Find flights
Deals
Insights
When to book
FAQs & Tips
Direct Flights
Airlines

BOS - SXM

$103 Find cheap flights from Boston to Simpson Bay

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Simpson Bay departing on 6/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Tue 7/9
Tue 7/16

Search hundreds of travel sites at once for deals on flights to Simpson Bay

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Simpson Bay.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Simpson Bay.
In the last 7 days travelers have searched 42,898,604 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Boston to Simpson Bay (BOS-SXM)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Simpson Bay that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
9:16 am - 3:10 pmBOS-SXM
29h 54m1 stop
6:25 pm - 10:25 amSXM-BOS
16h 00m1 stop
$243Frontier
Find Deal
Fri, Jun 21 - Mon, Jun 24
9:16 am - 3:10 pmBOS-SXM
29h 54m1 stop
6:25 pm - 10:25 amSXM-BOS
16h 00m1 stop
$259Frontier
Find Deal
Fri, Jun 21 - Mon, Jun 24
12:09 pm - 2:09 pmBOS-SXM
26h 00m1 stop
3:07 pm - 12:39 amSXM-BOS
9h 32m1 stop
$358Spirit Airlines
Find Deal
Tue, Sep 17 - Sat, Sep 21
5:39 pm - 2:05 pmBOS-SXM
20h 26m1 stop
3:05 pm - 11:33 pmSXM-BOS
8h 28m1 stop
$365Spirit Airlines
Find Deal
Tue, Jul 9 - Wed, Jul 17
5:57 am - 1:25 pmBOS-SXM
7h 28m1 stop
2:35 pm - 11:30 pmSXM-BOS
8h 55m1 stop
$415American Airlines
Find Deal
Sun, Sep 1 - Fri, Sep 6
8:31 pm - 1:19 pmBOS-SXM
16h 48m2 stops
2:35 pm - 11:30 pmSXM-BOS
8h 55m1 stop
$419American Airlines
Find Deal
Sun, Sep 1 - Fri, Sep 6
8:16 am - 12:31 pmBOS-SXM
4h 15mnonstop
1:45 pm - 6:10 pmSXM-BOS
4h 25mnonstop
$445JetBlue
Find Deal
Thu, Aug 1 - Tue, Aug 6
6:15 am - 1:19 pmBOS-SXM
7h 04m1 stop
2:30 pm - 6:53 pmSXM-BOS
4h 23mnonstop
$471JetBlue
Find Deal
Sat, Aug 17 - Sat, Aug 24
7:35 pm - 1:38 pmBOS-SXM
18h 03m1 stop
4:55 pm - 11:54 pmSXM-BOS
7h 59m1 stop
$495United Airlines
Find Deal
Sat, Nov 2 - Tue, Nov 12
6:30 pm - 1:38 pmBOS-SXM
19h 08m2 stops
4:55 pm - 10:29 amSXM-BOS
18h 34m2 stops
$499United Airlines
Find Deal
Sat, Nov 2 - Tue, Nov 12

Flights from Boston to Simpson Bay - Travel Insights & Trends

Get data-powered insights and trends into flights from Boston to Simpson Bay to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Boston to Simpson Bay?

The average price of all flights from Boston to Simpson Bay clicked on KAYAK for each day over the last 12 months.
When flying from Boston to Simpson Bay, you should consider leaving on a Tuesday and avoid Saturdays if you are looking for the best rates. For your return to Boston, you’ll find the best rates on Mondays and the most expensive ones on Saturdays.

What is the cheapest month to fly from Boston to Simpson Bay?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Boston to Simpson Bay is September, where tickets cost $503 on average. On the other hand, the most expensive months are April and March, where the average cost of tickets is $849 and $817 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Boston to Simpson Bay, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Boston to Simpson Bay, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 days before departure.

Which airlines provide the cheapest flights from Boston to Simpson Bay?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Boston to Simpson Bay found on KAYAK was with Frontier for $103. Frontier proposed a round-trip connection from $243 and Spirit Airlines from $358.

Which airlines fly non-stop between Boston and Simpson Bay?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Boston to Simpson Bay.
There is just one airline that flies from Boston to Simpson Bay direct and that is JetBlue. The best one-way deal found from JetBlue for the route is $471.

How many flights are there between Boston and Simpson Bay per day?

There is a maximum of 1 nonstop flight a day that takes off from Boston and lands in Simpson Bay, with an average flight time of 4h 12m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 3 flights.

Which cabin class options are there for flights between Boston and Simpson Bay?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 2 cabin class options for the route. These are Business and Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Boston to Simpson Bay take?

A direct flight to Simpson Bay will take on average 3h 59m to travel the 1,742 miles flying distance from Boston.

What’s the earliest departure time from Boston to Simpson Bay?

Early birds can take the earliest flight from Boston at 7:48 am and will be landing in Simpson Bay at 12:00 pm.

What’s the latest departure time from Boston to Simpson Bay?

If you prefer to fly at night, the latest flight from Boston to Simpson Bay jets off at 8:55 am and lands at 1:07 pm.

Good to know

Low season

September

High season

February

Cheapest flight

$103
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Boston to Simpson Bay

When to book flights from Boston to Simpson Bay

Are your dates flexible? Find out the best times to travel from Boston to Simpson Bay based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Boston to Simpson Bay

  • What is the cheapest flight from Boston to Simpson Bay?

    In the last 3 days, the lowest price for a flight from Boston to Simpson Bay was $103 for a one-way ticket and $243 for a round-trip.

  • Do I need a passport to fly between Boston and Simpson Bay?

    Yes

  • Which airports will I be using when flying from Boston to Simpson Bay?

    When flying out of Boston you will be using Boston Logan Intl. You will be landing at Simpson Bay, also known as Simpson Bay Princess Juliana.

