BOS - SXM

$94 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 2/8. 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, 0 bags

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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

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

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

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

Everything you should know

Cheapest round-trip
$371
Overall average: $741
Delta
Wed 2/25Tue 3/3
BOS - SXM • 1 stop
Cheapest non-stop
$373
Typical prices: $408-$1,457
JetBlue
Sat 12/13Thu 12/18
BOS - SXM • Non-stop
Top airlines
Delta
Cheapest • from $371 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 29% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Simpson Bay!
Flight Deals
Booking Insights
Flight Deals

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

Wed, Feb 25 - Tue, Mar 3
Delta Logo
8:45 pm - 12:15 pmBOS-SXM
14h 30m1 stop
Delta Logo
4:26 pm - 7:24 amSXM-BOS
15h 58m1 stop
$371Delta
Find Deal
Mon, Feb 2 - Thu, Feb 12
United Airlines Logo
7:07 pm - 1:50 pmBOS-SXM
17h 43m2 stops
United Airlines Logo
2:52 pm - 10:36 amSXM-BOS
20h 44m2 stops
$372United Airlines
Find Deal
Sat, Dec 13 - Thu, Dec 18
JetBlue Logo
6:45 am - 11:55 amBOS-SXM
4h 10mnonstop
JetBlue Logo
1:59 pm - 5:34 pmSXM-BOS
4h 35mnonstop
$373JetBlue
Find Deal
Sun, Jan 4 - Sun, Jan 11
American Airlines Logo
6:30 pm - 1:59 pmBOS-SXM
18h 29m1 stop
American Airlines Logo
5:33 pm - 10:29 amSXM-BOS
17h 56m2 stops
$380American Airlines
Find Deal
Tue, Feb 3 - Tue, Feb 17
American Airlines Logo
6:45 am - 4:28 pmBOS-SXM
8h 43m1 stop
American Airlines Logo
1:41 pm - 11:39 amSXM-BOS
22h 58m1 stop
$381American Airlines
Find Deal
Wed, Dec 31 - Wed, Jan 7
JetBlue Logo
7:30 am - 12:44 pmBOS-SXM
4h 14mnonstop
JetBlue Logo
4:25 pm - 11:54 amSXM-BOS
20h 29m1 stop
$382JetBlue
Find Deal
Wed, Feb 4 - Fri, Feb 6
Spirit Airlines Logo
5:45 am - 3:10 pmBOS-SXM
8h 25m1 stop
Spirit Airlines Logo
4:28 pm - 12:40 amSXM-BOS
9h 12m1 stop
$394Spirit Airlines
Find Deal
Thu, Dec 4 - Wed, Dec 10
Multiple Airlines Logo
11:28 am - 2:15 pmBOS-SXM
25h 47m2 stops
Multiple Airlines Logo
3:20 pm - 11:56 pmSXM-BOS
9h 36m1 stop
$395Multiple Airlines
Find Deal
Fri, Jan 2 - Sat, Jan 10
Multiple Airlines Logo
6:00 am - 2:15 pmBOS-SXM
31h 15m2 stops
Multiple Airlines Logo
4:28 pm - 12:40 amSXM-BOS
9h 12m1 stop
$403Multiple Airlines
Find Deal
Tue, Dec 16 - Mon, Dec 22
Spirit Airlines Logo
8:11 pm - 2:15 pmBOS-SXM
17h 04m2 stops
Spirit Airlines Logo
3:20 pm - 11:57 pmSXM-BOS
9h 37m1 stop
$415Spirit Airlines
Find Deal
Booking Insights

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 Saturday, as it's usually the priciest day. When flying back from Simpson Bay, Tuesday is the cheapest day to fly and Saturday 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 $420 (return) on average. On the other hand, the most expensive months are February and December, where the average cost of round-trip tickets is $741 and $741 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $522 on average.

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 8 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 29% 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 $94 for a one-way ticket and $371 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 A321-100/200 is the aircraft model that flies most regularly on the Boston to Simpson Bay flight route.

  • Which airline alliances offer flights from Boston to Simpson Bay?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Boston and Simpson Bay, with SkyTeam being the most commonly used for this 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 $377 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $547 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 $186 or less one-way and $408 or less round-trip.

Prefer to fly direct from Boston to Simpson Bay?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Boston Logan Intl to Simpson Bay Princess Juliana.
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

Monday

JetBlue

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Direct returns

Simpson Bay Princess Juliana to Boston Logan Intl

Monday

JetBlue

JetBlue

Tuesday

JetBlue

JetBlue

Wednesday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Reviews of the 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.
7.9
DeltaOverall score based on 7992 reviews
8.5Crew
8.2Boarding
7.9Comfort
7.9Entertainment
7.3Food
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

The gate agents for spirit at EWR wouldn’t give me my ticket to board when I arrived 50 min from the flight, saying that I wouldn’t make my flight. They tried to reschedule me to arrive at my destination 14 hours after the original flight, which included a 10 hr layover in another city. I rebooked with another airline and it took me a total of 5 min to go through security. Then I see a charge on my card for a $100 change fee that I did not approve. Beware of this horrible place and these horrible people

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

Waited at the airport for over 4 hours to board this flight. Terrible airline

Was supposed to take off 8:00 last night. Got delayed till 8:00 this morning

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

When the flight ticket is expensive and you have to purchase check in luggage and there is no snacks, no entertainment, tight seats stuffed in the back of the plane not such good experience. I would like some to reach out to me . I paid for check luggage when I bought the ticket they made me pay again on the return flight extra $70. Very frustrating.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.