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Simpson Bay

$355+ Cheap flights from Roanoke (ROA) 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 4/16. Fares are subject to change and may not be available on all flights or dates of travel.
ROA — SXM
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
1 adult, Economy
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Cheap flight deals from Roanoke to Simpson Bay

Cheapest flights from Roanoke to Simpson Bay
Explore the most affordable flight options available from Roanoke to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.

This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:00 pm
ROA
-
SXM
2 stops19h 22m
American Airlines
Sun 4/2612:41 pm
SXM
-
ROA
2 stops21h 57m
American Airlines
Deal found 2/13$355
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:00 pm
ROA
-
SXM
2 stops17h 16m
American Airlines
Sun 4/192:24 pm
SXM
-
ROA
1 stop9h 15m
American Airlines
Deal found 2/10$489
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:00 am
ROA
-
SXM
1 stop6h 21m
American Airlines
Sat 4/114:35 pm
SXM
-
ROA
2 stops19h 58m
American Airlines
Deal found 2/13$617
This United Airlines deal was found by Cheapflights users on 2/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:15 am
ROA
-
SXM
2 stops26h 35m
United Airlines
Thu 2/262:52 pm
SXM
-
ROA
2 stops20h 16m
United Airlines
Deal found 2/13$702
This United Airlines deal was found by Cheapflights users on 2/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/77:59 pm
ROA
-
SXM
1 stop16h 34m
United Airlines
Sat 4/113:50 pm
SXM
-
ROA
2 stops21h 39m
United Airlines
Deal found 2/10$796

Find flight deals from Roanoke to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Roanoke (ROA) 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 14, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$355
(American Airlines)
Provider with most accurate pricing for Roanoke-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Roanoke-Simpson Bay Princess Juliana flights.
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From Roanoke to Simpson Bay Princess Juliana
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Roanoke 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 14, 2026.
Use the filters below to find and compare flights from Roanoke to Simpson Bay that are best for you.

Fly from

Roanoke

Fly to

Simpson Bay

Route

Depart

Return

Price

RoanokeSimpson Bay

ROA - SXM

ROASXM

Roanoke

Thu 4/16

8:00 pm-1:16 pm

2 stops17h 16m

Simpson Bay Princess Juliana

Sun 4/26

4:35 pm-10:38 am

2 stops18h 03m

$355

RoanokeSimpson Bay

ROA - SXM

ROASXM

Roanoke

Wed 4/15

8:00 pm-3:22 pm

2 stops19h 22m

Simpson Bay Princess Juliana

Sun 4/19

12:41 pm-10:38 am

2 stops21h 57m

$355

RoanokeSimpson Bay

ROA - SXM

ROASXM

Roanoke

Tue 4/7

7:00 am-1:21 pm

1 stop6h 21m

Simpson Bay Princess Juliana

Sat 4/11

4:35 pm-12:33 pm

2 stops19h 58m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Compare providers for flights from Roanoke 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 Roanoke to Simpson Bay in February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 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 Roanoke-Simpson Bay flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Roanoke-Simpson Bay flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Roanoke-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Roanoke-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 Roanoke-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 Roanoke to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Roanoke 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.

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 February 14, 2026.
Get a feel of what it's like to fly with American Airlines from Roanoke to Simpson Bay by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,288 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,288 reviews
American Airlines
7.2
Good
11,288 reviews

Entertainment

6.9

Crew

8.0

Overall

7.2

Comfort

7.2

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Roanoke 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 long is the flight from Roanoke to Simpson Bay?

    American Airlines can get you from Roanoke to Simpson Bay in just under 17h 16m. Your travel time can differ by up to . The distance from Roanoke to Simpson Bay is about 1678 mi.

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

    American Airlines, at $576, was found to be the cheapest airline from Roanoke to Simpson Bay..

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Roanoke 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.

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

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Top airline flying from Roanoke to Simpson Bay

Discover the top airline that operate flights from Roanoke 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 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$576Average$904FlexibilityNo cancel feeOn-time71%

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