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Simpson Bay

$152+ 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 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SXM
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
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Cheap 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 September 14, 2025.

Round-trip from

$352
(Gotogate)

One-way from

$152
(Mytrip)

Popular in

October

Cheapest in

July

Average price

$369
From Road Town Beef Island to Simpson Bay Princess Juliana
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One-way flight from Road Town Beef Island to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 14, 2025.

This Gotogate deal was found by Cheapflights users on 9/12. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:35 amEIS - SXM
1 stop21h 45mWinair
Sun 12/710:20 amSXM - EIS
Nonstop0h 45mWinair
Deal found 9/12$352
This Booking.com deal was found by Cheapflights users on 9/14. 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 10/47:35 pmEIS - SXM
Nonstop0h 45mWinair
Mon 10/65:00 pmSXM - EIS
1 stop25h 35mWinair
Deal found 9/14$356
This Booking.com deal was found by Cheapflights users on 9/14. 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.
Thu 11/611:35 amEIS - SXM
1 stop2h 25mWinair
Mon 11/105:15 pmSXM - EIS
1 stop1h 50mWinair
Deal found 9/14$357
This Booking.com deal was found by Cheapflights users on 9/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1511:35 amEIS - SXM
1 stop2h 25mWinair
Wed 10/155:00 pmSXM - EIS
1 stop25h 35mWinair
Deal found 9/11$362
This CheapOair deal was found by Cheapflights users on 9/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1211:55 amEIS - SXM
1 stop2h 25mWinair
Tue 12/1610:20 amSXM - EIS
Nonstop0h 45mWinair
Deal found 9/12$366
This Winair deal was found by Cheapflights users on 9/13. 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 Winair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:15 amEIS - SXM
1 stop1h 50mWinair
Fri 9/264:15 pmSXM - EIS
1 stop2h 20mWinair
Deal found 9/13$386
This Winair deal was found by Cheapflights users on 9/13. 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 Winair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/187:05 pmEIS - SXM
Nonstop0h 45mWinair
Mon 9/2910:40 amSXM - EIS
Nonstop0h 45mWinair
Deal found 9/13$396
This Winair deal was found by Cheapflights users on 9/13. 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 Winair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:15 amEIS - SXM
1 stop1h 50mWinair
Thu 9/2510:30 amSXM - EIS
Nonstop0h 50mWinair
Deal found 9/13$406

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 September 14, 2025.
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 12/26

11:55 am-9:20 am

1 stop21h 25m

Simpson Bay Princess Juliana

Tue 12/30

10:20 am-11:05 am

Nonstop0h 45m

$356

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 10/4

7:35 pm-8:20 pm

Nonstop0h 45m

Simpson Bay Princess Juliana

Mon 10/6

5:00 pm-6:35 pm

1 stop25h 35m

$356

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Tue 10/14

11:35 am-9:30 am

1 stop21h 55m

Simpson Bay Princess Juliana

Tue 10/21

10:20 am-11:05 am

Nonstop0h 45m

$356

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 12/14

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Wed 12/17

5:00 pm-6:40 pm

1 stop25h 40m

$356

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Thu 11/6

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Mon 11/10

5:15 pm-7:05 pm

1 stop1h 50m

$357

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Wed 10/15

11:35 am-2:00 pm

1 stop2h 25m

Simpson Bay Princess Juliana

Wed 10/15

5:00 pm-6:35 pm

1 stop25h 35m

$362

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Tue 10/14

11:35 am-9:30 am

1 stop21h 55m

$152

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sun 10/12

11:35 am-2:00 pm

1 stop2h 25m

$156

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Fri 1/16

11:55 am-9:20 am

1 stop21h 25m

$163

Road TownSimpson Bay

EIS - SXM

EISSXM

Road Town Beef Island

Sat 10/11

11:35 am-2:00 pm

1 stop2h 25m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 11 results
1
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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, September is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $459). Flying from Road Town to Simpson Bay in March is currently the most expensive (average of $652). 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 September 14, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 16% on flights from Road Town to Simpson Bay by exploring options for tickets in the afternoon.

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.

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

    Within the past month, 1 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 25m. 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 $333. Winair is priced at 11% 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: Winair (91%), KLM (70%), Air France (70%).

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

    Looking at all options, your cheapest flight can be booked for $173. While the most popular route (Road Town Beef Island - Simpson Bay Princess Juliana) can be booked for $8,265 on average, our data indicates $272 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, September is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $459). Flying from Road Town to Simpson Bay in March is currently the most expensive (average of $652). 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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
WinairCheapest$333Average$374FlexibilityNo cancel feeOn-timeN/A

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