$132+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SXM
Sep 18 — Sep 251
Round-trip
1 adult, Economy
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Find cheap flights from Road Town to Simpson Bay with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Road Town to Simpson Bay
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Best
Last-minute
One-way
Cheapest flights from Road Town to Simpson BayExplore 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 August 19, 2026.
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 August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:45 pm -
Nonstop0h 40m
Sun 9/2010:20 am -
Nonstop0h 50m
Deal found 8/16![Multiple Airlines logo]()
$340
This Mytrip deal was found by Cheapflights users on 8/15. 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.
Thu 10/221:45 pm -
Nonstop0h 40m
Sun 10/251:25 pm -
Nonstop0h 40m
Deal found 8/15![interCaribbean Airways logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:25 am -
1 stop22h 05m
Wed 9/1610:20 am -
Nonstop0h 50m
Deal found 8/17![Winair logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:50 am -
Nonstop0h 45m
Sun 10/255:15 pm -
1 stop2h 30m
Deal found 8/15![Winair logo]()
$393
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:45 pm -
Nonstop0h 40m
Sat 10/35:15 pm -
1 stop2h 00m
Deal found 8/17![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/241:45 pm -
Nonstop0h 40m
Sat 1/210:20 am -
Nonstop0h 45m
Deal found 8/17![Multiple Airlines logo]()
$398
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/259:55 am -
Nonstop0h 40m
Sun 9/271:25 pm -
Nonstop0h 40m
Deal found 8/17![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2411:35 am -
1 stop2h 30m
Sat 1/25:15 pm -
1 stop2h 00m
Deal found 8/17![Winair logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:00 am -
Nonstop0h 45m
Wed 9/910:20 am -
Nonstop0h 50m
Deal found 8/17![Winair logo]()
$413
Best flights from Road Town to Simpson BayDiscover carefully curated flight deals from Road Town to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
Discover carefully curated flight deals from Road Town to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:45 pm -
Nonstop0h 40m
Sat 10/35:15 pm -
1 stop2h 00m
Deal found 8/17![Multiple Airlines logo]()
$396
This CheapOair deal was found by Cheapflights users on 8/16. 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.
Sat 9/127:45 pm -
Nonstop0h 50m
Tue 9/1510:20 am -
Nonstop0h 50m
Deal found 8/16![Winair logo]()
$439
This CheapOair deal was found by Cheapflights users on 8/19. 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 9/119:55 am -
Nonstop0h 40m
Tue 9/1510:20 am -
Nonstop0h 50m
Deal found 8/19![Winair logo]()
$459
This CheapOair deal was found by Cheapflights users on 8/15. 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 10/227:15 am -
1 stop6h 20m
Sun 10/251:00 pm -
2 stops6h 45m
Deal found 8/15![Multiple Airlines logo]()
$480
Last-minute flights from Road Town to Simpson BayDiscover last-minute flight deals from Road Town to Simpson Bay. Data last updated August 19, 2026 and is based on user searches.
Discover last-minute flight deals from Road Town to Simpson Bay. Data last updated August 19, 2026 and is based on user searches.
This Booking.com deal was found by Cheapflights users on 8/16. 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 8/201:45 pm -
Nonstop0h 40m
Sat 8/225:15 pm -
1 stop2h 00m
Deal found 8/16![Multiple Airlines logo]()
$433
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/28:00 am -
Nonstop0h 45m
Wed 9/910:20 am -
Nonstop0h 50m
Deal found 8/17![Winair logo]()
$413
This Booking.com deal was found by Cheapflights users on 8/17. 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 9/211:25 am -
1 stop22h 05m
Wed 9/91:25 pm -
Nonstop0h 40m
Deal found 8/17![Multiple Airlines logo]()
$428
This CheapOair deal was found by Cheapflights users on 8/16. 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.
Sat 9/127:15 am -
1 stop1h 55m
Tue 9/1510:20 am -
Nonstop0h 50m
Deal found 8/16![Winair logo]()
$439
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1411:25 am -
1 stop22h 05m
Wed 9/1610:20 am -
Nonstop0h 50m
Deal found 8/17![Winair logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/171:45 pm -
Nonstop0h 40m
Sun 9/2010:20 am -
Nonstop0h 50m
Deal found 8/16![Multiple Airlines logo]()
$340
This Booking.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/259:55 am -
Nonstop0h 40m
Sun 9/271:25 pm -
Nonstop0h 40m
Deal found 8/17![Multiple Airlines logo]()
$399
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:55 am -
Nonstop0h 40m
Wed 9/305:15 pm -
1 stop2h 00m
Deal found 8/18![Winair logo]()
$436
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/261:45 pm -
Nonstop0h 40m
Sat 10/35:15 pm -
1 stop2h 00m
Deal found 8/17![Multiple Airlines logo]()
$396
One-way flights from Road Town to Simpson BaySearch for one-way flight options from Road Town to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
Search for one-way flight options from Road Town to Simpson Bay. Find affordable one-way fares based on user searches. Data last updated August 19, 2026.
