HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$299+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SXM
Jan 16 — Jan 231
Fri 1/16
Fri 1/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Worcester 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 Worcester to Simpson Bay

Best flights from Worcester to Simpson Bay
Discover carefully curated flight deals from Worcester to Simpson Bay that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 17, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/292:18 pmORH - SXM
1 stop23h 13mAmerican Airlines
Thu 2/55:33 pmSXM - ORH
2 stops21h 20mAmerican Airlines
Deal found 12/15$299

Find 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 December 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$299
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$626
Provider with most accurate pricing for Worcester-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Worcester-Simpson Bay Princess Juliana flights.
Search Deals
From Worcester to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 17, 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

Thu 1/29

2:18 pm-2:31 pm

1 stop23h 13m

Simpson Bay Princess Juliana

Thu 2/5

5:33 pm-1:53 pm

2 stops21h 20m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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 December.
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 $299, American Airlines can have you in Simpson Bay from Worcester, Massachusetts in 23h 13m. 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Worcester to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Simpson Bay flights
Hartford to Simpson Bay flights
Albany to Simpson Bay flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.