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Simpson Bay

$138+ Cheap flights from Boston (BOS) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SXM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Boston Logan Intl to Simpson Bay Princess Juliana are usually found in September or August, booked 13 days in advance, depart on a Wednesday or Monday and return on a Monday

Cheap flight deals from Boston to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated June 12, 2025.

Round-trip from

$322
(United Airlines)

One-way from

$138
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$554

Good round-trip deal

$468 or less

Good one-way deal

$326 or less
From Boston Logan Intl to Simpson Bay Princess Juliana
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One-way flight from Boston Logan Intl to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 12% potential increase in price ($88 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Simpson Bay Princess Juliana.
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Price to beat on a one-way flight from Boston Logan Intl to Simpson Bay Princess Juliana.
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Find flight deals from Boston to Simpson Bay

Cheapest flights from Boston to Simpson Bay
Explore the most affordable flight options available from Boston to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This United Airlines deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/95:30 amBOS - SXM
1 stop6h 59mUnited Airlines
Wed 8/133:55 pmSXM - BOS
1 stop8h 04mUnited Airlines
Deal found 6/11$322
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/165:35 amBOS - SXM
1 stop8h 21mDelta
Sat 8/233:21 pmSXM - BOS
1 stop9h 59mDelta
Deal found 6/10$335
This CheapOair deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/199:18 amBOS - SXM
1 stop27h 07mMultiple Airlines
Fri 9/263:27 pmSXM - BOS
1 stop9h 12mMultiple Airlines
Deal found 6/11$359
This Cheapflightsfares deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/126:10 amBOS - SXM
1 stop7h 50mSpirit Airlines
Wed 7/163:05 pmSXM - BOS
1 stop8h 43mSpirit Airlines
Deal found 6/10$377
This Priceline deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:18 amBOS - SXM
1 stop27h 07mFrontier
Sat 11/151:58 pmSXM - BOS
1 stop19h 35mFrontier
Deal found 6/12$403
This JetBlue deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/237:50 amBOS - SXM
Nonstop4h 10mJetBlue
Sat 8/301:25 pmSXM - BOS
Nonstop4h 26mJetBlue
Deal found 6/10$409
This Air Canada deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/193:20 pmBOS - SXM
1 stop21h 35mAir Canada
Thu 11/273:05 pmSXM - BOS
1 stop26h 53mAir Canada
Deal found 6/11$413
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/189:06 pmBOS - SXM
2 stops17h 59mAmerican Airlines
Tue 7/224:25 pmSXM - BOS
2 stops17h 53mAmerican Airlines
Deal found 6/12$428

Cheapflights Fare Finder

Customize your flight search to find flights from Boston to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
Use the filters below to find and compare flights from Boston to Simpson Bay that are best for you.

Fly from

Boston

Fly to

Simpson Bay

Route

Depart

Return

Price

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/9

5:30 am-12:29 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Wed 8/13

3:55 pm-11:59 pm

1 stop8h 04m

$322

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/16

5:35 am-1:56 pm

1 stop8h 21m

Simpson Bay Princess Juliana

Sat 8/23

3:21 pm-1:20 am

1 stop9h 59m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 9/10

6:10 am-2:24 pm

1 stop8h 14m

Simpson Bay Princess Juliana

Sat 9/20

1:58 pm-8:33 am

1 stop18h 35m

$366

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 7/12

6:10 am-2:00 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Wed 7/16

3:05 pm-11:48 pm

1 stop8h 43m

$377

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 8/23

7:50 am-12:00 pm

Nonstop4h 10m

Simpson Bay Princess Juliana

Sat 8/30

1:25 pm-5:51 pm

Nonstop4h 26m

$409

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Tue 6/24

5:15 am-3:05 pm

1 stop9h 50m

Simpson Bay Princess Juliana

Thu 7/24

2:50 pm-12:59 am

1 stop10h 09m

$423

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/6

6:00 am-12:29 pm

1 stop6h 29m

$138

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 6/20

9:40 am-11:26 am

1 stop25h 46m

$183

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 9/6

5:18 pm-1:19 pm

2 stops20h 01m

$197

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Thu 7/31

8:35 pm-2:00 pm

2 stops17h 25m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 11 results
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Best time to book a flight from Boston to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Boston with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

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

Use this chart to determine the optimal time to book a round-trip flight from Boston to Simpson Bay. Price data was last updated on June 9, 2025.

