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Simpson Bay

$531+ Cheap flights from Worcester, MA (ORH) 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Worcester to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Worcester (ORH) 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 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$531
(American Airlines)

Popular in

February

Cheapest in

September

Average price

$558
Provider with most accurate pricing for Worcester-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Worcester-Simpson Bay Princess Juliana flights.
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From Worcester to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 6% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Worcester to Simpson Bay

Cheapest flights from Worcester to Simpson Bay
Explore the most affordable flight options available from Worcester to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 30, 2025.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:47 pmORH - SXM
1 stop22h 39mAmerican Airlines
Sat 1/35:04 pmSXM - ORH
2 stops21h 13mAmerican Airlines
Deal found 10/28$1,578

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester 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 October 30, 2025.
Use the filters below to find and compare flights from Worcester to Simpson Bay that are best for you.

Fly from

Worcester

Fly to

Simpson Bay

Route

Depart

Return

Price

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Mon 4/6

3:25 pm-12:45 pm

2 stops21h 20m

Simpson Bay Princess Juliana

Wed 4/8

5:25 pm-2:53 pm

2 stops45h 28m

$531

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

Sat 12/27

1:47 pm-1:26 pm

1 stop22h 39m

Simpson Bay Princess Juliana

Sat 1/3

5:04 pm-1:17 pm

2 stops21h 13m

$1,578

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Compare providers for flights from Worcester 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 Worcester to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Worcester, Massachusetts-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Worcester, Massachusetts-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Worcester, Massachusetts-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams 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 Worcester, Massachusetts-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 Worcester to Simpson Bay

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

What is the cheapest month to book a flight from Worcester, Massachusetts to Simpson Bay?

Currently, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Simpson Bay (average of $143). Flying from Worcester, Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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.

Related info for your journey

Find useful and relevant information for your journey from Worcester 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 Worcester, Massachusetts to Simpson Bay?

    For as low as $531, American Airlines can have you in Simpson Bay from Worcester, Massachusetts in 21h 20m. Airlines will cover a distance of 1750 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Worcester 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 Worcester, Massachusetts to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Worcester, Massachusetts to Simpson Bay (average of $143). Flying from Worcester, Massachusetts to Simpson Bay in June is currently the most expensive (average of $372). 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

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