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

BOS - SXM

Find cheap flights from Boston to Simpson Bay from $60

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
Thu 6/6
Thu 6/13

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 43,707,506 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
10:04 am - 3:17 pmBOS-SXM
29h 13m1 stop
4:09 pm - 10:36 amSXM-BOS
18h 27m1 stop
$235Frontier
Find Deal
Fri, May 31 - Mon, Jun 3
10:04 am - 3:17 pmBOS-SXM
29h 13m1 stop
4:14 pm - 8:56 amSXM-BOS
16h 42m1 stop
$236Frontier
Find Deal
Fri, May 31 - Sun, Jun 2
10:04 am - 3:04 pmBOS-SXM
29h 00m1 stop
4:17 pm - 9:04 amSXM-BOS
16h 47m1 stop
$237Frontier
Find Deal
Fri, May 17 - Sun, May 19
6:10 am - 1:48 pmBOS-SXM
7h 38m1 stop
2:44 pm - 6:06 pmSXM-BOS
27h 22m3 stops
$309Spirit Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 12
6:10 am - 1:48 pmBOS-SXM
7h 38m1 stop
2:44 pm - 6:06 pmSXM-BOS
27h 22m3 stops
$311Spirit Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 12
7:18 pm - 1:25 pmBOS-SXM
18h 07m1 stop
2:15 pm - 8:28 amSXM-BOS
18h 13m2 stops
$416American Airlines
Find Deal
Tue, Aug 13 - Tue, Aug 27
8:45 pm - 3:04 pmBOS-SXM
18h 19m2 stops
2:30 pm - 8:29 amSXM-BOS
17h 59m2 stops
$419American Airlines
Find Deal
Sat, Aug 10 - Thu, Aug 15
8:10 am - 12:25 pmBOS-SXM
4h 15mnonstop
1:35 pm - 6:01 pmSXM-BOS
4h 26mnonstop
$445JetBlue
Find Deal
Tue, Jul 16 - Tue, Jul 23
5:15 am - 12:08 pmBOS-SXM
6h 53m1 stop
1:35 pm - 6:01 pmSXM-BOS
4h 26mnonstop
$471JetBlue
Find Deal
Tue, Jul 16 - Tue, Jul 23
7:15 am - 12:35 pmBOS-SXM
29h 20m2 stops
3:55 pm - 6:13 pmSXM-BOS
26h 18m2 stops
$504United Airlines
Find Deal
Fri, May 17 - Sun, May 19

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 $825 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 5 days 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 $60. Frontier proposed a round-trip connection from $235 and Spirit Airlines from $309.

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 $475.

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 21m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 2 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 8:16 am and lands at 12:31 pm.

Good to know

Low season

September

High season

February

Cheapest flight

$60
Best time to beat the crowds with an average 28% 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 $60 for a one-way ticket and $235 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, 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 $586 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 $743 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

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 $235 or less one-way and $490 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

Sunday

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

Sunday

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 10810 reviews
7.9Comfort
8.0Entertainment
8.6Crew
8.2Boarding
7.4Food
Airline reviews

West Jet has a horrible boarding process and the seats have no cushion.

4.0 OkayDouglas, May 2024MSP - YEG
Read more about Delta reviews

West Jet has a horrible boarding process and the seats have no cushion.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

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.

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.

Flight was delayed 2.5 hours - a big deal on an overnight when you plan to sleep.

I feel like they have upgraded the app since I last flew United and I found it to be super helpful. I had stopped flying United unless absolutely necessary and my experience on this trip indicates they have been working hard to improve their services.

Surprisingly easy! I was hesitant to try this, but the cost swayed me. I actually felt like I had less stress than all the taxiing and possible delays that occur with short regional flights where you spend less time in the air than getting to and from the plane..

This flight was delayed multiple times and eventually canceled around 2-3ish. Original take off time was around 10:30am. By 3, there were no other options out of Houston, so stuck in Houston for from 3pm - 11am the next day.

