BOS - SXM

$138 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 9/6. 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
1 adult, Economy

KAYAK searches 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.
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Cheap Flights 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 for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Boston to Simpson Bay

Sat, Aug 9 - Wed, Aug 13
United Airlines Logo
5:30 am - 12:29 pmBOS-SXM
6h 59m1 stop
United Airlines Logo
3:55 pm - 11:59 pmSXM-BOS
8h 04m1 stop
$322United Airlines
Find Deal
Sat, Aug 9 - Wed, Aug 13
United Airlines Logo
5:30 am - 12:29 pmBOS-SXM
6h 59m1 stop
United Airlines Logo
3:55 pm - 10:57 amSXM-BOS
19h 02m2 stops
$327United Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
5:35 am - 1:56 pmBOS-SXM
8h 21m1 stop
Delta Logo
3:21 pm - 1:20 amSXM-BOS
9h 59m1 stop
$335Delta
Find Deal
Sat, Aug 16 - Sat, Aug 23
Delta Logo
5:35 am - 1:56 pmBOS-SXM
8h 21m1 stop
Delta Logo
3:21 pm - 1:20 amSXM-BOS
9h 59m1 stop
$345Delta
Find Deal
Sat, Jul 12 - Wed, Jul 16
Spirit Airlines Logo
6:10 am - 2:00 pmBOS-SXM
7h 50m1 stop
Spirit Airlines Logo
3:05 pm - 11:48 pmSXM-BOS
8h 43m1 stop
$377Spirit Airlines
Find Deal
Fri, Aug 15 - Mon, Aug 18
Spirit Airlines Logo
6:10 am - 2:24 pmBOS-SXM
8h 14m1 stop
Spirit Airlines Logo
3:27 pm - 12:39 amSXM-BOS
9h 12m1 stop
$381Spirit Airlines
Find Deal
Sat, Aug 23 - Sat, Aug 30
JetBlue Logo
7:50 am - 12:00 pmBOS-SXM
4h 10mnonstop
JetBlue Logo
1:25 pm - 5:51 pmSXM-BOS
4h 26mnonstop
$409JetBlue
Find Deal
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
6:43 pm - 3:09 pmBOS-SXM
20h 26m2 stops
American Airlines Logo
4:30 pm - 8:42 amSXM-BOS
16h 12m2 stops
$428American Airlines
Find Deal
Tue, Aug 19 - Sun, Aug 24
American Airlines Logo
8:30 pm - 3:09 pmBOS-SXM
18h 39m2 stops
American Airlines Logo
4:30 pm - 12:48 amSXM-BOS
8h 18m1 stop
$433American Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
JetBlue Logo
7:50 am - 12:00 pmBOS-SXM
4h 10mnonstop
JetBlue Logo
1:25 pm - 5:51 pmSXM-BOS
4h 26mnonstop
$439JetBlue
Find Deal
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KAYAK's insights & trends for Boston to Simpson Bay flights

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 round-trip flights from Boston to Simpson Bay clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Boston to Simpson Bay, look for departures on Wednesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Simpson Bay, Tuesday is the cheapest day to fly and Thursday is the most expensive.

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 round-trip 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 $421 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $897 and $779 respectively.

Can I save money by flying with a layover from Boston to Simpson Bay?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $1,001, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip 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 week.

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 4 weeks before departure.

Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$138
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 26% 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 $138 for a one-way ticket and $322 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 Saturday.

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

    The two airlines most popular with KAYAK users for flights from Boston to Simpson Bay are Delta and United Airlines. With an average price for the route of $444 and an overall rating of 8.0, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $552 and an overall rating of 7.4.

  • 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.

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 $326 or less one-way and $468 or less round-trip.

Prefer to fly direct from Boston to Simpson Bay?

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

Direct departures

Boston Logan Intl to Simpson Bay Princess Juliana

Saturday

JetBlue

JetBlue

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Boston Logan Intl

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 7950 reviews
8.2Boarding
7.3Food
8.5Crew
7.9Comfort
7.9Entertainment
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Everything you need to know for your flight from Boston to Simpson Bay

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