This FlightHub deal was found by Cheapflights users on 8/19. 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.
Sat 9/264:00 pm -
Nonstop0h 40m
Deal found 8/19![Hahn Air logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/301:45 pm -
Nonstop0h 40m
Deal found 8/17![interCaribbean Airways logo]()
$150
This Mytrip deal was found by Cheapflights users on 8/16. 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 8/291:45 pm -
Nonstop0h 40m
Deal found 8/16![interCaribbean Airways logo]()
$168
This FlightHub deal was found by Cheapflights users on 8/17. 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.
Sat 9/261:45 pm -
Nonstop0h 40m
Deal found 8/17![interCaribbean Airways logo]()
$174
This Booking.com deal was found by Cheapflights users on 8/15. 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 10/2411:25 am -
1 stop22h 05m
Deal found 8/15![Winair logo]()
$182
This Booking.com deal was found by Cheapflights users on 8/17. 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 1/3011:35 am -
1 stop21h 55m
Deal found 8/17![Winair logo]()
$183
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Fri 8/289:50 am -
Nonstop0h 50m
Deal found 8/19![Winair logo]()
$187
This Booking.com deal was found by Cheapflights users on 8/16. 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 8/297:15 am -
1 stop9h 20m
Deal found 8/16![Winair logo]()
$192
This FlightHub deal was found by Cheapflights users on 8/17. 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.
Sat 9/267:15 am -
1 stop1h 55m
Deal found 8/17![Winair logo]()
$195
This Booking.com deal was found by Cheapflights users on 8/18. 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 10/1911:25 am -
1 stop22h 05m
Deal found 8/18![Winair logo]()
$232
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 August 19, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $340 (Kiwi.com) |
One-way from | $132 (FlightHub) |
Popular in | April |
Cheapest in | June |
Average price | $362 |
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 7,457,451 searches. Data last updated August 19, 2026.
Use the filters below to find and compare flights from Road Town to Simpson Bay that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 9/26
1:45 pm-2:25 pm
Nonstop0h 40m
Simpson Bay Princess Juliana
Sat 10/3
5:15 pm-7:15 pm
1 stop2h 00m
$396
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 9/12
7:45 pm-8:35 pm
Nonstop0h 50m
Simpson Bay Princess Juliana
Tue 9/15
10:20 am-11:10 am
Nonstop0h 50m
$439
Quickest round-trip
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Fri 9/11
9:55 am-10:35 am
Nonstop0h 40m
Simpson Bay Princess Juliana
Tue 9/15
10:20 am-11:10 am
Nonstop0h 50m
$459
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Thu 10/22
7:15 am-1:35 pm
1 stop6h 20m
Simpson Bay Princess Juliana
Sun 10/25
1:00 pm-7:45 pm
2 stops6h 45m
$480
Cheapest one-way
Quickest one-way
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 9/26
4:00 pm-4:40 pm
Nonstop0h 40m
$132
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 1/30
1:45 pm-2:25 pm
Nonstop0h 40m
$150
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 9/26
1:45 pm-2:25 pm
Nonstop0h 40m
$174
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Tue 1/5
11:35 am-9:30 am
1 stop21h 55m
$182
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 10/24
11:25 am-9:30 am
1 stop22h 05m
$182
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 1/30
11:35 am-9:30 am
1 stop21h 55m
$183
Showing 1-10 of 13 resultsSorted by cheapest first
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 August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
EIS-SXM
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
Prices
Airlines
What is the cheapest month to book a flight from Road Town to Simpson Bay?
Currently, June is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $267). Flying from Road Town to Simpson Bay in April is currently the most expensive (average of $452). 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 August 19, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 15% on flights from Road Town to Simpson Bay by exploring options for tickets at noon.
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 August 19, 2026.
Read reviews from past customers who have flown interCaribbean Airways from Road Town to Simpson Bay. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
5.5
Crew
6.4
Overall
5.8
Food
4.6
Entertainment
4.7
Comfort
5.6
Reviews
1 / 1
2.0
MediocreDabian,Aug 2024
BGI - SLU
Boarding
5.5
Crew
6.4
Overall
5.8
Food
4.6
Entertainment
4.7
Comfort
5.6
Reviews
1 / 1
2.0
MediocreDabian,Aug 2024
BGI - SLU
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.
Traveling to a place near Simpson Bay?
Book flights to Simpson Bay if you plan to visit one of these locationsPhilipsburg
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Road Town and Simpson Bay flights
Browse other Road Town and Simpson Bay flight options. Last updated on August 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Simpson Bay
Explore flights to Simpson Bay departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 19, 2026.
Top 2 airlines flying from Road Town to Simpson Bay
Discover the top 2 airlines 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 7,457,451 searches. Data last updated August 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$326 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$305 | Average$403 | FlexibilityNo cancel fee | On-timeN/A |