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BOS - SXM

Find cheap flights from Boston to Simpson Bay from $91

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 5/18. 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
Sat 4/27
Sat 5/4

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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 46,342,885 times on KAYAK, and here is why:

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Cheap flight deals from Boston to Simpson Bay

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
5:05 am - 1:47 pmBOS-SXM
8h 42m1 stop
2:44 pm - 12:57 amSXM-BOS
10h 13m1 stop
$287Spirit Airlines
Find Deal
Wed, May 1 - Sat, May 18
5:05 am - 1:47 pmBOS-SXM
8h 42m1 stop
2:44 pm - 9:50 amSXM-BOS
19h 06m2 stops
$303Spirit Airlines
Find Deal
Wed, May 1 - Wed, May 8
5:05 am - 1:47 pmBOS-SXM
8h 42m1 stop
2:44 pm - 7:21 amSXM-BOS
16h 37m2 stops
Wed, May 1 - Wed, May 8
5:05 am - 1:47 pmBOS-SXM
8h 42m1 stop
2:44 pm - 7:21 amSXM-BOS
16h 37m2 stops
Wed, Apr 24 - Fri, May 3
5:30 am - 1:11 pmBOS-SXM
7h 41m1 stop
2:21 pm - 10:33 pmSXM-BOS
8h 12m1 stop
$350American Airlines
Find Deal
Tue, Apr 30 - Fri, May 3
7:30 am - 3:00 pmBOS-SXM
7h 30m1 stop
2:21 pm - 12:52 amSXM-BOS
10h 31m1 stop
$351American Airlines
Find Deal
Fri, Apr 26 - Fri, May 3
5:45 am - 1:35 pmBOS-SXM
7h 50m1 stop
2:22 pm - 1:03 amSXM-BOS
10h 41m1 stop
$353Delta
Find Deal
Mon, Apr 8 - Wed, Apr 10
9:35 pm - 1:55 pmBOS-SXM
16h 20m1 stop
2:22 pm - 9:45 amSXM-BOS
19h 23m1 stop
$358Delta
Find Deal
Sun, Apr 21 - Tue, Apr 23
8:10 am - 12:25 pmBOS-SXM
4h 15mnonstop
1:35 pm - 6:01 pmSXM-BOS
4h 26mnonstop
$445JetBlue
Find Deal
Thu, Jul 11 - Tue, Jul 16
7:40 am - 2:11 pmBOS-SXM
6h 31m1 stop
1:35 pm - 6:01 pmSXM-BOS
4h 26mnonstop
$480JetBlue
Find Deal
Sun, Jun 9 - Thu, Jun 13

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 $504 on average. On the other hand, the most expensive months are April and July, where the average cost of tickets is $894 and $873 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 2 days before departure. For the absolute cheapest price, our data suggests you should book 71 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 Spirit Airlines for $91. Spirit Airlines proposed a round-trip connection from $287 and American Airlines from $350.

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 $484.

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 08m. The most common departure time is 10:00 am and most flights take off in the morning. Each week, there are 1 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 4h 12m 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 6:19 am and will be landing in Simpson Bay at 10:40 am.

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 10:52 am and lands at 3:00 pm.

Good to know

Low season

September

High season

February

Cheapest flight

$91
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 5% 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 $91 for a one-way ticket and $287 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?

    Only JetBlue offers 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 Saturday, and Sunday.

  • 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 $604 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 $782 and an overall rating of 7.7.

  • 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

Top tips for finding a cheap flight from BOS to Simpson Bay

  • Looking for a cheap flight? 25% of our users found flights on this route for $364 or less one-way and $605 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

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Nonstop returns

Simpson Bay Princess Juliana to Boston Logan Intl

Saturday

JetBlue, Qatar Airways

JetBlue, Qatar Airways

Sunday

JetBlue, Qatar Airways

JetBlue, Qatar Airways

See more direct flights
See more direct flights

Top 5 airlines serving from Boston to Simpson Bay

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 KAYAK reviews.
8.0
DeltaOverall score based on 11402 reviews
75food
80entertainment
79comfort
82boarding
86crew
81overall
Airline reviews

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

Read more about Delta

Carly the flight attendant was extremely helpful and very accommodating to passengers on the flight from what I noticed. Couldn't be more satisfied with the service and assistance from Delta's flight attendant, Thanks again Carly!!

I didn’t not like that I could not select my seat and ended up with the worse seat.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Inflight entertainment stopped working as we taxi to runway and never worked again until landing and taxi to gate. Grrrr

Had to run to make it only to have the flight delayed to wait for all the late connectors Second drink service skipped up

Boarding was a sh!t show. JFK BOARDING was awful. The agent called three sections at a time Clogging the area then yelling at people to not block the walk way. How are you going to call delta one , premium select and comfort plus at once and the yell at highest paying passengers. Need to do a lot better and the flight attendants in the galley need to understand that their voices travel. They were talking about others and everyone in the cabin heard them

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

Please see my lengthy description on MSP to Atlanta survey. Tailbone is killing me from old hard seats. Seat would not recline and were not near exit row. Entertainment did not work properly and couldn’t use. No audio and touch screen failed. 3 plus hours of discomfort in narrower seats than previous flight not in comfort plus. Very dissatisfied and deserve comfort plus charges refunds, at the very least, for both my wife and I. The plane needs to be retired. Please feel free to contact me directly for further details.

