

BOS7:00 amBoston Logan Intl

4h 07m

SXM11:07 amSimpson Bay Princess Juliana

Jun 13

SXM12:53 pmSimpson Bay Princess Juliana

4h 23m

BOS5:16 pmBoston Logan Intl

$392

JetBlue

Sep 19

BOS6:00 pmBoston Logan Intl

18h 38m

1 stop

SXM12:38 pmSimpson Bay Princess Juliana

Sep 26

SXM1:45 pmSimpson Bay Princess Juliana

10h 40m

1 stop

BOS12:25 amBoston Logan Intl

$437

JetBlue

Jun 6

BOS7:00 amBoston Logan Intl

4h 07m

SXM11:07 amSimpson Bay Princess Juliana

Jun 17

SXM11:17 amSimpson Bay Princess Juliana

20h 29m

1 stop

BOS7:46 amBoston Logan Intl

$490

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 7/4

6:06 am-2:15 pm

1 stop8h 09m

Simpson Bay Princess Juliana

Sat 7/11

3:35 pm-8:23 am

1 stop16h 48m

$329

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 7/4

6:06 am-2:15 pm

1 stop8h 09m

Simpson Bay Princess Juliana

Sat 7/11

3:35 pm-7:26 am

1 stop15h 51m

$337

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 6/13

6:06 am-2:15 pm

1 stop8h 09m

Simpson Bay Princess Juliana

Sat 6/20

3:40 pm-7:24 am

1 stop15h 44m

$344

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Tue 7/28

6:01 am-1:51 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Tue 8/4

2:51 pm-11:00 pm

1 stop8h 09m

$347

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Tue 7/28

6:01 am-1:51 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Tue 8/4

4:45 pm-2:14 pm

2 stops21h 29m

$352

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 7/4

6:06 am-2:15 pm

1 stop8h 09m

Simpson Bay Princess Juliana

Sat 7/11

3:35 pm-7:26 am

1 stop15h 51m

$359

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 6/13

5:10 am-5:00 pm

1 stop11h 50m

Simpson Bay Princess Juliana

Sat 6/20

6:00 pm-9:48 am

1 stop15h 48m

$379

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 6/13

5:50 am-5:00 pm

2 stops11h 10m

Simpson Bay Princess Juliana

Sat 6/20

6:00 pm-9:48 am

1 stop15h 48m

$382

Quickest round-trip

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 6/13

5:45 am-12:33 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Wed 6/17

3:50 pm-11:59 pm

1 stop8h 09m

$385

HartfordSimpson Bay

BDL - SXM

BDLSXM

Hartford Bradley Intl

Tue 6/30

6:00 am-12:33 pm

1 stop6h 33m

Simpson Bay Princess Juliana

Tue 7/7

3:50 pm-10:21 am

2 stops18h 31m

$462

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

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Other information

What is the cheapest month to fly to Simpson Bay?

In general, May 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 $108. If you aren’t able to travel to Simpson Bay during the month of May, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $137.

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 $673. 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 $520 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 $414 on momondo.

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

There are 3 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 10% 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	$222
Fastest flight time	4h 10m
Direct flights	Sun
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Massachusetts in the past 72 hours is $222. The best round-trip flight deal from Massachusetts to Simpson Bay found on momondo in the last 72 hours is $564.

The fastest flight from Massachusetts to Simpson Bay takes 4h 10m

Direct flights go from Massachusetts to Simpson Bay on 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 June 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 A318/A319/A320/A321, making up 44.74% of the total bookings. Other popular models include Airbus A321-100/200 with 35.96%, Airbus A321neo with 13.16%, and Airbus A320-100/200 with 3.51%.

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 8,399 reviews	Search Delta flights
Air Canada	PriceFrom $166	Free Cancellation	Rating 7.1 11,125 reviews	Search Air Canada flights
American Airlines	PriceFrom $282	Free Cancellation	Rating 7.1 11,641 reviews	Search American Airlines flights
United Airlines	PriceFrom $287	Free Cancellation	Rating 7.4 9,772 reviews	Search United Airlines flights
JetBlue	PriceFrom $330	Free Cancellation	Rating 7.1 2,984 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 $124

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 8/28. 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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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

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

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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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