  • Which airlines offer Wi-Fi service onboard planes from Boston to Simpson Bay?

    JetBlue, and Delta offer inflight Wi-Fi service on the Boston to Simpson Bay flight route.

  • Which aircraft models fly most regularly from Boston to Simpson Bay?

    The Airbus A318/A319/A320/A321 is the aircraft model that flies most regularly on the Boston to Simpson Bay flight route.

  • On which days can I fly direct from Boston to Simpson Bay?

    You can catch a nonstop flight from Boston to Simpson Bay on on Tuesday, Thursday, and Saturday.

  • Which is the best airline for flights from Boston to Simpson Bay, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Boston to Simpson Bay are Delta and JetBlue. With an average price for the route of $581 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $725 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Boston to Simpson Bay?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Simpson Bay.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Simpson Bay?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Simpson Bay from Boston is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Simpson Bay?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Simpson Bay with an airline and back to Boston with another airline. Booking your flights between Boston and SXM can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Simpson Bay?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Simpson Bay from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Boston to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $235 or less one-way and $505 or less round-trip.

Prefer to fly non-stop from Boston to Simpson Bay?

Find which airlines fly direct from Logan Intl to Princess Juliana, which days they fly and book direct flights.

Nonstop departures

Boston Logan Intl to Simpson Bay Princess Juliana

Tuesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Boston Logan Intl

Tuesday

JetBlue, Qatar Airways

JetBlue, Qatar Airways

Thursday

JetBlue, Qatar Airways

JetBlue, Qatar Airways

Saturday

JetBlue, Qatar Airways

JetBlue, Qatar Airways

See more direct flights
See more direct flights

Top 5 airlines serving from Boston to Simpson Bay

 
See real verified KAYAK customer reviews for airlines flying from Boston to Simpson Bay. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Simpson Bay? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10295 reviews
8.2Boarding
7.9Comfort
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Overall fine but both ways for this trip was delayed.

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

Why does it have to be painful to fly long distances?

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

Original plane sidelined. Had to wait an hour for replacement.

Crew was very cooperative and professional. Passenger's first checked in bag should be free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

Horrible, the flights kept delaying, so it is obvious that we won't be able to make it to the next connection. No easier/real agent on site to help you figure this out. UA agent on other counters refuse to assist you and direct us to use the QR code/call customer service. So inefficient and poor. While technology seems convenient, but it's not the best interest/experience for customers need help while there is active issue need assistance.

Food is very bad and entertint not too many options ... flight attendet service is not good

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

My window shade didn’t work. So I missed coming into my city. ☹️

Flight was delayed in the gate by 5 hours and ultimately cancelled- rebooking service by United agents was terrible

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Information when booking said the flight would be with American Airlines but the flight was actualy with British Airways. Check in from Orlando was nice and quick. I agreed to put my cabin case in the checked luggage as it was a full flight. Case came back damaged (unable to put the handle down) so will have to dispose of it. Seats were quite cramped with very little leg room, even for economy. This was the experience of both the outgoing and return flight. Cabin crew were ok and flight time was punctual.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Missed this flight due to the first AA flight delay

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Not enough help at airport during boarding process. Flight was delayed. Overall WORST flying experience I’ve ever had. Will NEVER FLT SPIRIT AGAIN

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

Could have TV/Movie and some water ou soda free

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

Book cheap flights from Boston to Simpson Bay

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Boston to Simpson Bay found on KAYAK in the last 72 hours.
6/28Fri
1 stopFrontier
29h 54mBOS-SXM
$103
8/1Thu
1 stopFrontier
28h 57mBOS-SXM
$138
7/9Tue
1 stopSpirit Airlines
20h 26mBOS-SXM
$144
7/9Tue
2 stopsSpirit Airlines
18h 05mBOS-SXM
$154
6/27Thu
2 stops
29h 08mBOS-SXM
$162
7/2Tue
nonstopJetBlue
4h 15mBOS-SXM
$206
7/6Sat
2 stopsAmerican Airlines
16h 55mBOS-SXM
$216
7/7Sun
1 stopUnited Airlines
7h 05mBOS-SXM
$232
7/8Mon
1 stopAmerican Airlines
7h 55mBOS-SXM
$256
6/27Thu
nonstopJetBlue
4h 15mBOS-SXM
$266

Search by stops

Search by airline

Search by price

Last minute flights from Boston to Simpson Bay

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Boston to Simpson Bay that are departing in the next 10 days.
6/13Thu
multi-stop
29h 08mBOS-SXM
6/15Sat
multi-stop
9h 55mSXM-BOS
$603
6/13Thu
multi-stopSpirit Airlines
21h 06mBOS-SXM
6/15Sat
multi-stopSpirit Airlines
9h 55mSXM-BOS
$614
6/13Thu
multi-stopSpirit Airlines
21h 32mBOS-SXM
6/15Sat
multi-stopSpirit Airlines
22h 19mSXM-BOS
$655
6/13Thu
multi-stopSpirit Airlines
27h 07mBOS-SXM
6/15Sat
multi-stopSpirit Airlines
20h 33mSXM-BOS
$685
6/13Thu
multi-stopSpirit Airlines
20h 13mBOS-SXM
6/15Sat
multi-stopSpirit Airlines
28h 26mSXM-BOS
$719
6/13Thu
nonstopJetBlue
4h 15mBOS-SXM
6/15Sat
nonstopJetBlue
4h 23mSXM-BOS
$866
6/13Thu
nonstopJetBlue
4h 15mBOS-SXM
6/15Sat
multi-stopJetBlue
9h 23mSXM-BOS
$876

Search by stops

Search by airline

Search by price

Boston - Simpson Bay Flights

Departure:

Boston (BOS)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Boston

Cabin classes:

$1,140
$805
$445