$148+ Cheap flights from Road Town (EIS) to Simpson Bay (SXM)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
EIS — SXM
Nov 30 — Dec 71
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
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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 October 31, 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 October 31, 2026.
This Mytrip deal was found by Cheapflights users on 10/26. 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 12/241:45 pm -
Nonstop0h 40m
Sun 12/2710:30 am -
Nonstop0h 40m
Deal found 10/26![Multiple Airlines logo]()
$359
This CheapOair deal was found by Cheapflights users on 10/27. 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 11/67:15 am -
1 stop1h 55m
Sun 11/89:55 am -
Nonstop0h 50m
Deal found 10/27![Multiple Airlines logo]()
$461
This FlightHub deal was found by Cheapflights users on 10/26. 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.
Thu 12/101:45 pm -
Nonstop0h 40m
Thu 12/1710:20 am -
Nonstop0h 45m
Deal found 10/26![Multiple Airlines logo]()
$463
This Booking.com deal was found by Cheapflights users on 10/27. 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 10/3011:35 am -
1 stop22h 25m
Sun 11/11:25 pm -
Nonstop0h 40m
Deal found 10/27![Multiple Airlines logo]()
$464
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 12/137:15 am -
1 stop1h 55m
Tue 12/1510:20 am -
Nonstop0h 45m
Deal found 10/27![Winair logo]()
$476
This Booking.com deal was found by Cheapflights users on 10/27. 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 10/307:15 am -
1 stop6h 35m
Sat 10/3110:20 am -
Nonstop0h 45m
Deal found 10/27![Winair logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/108:20 am -
1 stop1h 55m
Tue 11/1710:20 am -
Nonstop0h 45m
Deal found 10/27![Winair logo]()
$484
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1111:45 am -
1 stop2h 30m
Thu 11/1210:20 am -
Nonstop0h 45m
Deal found 10/27![Winair logo]()
$486
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 10/307:15 am -
1 stop1h 55m
Sun 11/15:15 pm -
1 stop2h 30m
Deal found 10/27![Winair logo]()
$497
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 October 31, 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 October 31, 2026.
This CheapOair deal was found by Cheapflights users on 10/29. 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.
Tue 2/911:35 am -
1 stop2h 30m
Fri 2/1210:45 am -
Nonstop0h 40m
Deal found 10/29![Multiple Airlines logo]()
$443
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 4/1611:35 am -
1 stop2h 30m
Mon 4/1910:20 am -
Nonstop0h 45m
Deal found 10/25![Winair logo]()
$482
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/108:20 am -
1 stop1h 55m
Tue 11/1710:20 am -
Nonstop0h 45m
Deal found 10/27![Winair logo]()
$484
This Justfly.com deal was found by Cheapflights users on 10/29. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/911:35 am -
1 stop2h 30m
Fri 2/125:15 pm -
1 stop2h 30m
Deal found 10/29![Winair logo]()
$521
This Winair deal was found by Cheapflights users on 10/28. 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.
Fri 11/137:15 am -
1 stop1h 55m
Tue 11/1710:20 am -
Nonstop0h 45m
Deal found 10/28![Winair logo]()
$534
Last-minute flights from Road Town to Simpson BayDiscover last-minute flight deals from Road Town to Simpson Bay. Data last updated October 31, 2026 and is based on user searches.
Discover last-minute flight deals from Road Town to Simpson Bay. Data last updated October 31, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 10/27. 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 11/67:15 am -
1 stop1h 55m
Sun 11/89:55 am -
Nonstop0h 50m
Deal found 10/27![Multiple Airlines logo]()
$461
This FlightHub deal was found by Cheapflights users on 10/27. 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 11/611:35 am -
1 stop22h 25m
Sun 11/85:15 pm -
1 stop2h 30m
Deal found 10/27![Winair logo]()
$554
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 October 31, 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 October 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/27. 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
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![interCaribbean Airways logo]()
$148
This interCaribbean Airways deal was found by Cheapflights users on 10/27. 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 interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/191:45 pm -
Nonstop0h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![interCaribbean Airways logo]()
$184
This interCaribbean Airways deal was found by Cheapflights users on 10/27. 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 interCaribbean Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/171:45 pm -
Nonstop0h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![interCaribbean Airways logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/911:35 am -
1 stop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Winair logo]()
$217
This Winair deal was found by Cheapflights users on 10/27. 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.
Mon 12/2111:35 am -
1 stop21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Winair logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 12/1711:35 am -
1 stop2h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Winair logo]()
$239
This Winair deal was found by Cheapflights users on 10/27. 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 12/1911:35 am -
1 stop21h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Winair logo]()
$255
This FlightHub deal was found by Cheapflights users on 10/27. 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.
Thu 12/248:50 am -
2 stops25h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$278
This FlightHub deal was found by Cheapflights users on 10/27. 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 12/198:50 am -
2 stops24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/27![Multiple Airlines logo]()
$286
This CheapOair deal was found by Cheapflights users on 10/30. 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.
Mon 11/911:35 am -
2 stops23h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Multiple Airlines logo]()
$310
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 October 31, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $359 (Mytrip) |
One-way from | $148 (Kiwi.com) |
Popular in | September |
Cheapest in | July |
Average price | $447 |
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 October 31, 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
Mon 12/21
11:35 am-9:30 am
1 stop21h 55m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$235
Quickest round-trip
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Mon 11/9
8:00 am-8:40 am
Nonstop0h 40m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$240
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Sat 12/19
11:35 am-9:30 am
1 stop21h 55m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$255
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Mon 11/9
11:35 am-10:45 am
2 stops23h 10m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$310
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Thu 12/17
11:35 am-8:20 am
2 stops20h 45m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$392
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Tue 2/9
11:35 am-2:05 pm
1 stop2h 30m
Simpson Bay Princess Juliana
Fri 2/12
10:45 am-11:25 am
Nonstop0h 40m
$443
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Fri 4/16
11:35 am-2:05 pm
1 stop2h 30m
Simpson Bay Princess Juliana
Mon 4/19
10:20 am-11:05 am
Nonstop0h 45m
$482
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Tue 11/10
8:20 am-10:15 am
1 stop1h 55m
Simpson Bay Princess Juliana
Tue 11/17
10:20 am-11:05 am
Nonstop0h 45m
$484
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Tue 2/9
11:35 am-2:05 pm
1 stop2h 30m
Simpson Bay Princess Juliana
Fri 2/12
5:15 pm-7:45 pm
1 stop2h 30m
$521
Road TownSimpson Bay
EIS Road Town Beef Island - SXM Simpson Bay Princess Juliana
EISSXM
Road Town Beef Island
Tue 12/22
8:50 am-12:40 pm
2 stops27h 50m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$525
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 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, July is the cheapest month in which you can book a flight from Road Town to Simpson Bay (average of $360). Flying from Road Town to Simpson Bay in September is currently the most expensive (average of $486). 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 October 31, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 11% on flights from Road Town to Simpson Bay by exploring options for tickets in the afternoon.
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 October 31, 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.
Food
4.4
Entertainment
4.6
Overall
5.7
Comfort
5.6
Boarding
5.4
Crew
6.5
Reviews
1 / 1
2.0
MediocreDabian,Aug 2024
BGI - SLU
Food
4.4
Entertainment
4.6
Overall
5.7
Comfort
5.6
Boarding
5.4
Crew
6.5
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 October 31, 2026.
Popular flight searches
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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 October 31, 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 October 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$143 | Average$330 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$305 | Average$429 | FlexibilityNo cancel fee | On-timeN/A |