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Simpson Bay

$150+ Cheap flights from Road Town (EIS) 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 6/18. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SXM
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
1 adult, Economy
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Cheap flight deals from Road Town to Simpson Bay

Cheapest flights from Road Town to Simpson Bay
Explore the most affordable flight options available from Road Town to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 5, 2026.

This Booking.com deal was found by Cheapflights users on 2/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:45 pm
EIS
-
SXM
Nonstop0h 40m
Multiple Airlines
Sat 10/3110:20 am
SXM
-
EIS
Nonstop0h 45m
Multiple Airlines
Deal found 2/4$384
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:35 am
EIS
-
SXM
1 stop2h 25m
Winair
Sat 10/315:15 pm
SXM
-
EIS
1 stop1h 50m
Winair
Deal found 2/4$402
This FlightHub deal was found by Cheapflights users on 2/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/67:50 pm
EIS
-
SXM
Nonstop0h 45m
Winair
Mon 3/95:15 pm
SXM
-
EIS
1 stop1h 50m
Winair
Deal found 2/2$412
This CheapOair deal was found by Cheapflights users on 2/3. 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.
Thu 3/1211:35 am
EIS
-
SXM
1 stop2h 25m
Winair
Mon 3/165:00 pm
SXM
-
EIS
1 stop25h 40m
Winair
Deal found 2/3$413
This FlightHub deal was found by Cheapflights users on 2/5. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/207:50 pm
EIS
-
SXM
Nonstop0h 45m
Winair
Thu 2/265:00 pm
SXM
-
EIS
1 stop2h 25m
Winair
Deal found 2/5$442
This FlightHub deal was found by Cheapflights users on 2/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:50 pm
EIS
-
SXM
Nonstop0h 45m
Winair
Sun 3/1510:20 am
SXM
-
EIS
Nonstop0h 45m
Winair
Deal found 2/4$452
This Booking.com deal was found by Cheapflights users on 2/4. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/168:00 am
EIS
-
SXM
Nonstop0h 50m
Winair
Mon 2/165:15 pm
SXM
-
EIS
1 stop1h 50m
Winair
Deal found 2/4$466
This CheapOair deal was found by Cheapflights users on 2/2. 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 4/1711:35 am
EIS
-
SXM
1 stop2h 25m
Multiple Airlines
Mon 4/209:05 am
SXM
-
EIS
2 stops26h 05m
Multiple Airlines
Deal found 2/2$516

Find flight deals from Road Town to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Road Town (EIS) 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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$412
(FlightHub)

One-way from

$150
(Mytrip)

Popular in

January

Cheapest in

September

Average price

$379
Provider with most accurate pricing for Road Town Beef Island-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Road Town Beef Island-Simpson Bay Princess Juliana flights.
Search Deals
From Road Town Beef Island to Simpson Bay Princess Juliana
Search Deals
One-way flight from Road Town Beef Island to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Road Town 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 February 5, 2026.
Use the filters below to find and compare flights from Road Town to Simpson Bay that are best for you.

Fly from

Road Town

Fly to

Simpson Bay

Route

Depart

Return

Price

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 3/13

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Sun 3/15

5:00 pm-7:25 pm

1 stop2h 25m

$412

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 3/6

7:50 pm-8:35 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Mon 3/9

10:20 am-11:05 am

Nonstop0h 45m

$412

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 3/12

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Mon 3/16

5:00 pm-6:40 pm

1 stop25h 40m

$412

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 2/20

7:50 pm-8:35 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Thu 2/26

10:20 am-11:05 am

Nonstop0h 45m

$412

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 3/27

11:35 am-9:20 am

1 stop21h 45m

Simpson Bay Princess Juliana

Mon 3/30

10:20 am-11:05 am

Nonstop0h 45m

$412

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 6/18

1:45 pm-2:25 pm

Nonstop0h 40m

$150

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Tue 2/10

11:35 am-9:20 am

1 stop21h 45m

$169

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 2/15

7:15 am-9:05 am

1 stop1h 50m

$173

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Wed 3/4

11:35 am-9:20 am

1 stop21h 45m

$175

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 6/18

11:35 am-2:00 pm

1 stop2h 25m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 13 results
1
2

Compare providers for flights from Road Town to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Road Town to Simpson Bay in February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Road Town-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Road Town-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Road Town-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Road Town-Simpson Bay flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Road Town-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Road Town to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Road Town 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 Road Town to Simpson Bay

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

Currently, April is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $228). Flying from Road Town to Simpson Bay in January is currently the most expensive (average of $385). 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 EIS to SXM?

Find hourly flight availability from Road Town 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 February 5, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 44% on flights from Road Town to Simpson Bay by exploring options for tickets in the morning.

How much does it cost to fly round-trip from Road Town to Simpson Bay?

Related info for your journey

Find useful and relevant information for your journey from Road Town 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 airports do I use to fly from Road Town to Simpson Bay?

    Simpson Bay Princess Juliana is the airport most travelers will use when flying to Simpson Bay from Road Town Beef Island. Booking flights from Beef Island (EIS) to Princess Juliana (SXM) should be relatively easy as there is 1 daily flight to Simpson Bay from 1 airline. 23h 55m is how long a flight from Road Town to Simpson Bay Princess Juliana will take if you book a nonstop flight.

  • How popular is this Road Town to Simpson Bay flight route?

    Within the past month, 3 users have taken a look at flights from Road Town Beef Island to Simpson Bay Princess Juliana.

  • How long is the flight from Road Town to Simpson Bay?

    Departing from Road Town to Simpson Bay will take you 21h 45m. Airlines will cover a distance of 98 mi.

  • What is the cheapest airline to fly from Road Town to Simpson Bay round-trip?

    Flying on Winair is currently your cheapest option to Simpson Bay, with prices starting at $336. Winair is priced at 12% lower than the current average price of a flight leaving 3 months from now.

  • What are the most reliable airlines from Road Town to Simpson Bay?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Road Town to Simpson Bay on time: Fly Salone (100%), KLM (82%), Air France (82%).

  • What are the cheapest flights from Road Town to Simpson Bay?

    Looking at all options, your cheapest flight can be booked for $187. While the most popular route (Road Town Beef Island - Simpson Bay Princess Juliana) can be booked for $8,265 on average, our data indicates $332 when flying from Road Town to Simpson Bay.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Road Town 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 Road Town to Simpson Bay?

    Currently, April is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $228). Flying from Road Town to Simpson Bay in January is currently the most expensive (average of $385). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Browse thousands of different options on Cheapflights for your next trip

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Complete your trip

Complete your trip to Simpson Bay by adding a car rental and/or hotel reservation to your travel itinerary.
Simpson Bay Princess Juliana Airport car rentals

Top airline flying from Road Town to Simpson Bay

Discover the top airline that operate flights from Road Town 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 February 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
WinairCheapest$336Average$384FlexibilityNo cancel feeOn-timeN/A

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