To ensure you get the cheapest price possible for a flight from Boston to Simpson Bay, you should look to book at least 13 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Boston to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Boston to Simpson Bay (average of $459). Flying from Boston to Simpson Bay in March is currently the most expensive (average of $657). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to SXM?

Find hourly flight availability from Boston to Simpson Bay. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

When flying from Boston to Simpson Bay, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 57% versus a flight in the morning.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated June 12, 2025.
Read reviews from past customers who have flown Delta, United Airlines and JetBlue from Boston to Simpson Bay. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,790 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,925 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Spirit Airlines
6.3
Okay
8,052 reviews
Delta
8.0
Very good
7,950 reviews

Overall

8.0

Entertainment

7.9

Food

7.3

Boarding

8.2

Comfort

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Boston to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Boston to Simpson Bay round-trip?

    According to our current data, United Airlines ($322), Delta ($335), and Spirit Airlines ($377) offers the cheapest pricing from Boston to Simpson Bay. United Airlines is priced at 47% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Boston to Simpson Bay one-way?

    One-way options have recently been found by users for as low as $138 on United Airlines. Other airlines that offer cheap prices include Frontier from $183 and American Airlines from $197 one-way.

  • What are the cheapest flights from Boston to Simpson Bay?

    On average you can expect to pay $467 for a flight from Boston to Simpson Bay. The cheapest flight overall is $186 while the most popular route, (Boston Logan Intl - Simpson Bay Princess Juliana) is currently priced at $322.

  • Where are the most common layover locations when flying from Boston to Simpson Bay?

    Of the flights from Boston to Simpson Bay that have layovers, most of them stop in Miami. New York sees the next most layovers on Boston to Simpson Bay flights.

  • What are some popular things to do or see while on a layover in Miami?

    Wynwood Art District, Bayfront Park, and Bayside Marketplace are the most popular attractions in Miami if you're in need of something to do during your layover. Travelers on a layover in Miami can visit Wynwood Art District, Bayfront Park, and Bayside Marketplace, by traveling 5.5 mi, 6.4 mi, and 6.4 mi, respectively after landing at Miami. Travelers can book a car rental at Miami for about $21 per day to make their sightseeing more efficient.

  • What are some popular points of interest to see during a layover in New York?

    Times Square, New York City Center, and Madison Square Garden are the most popular attractions in New York if you're in need of something to do during your layover. Times Square, New York City Center, and Madison Square Garden are located about 13.6 mi, 13.6 mi, and 13.6 mi, respectively from New York John F Kennedy Intl. Travelers can book a car rental at New York John F Kennedy Intl for about $68 per day to make their sightseeing more efficient.

  • Where are the least popular layover locations for Boston to Simpson Bay flights?

    Boston to Simpson Bay flights have a layover in Fort Lauderdale least often.

  • Can I find deals for flights from Boston to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Boston to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Boston to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Simpson Bay.

  • Can I find deals for business class flights from Boston to Simpson Bay?

    Yes. Cheapflights offers flight deals from Boston to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, September is the cheapest month in which you can book a flight from Boston to Simpson Bay (average of $459). Flying from Boston to Simpson Bay in March is currently the most expensive (average of $657). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Boston to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Hartford to Simpson Bay flights
Albany to Simpson Bay flights
Worcester to Simpson Bay flights

Top 6 airlines flying from Boston to Simpson Bay

Discover the top 6 airlines that operate flights from Boston to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$73Average$227FlexibilityNo cancel feeOn-time62%
DeltaCheapest$174Average$444FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$317Average$552FlexibilityNo cancel feeOn-time69%
Spirit AirlinesCheapest$348Average$749FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$353Average$679FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$387Average$598FlexibilityNo cancel feeOn-time71%

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