HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$360+ Cheap flights from Worcester, MA (ORH) 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — SXM
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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

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 septiembre 11, 2025.

Round-trip from

$979
(American Airlines)

One-way from

$360
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$460
From Worcester to Simpson Bay Princess Juliana
Search Deals
One-way flight from Worcester to Simpson Bay Princess Juliana
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 septiembre 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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.
dom. 11/233:17 pmORH - SXM
2 stops22h 02mAmerican Airlines
vie. 11/285:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$979
This American Airlines deal was found by Cheapflights users on 9/10. 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.
sáb. 11/223:17 pmORH - SXM
2 stops22h 02mAmerican Airlines
vie. 11/285:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$1,027
This American Airlines deal was found by Cheapflights users on 9/10. 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.
vie. 11/213:17 pmORH - SXM
2 stops23h 54mAmerican Airlines
vie. 11/285:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$1,052
This American Airlines deal was found by Cheapflights users on 9/10. 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.
dom. 11/233:17 pmORH - SXM
2 stops21h 33mAmerican Airlines
dom. 11/305:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$1,159
This American Airlines deal was found by Cheapflights users on 9/10. 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.
sáb. 11/223:17 pmORH - SXM
2 stops24h 05mAmerican Airlines
dom. 11/305:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$1,233
This American Airlines deal was found by Cheapflights users on 9/10. 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.
vie. 11/213:17 pmORH - SXM
2 stops23h 54mAmerican Airlines
dom. 11/305:24 pmSXM - ORH
2 stops22h 27mAmerican Airlines
Deal found 9/10$1,266

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 septiembre 11, 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

dom. 11/23

3:17 pm-2:19 pm

2 stops22h 02m

Simpson Bay Princess Juliana

vie. 11/28

5:24 pm-2:51 pm

2 stops22h 27m

$979

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

sáb. 11/22

3:17 pm-2:19 pm

2 stops22h 02m

Simpson Bay Princess Juliana

vie. 11/28

5:24 pm-2:51 pm

2 stops22h 27m

$1,027

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

vie. 11/21

3:17 pm-4:11 pm

2 stops23h 54m

Simpson Bay Princess Juliana

vie. 11/28

5:24 pm-2:51 pm

2 stops22h 27m

$1,052

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

dom. 11/23

3:17 pm-1:50 pm

2 stops21h 33m

Simpson Bay Princess Juliana

dom. 11/30

5:24 pm-2:51 pm

2 stops22h 27m

$1,159

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

vie. 11/21

3:17 pm-4:11 pm

2 stops23h 54m

Simpson Bay Princess Juliana

dom. 11/30

5:24 pm-2:51 pm

2 stops22h 27m

$1,266

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

dom. 10/19

4:17 pm-1:37 pm

2 stops21h 20m

$360

WorcesterSimpson Bay

ORH - SXM

ORHSXM

Worcester

lun. 10/20

4:17 pm-1:37 pm

2 stops21h 20m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 $459). Flying from Worcester, Massachusetts to Simpson Bay in March is currently the most expensive (average of $652). 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 $979, American Airlines can have you in Simpson Bay from Worcester, Massachusetts in 22h 02m. 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 $459). Flying from Worcester, Massachusetts to Simpson Bay in March is currently the most expensive (average of $652). 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.