Should have video screens Plane audio was poor and without wired connection hard to understand crew. Should serve more than just cups of water and pretzels on six hour flight. Did not see crew rest of flight. Fix charging sockets to retain charging blocks.

I paid $380 for my one-way ticket from California to Minnesota. The fair did not include online check-in. I received instructions from their app to check in at a kiosk. At the kiosk, the boarding pass would not print until an actual person came to verify that I had a personal item and not a carry-on item, On the plane, the person next to me was drunk and allowed to continue to order alcohol. United is garbage I’d rather fly spirit.

The plane was dirty and the in seat air wasn't blowing as planes usually do.

Generally good but there wasn’t any staff available when my luggage didn’t appear at baggage claim in Fresno. It took about half an hour to locate a staff member to open up the locked room where it was being kept.

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Even though we left CMI late, we mostly made up the time.

Delayed almost 4 hours for a 45 minute flight with no explanation.

Again, multiple delays and I eventually just canceled and drove!

Great crew. Very comfortable business seats with nice bedding. Good food. We were delayed to let late passengers on the flight, but otherwise great experience.

Great crew. We were delayed so that late passengers could get on the flight. Love the bedding in business class. Good food. Great experience.

The CX617 from HK to BKK was delayed more than 1.5 hours.

Horrible - they lied to me about baggage & boarding, even though I specifically spoke to their agents the day before my flight about my issue. When I showed up they did not let me board and stranded me at my airport until I bought a new flight with money I did not have to spend.

I was in business class. There was an excellent headset. But half an hour before arrival they collected them! The rest of the trip I had to use a cheap earphone. There must be a better way to protect the headphones.

All four American Airlines flights I took in last seven days were delayed. Caused me loads of problems, missed meetings, loss of time and money.

American cancelled our flight home. Zero option for hotel, alternative transportation and took 3 hours to find our bags so we could take a 3 hour UBER ride home on our dime. Never flying AA again.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

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 stopFrontier
29h 18mBOS-SXM
$60
6/3Mon
1 stopSpirit Airlines
7h 34mBOS-SXM
$92
6/28Fri
1 stopFrontier
29h 54mBOS-SXM
$108
9/4Wed
1 stop
15h 11mBOS-SXM
$179
9/5Thu
1 stopCopa Airlines
19h 55mBOS-SXM
$196
6/27Thu
1 stopCopa Airlines
26h 37mBOS-SXM
$208
9/4Wed
2 stopsAmerican Airlines
20h 07mBOS-SXM
$214
8/7Wed
2 stopsAmerican Airlines
18h 33mBOS-SXM
$216
6/27Thu
2 stops
21h 29mBOS-SXM
$222
5/18Sat
nonstopJetBlue
4h 21mBOS-SXM
$306

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.
5/11Sat
multi-stopSpirit Airlines
40h 45mBOS-SXM
5/17Fri
multi-stopSpirit Airlines
23h 38mSXM-BOS
$616
5/11Sat
multi-stopSpirit Airlines
40h 45mBOS-SXM
5/17Fri
multi-stopSpirit Airlines
20h 43mSXM-BOS
$663
5/11Sat
multi-stopAmerican Airlines
17h 52mBOS-SXM
5/17Fri
multi-stopAmerican Airlines
11h 48mSXM-BOS
$766
5/10Fri
multi-stopAmerican Airlines
8h 35mBOS-SXM
5/14Tue
multi-stopAmerican Airlines
10h 49mSXM-BOS
$769
5/10Fri
multi-stopAmerican Airlines
18h 18mBOS-SXM
5/14Tue
multi-stopAmerican Airlines
8h 39mSXM-BOS
$772
5/11Sat
nonstopJetBlue
4h 21mBOS-SXM
5/17Fri
multi-stopJetBlue
8h 50mSXM-BOS
$906

Search by stops

Search by airline

Search by price

Boston - Simpson Bay Flights

Departure:

Boston (undefined)United States

Destination:

Simpson Bay (SXM)St. Maarten

Return flight deals:

Simpson Bay - Boston

Cabin classes:

$1,340
$1,333
$445