MSP to Atlanta was much better than Atlanta to St. Kitts. Paid $180 each for myself and wife for Delta comfort from Atlanta to St. Kitts. Seats were more narrow and obviously old and worn out. Tailbone is killing me. Seat would not recline. Seats behind reclined and we were not an exit row or in front of an exit row. Entertainment did not work in that the movie jumped forward and back and there was no audio. The plug in the arm rest was loose. Flight attendant tried “resetting” the video for my seat but no good. She never checked back. Someone else near me had the same issue. Touch screen was unresponsive. No where near as comfortable as MSP to Atlanta flight. 3 plus hrs. flight time without the basic amenities and not even remotely close to comfortable but paid for Comfort plus. I will be very disappointed if I have the same on my return “Comfort Plus” flight St. Kitts to Atlanta. At the very least my wife and I should be refunded for round trip “Comfort Plus” charges. Please feel free to contact me directly for more details.

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.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

ticketing issues caused many customers to have to go back to check in after waiting in security, then go through security line again.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

Overall it was good. The flight was bumpy at times, but the pilot made us aware every time. As a result, no snacks/drinks were made available. Seats were tight but that’s okay as I had a window seat.

Plane didn’t even make it off the ground. We all had to get off and walk to a different terminal (lots of confusion) to get on a different plane. Landed fairly late, connections missed.

the head jack on my seat didn't work and the power outlet didn't work for my seat

All good except paid for wifi that did not work

Beverage and food services are excellent. We enjoy paying the extra for economy plus for the 3 inches more leg room to be exact.

Left 2 hours later for delayed I had to take care a kid with special need since people don’t want to move to accommodate the rest of the family. . It wasn’t bad but that made me upset that people can be that selfish.

The crew were really great, but the 4 hour delay in small chunks was the worst.

They did get us booked on a later flight, but it made us miss our connecting flight. So, we had to stay and another state overnight with no luggage or clothes. Because they kept our luggage at airport for next flight on the next day.

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Plane was good but was delayed. probably not AA fault but caused a 1 hour delay. Seating was cramped.

Flight was good and arrived a little early. Very good.

Gossipy flight attendants talked the whole flight about bar hopping and dating.

Turbulence was bad and flight attendants gossiped about going to the bar and dating. Could have better awareness.

When we exited the plane our wheelchair wasn’t there. The Pilot and co pilot were so nice and helped us locate it. Great service.

Didn't like the 6 hour delay as it caused me to miss all of my connections. Still, I did get home safely 14 hours late but exhausted.

New ridiculous policy by american destroyed my allegiance to american. As a million miler with american, I expected it would be easy to get on an earlier flight when I got to airport earlier than expected, and save a five hour layover. WRONG. The online app would not let me switch flights, So I called, and was promised a call back in 90 minutes. HAH! The customer service desk at DCA said “we no longer have access to changing a flight on our screens. If the app couldn’t do it, I should send a letter to American, but there’s nothing else possible!”

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Same basket of unhealthy prepackaged snacks (junk food) which was depleted by the time it got to my row!!

3 hour delay was brutal though not Spirit Airlines fault. the control tower would not let us take off because of weather

Beware of all the extras. Nickel and dimed. Everything was extra. It turns a $90 fare in to a $400 fair quite easily.

I flew from Las Vegas to Reno Nevada. Airfare was 60 $ round trip. I needed to bring my skis and boots.that was going to be $111 to bring them. Upon arrival they informed me that anyone who has skis more than 62 inches long is charged an oversize fee of $150 each way. Almost everyone over 5 foot five has skis over 62 inches long. So I paid $60 for the flight and $411 to bring my skis with me! WTF

Didn’t make the connecting flight due to a delay on our first flight.

I like the price. I did not like the seats: very little space and not reclining.

Flights are great except for the ticketing service on the terminal.. Too little employees taking care for lots of flights.

The seats were very uncomfortable. The crew was very polite and helpful.

The airplane was extremely hot the air conditioner wasn’t working I

The text told me it was changed to Terminal E and Gate D5. But with no one on site to ask questions there was confusion on where to go as all the gates were E's. Then we took the skyline to the D area. We left to get something to eat. No announcement was made but my daughter happened to asked and they told her our gate was moved to D12. I will not fly Spirit again.

Seats horrible. No way of getting comfortable . But flight ran smoothly

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.
5/18Sat
1 stopSpirit Airlines
7h 34mBOS-SXM
$91
4/26Fri
2 stopsSpirit Airlines
19h 46mBOS-SXM
$121
5/4Sat
2 stopsAmerican Airlines
18h 14mBOS-SXM
$135
5/4Sat
1 stopDelta
17h 47mBOS-SXM
$136
4/26Fri
1 stopAmerican Airlines
17h 58mBOS-SXM
$137
4/16Tue
2 stopsAmerican Airlines
16h 59mBOS-SXM
$142
5/18Sat
2 stops
16h 40mBOS-SXM
$144
5/18Sat
nonstopJetBlue
4h 21mBOS-SXM
$335
5/4Sat
nonstopJetBlue
4h 21mBOS-SXM
$385
9/22Sun
3 stopsUnited Airlines
40h 47mBOS-SXM
$1,535

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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.
3/31Sun
multi-stopSpirit Airlines
7h 34mBOS-SXM
4/7Sun
multi-stopSpirit Airlines
28h 59mSXM-BOS
$548
3/31Sun
multi-stopSpirit Airlines
20h 04mBOS-SXM
4/7Sun
multi-stopSpirit Airlines
28h 59mSXM-BOS
$640
3/31Sun
multi-stopUnited Airlines
30h 50mBOS-SXM
4/7Sun
multi-stopUnited Airlines
18h 54mSXM-BOS
$822

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Boston - Simpson Bay Flights

Departure:

Boston (BOS)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Boston

Cabin classes:

$1,340
$1,333
$505