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Cheap flights from Worcester, Massachusetts to Simpson Bay from $394

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Worcester, Massachusetts to Simpson Bay departing on 9/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Worcester, Massachusetts to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:16 pm - 1:23 pmORH  Worcester-SXM Simpson Bay Princess Juliana
20h 07m2 stops Philadelphia Miami
American Airlines Logo
2:23 pm - 4:49 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
26h 26m2 stops Miami Philadelphia
$394American Airlines
Fri, Sep 18 - Fri, Sep 25
American Airlines Logo
5:16 pm - 1:23 pmORH  Worcester-SXM Simpson Bay Princess Juliana
20h 07m2 stops Philadelphia Miami
American Airlines Logo
2:23 pm - 4:49 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
26h 26m2 stops Miami Philadelphia
$529American Airlines
Sun, Sep 20 - Sun, Sep 27
American Airlines Logo
5:16 pm - 1:23 pmORH  Worcester-SXM Simpson Bay Princess Juliana
20h 07m2 stops Philadelphia Miami
American Airlines Logo
2:23 pm - 4:49 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
26h 26m2 stops Miami Philadelphia
$529American Airlines
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
1:45 pm - 2:10 pmORH  Worcester-SXM Simpson Bay Princess Juliana
23h 25m1 stop Philadelphia
American Airlines Logo
1:39 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
24h 38m2 stops Miami Philadelphia
$708American Airlines
Sun, Dec 20 - Mon, Dec 28
American Airlines Logo
1:45 pm - 2:10 pmORH  Worcester-SXM Simpson Bay Princess Juliana
23h 25m1 stop Philadelphia
American Airlines Logo
3:10 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
23h 07m1 stop Philadelphia
$710American Airlines
Sun, Dec 20 - Sat, Dec 26
American Airlines Logo
1:45 pm - 1:59 pmORH  Worcester-SXM Simpson Bay Princess Juliana
23h 14m2 stops Philadelphia Charlotte Douglas
American Airlines Logo
1:39 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
24h 38m2 stops Miami Philadelphia
$742American Airlines
Sun, Dec 20 - Mon, Dec 28
American Airlines Logo
1:45 pm - 1:59 pmORH  Worcester-SXM Simpson Bay Princess Juliana
23h 14m2 stops Philadelphia Charlotte Douglas
American Airlines Logo
3:10 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
23h 07m1 stop Philadelphia
$744American Airlines
Sun, Dec 20 - Sat, Dec 26
American Airlines Logo
1:45 pm - 2:10 pmORH  Worcester-SXM Simpson Bay Princess Juliana
23h 25m1 stop Philadelphia
American Airlines Logo
3:28 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
22h 49m2 stops Miami Philadelphia
$758American Airlines
Sun, Dec 20 - Tue, Dec 29
American Airlines Logo
1:45 pm - 4:33 pmORH  Worcester-SXM Simpson Bay Princess Juliana
49h 48m2 stops Philadelphia Miami
American Airlines Logo
1:39 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
24h 38m2 stops Miami Philadelphia
$768American Airlines
Sat, Dec 19 - Mon, Dec 28
American Airlines Logo
1:45 pm - 4:33 pmORH  Worcester-SXM Simpson Bay Princess Juliana
49h 48m2 stops Philadelphia Miami
American Airlines Logo
3:10 pm - 1:17 pmSXM  Simpson Bay Princess Juliana-ORH Worcester
23h 07m1 stop Philadelphia
$771American Airlines
Sat, Dec 19 - Sat, Dec 26

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American Airlines flights from Worcester, Massachusetts to Simpson Bay

Our best American Airlines deals on Worcester, Massachusetts to Simpson Bay flight tickets
American Airlines
Sep 18
ORH5:16 pmWorcester
20h 07m
2 stops
SXM1:23 pmSimpson Bay Princess Juliana
Sep 25
SXM2:23 pmSimpson Bay Princess Juliana
26h 26m
2 stops
ORH4:49 pmWorcester
$394
American Airlines
Sep 20
ORH5:16 pmWorcester
20h 07m
2 stops
SXM1:23 pmSimpson Bay Princess Juliana
Sep 27
SXM2:23 pmSimpson Bay Princess Juliana
26h 26m
2 stops
ORH4:49 pmWorcester
$529
American Airlines
Dec 20
ORH1:45 pmWorcester
23h 25m
1 stop
SXM2:10 pmSimpson Bay Princess Juliana
Dec 28
SXM1:39 pmSimpson Bay Princess Juliana
24h 38m
2 stops
ORH1:17 pmWorcester
$708

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts 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, momondo users made 832,500 searches. Data last updated August 9, 2026.
Use the filters below to find and compare flights from Worcester, Massachusetts to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Fri 9/18

5:16 pm-1:23 pm

2 stops20h 07m

Simpson Bay Princess Juliana

Fri 9/25

2:23 pm-4:49 pm

2 stops26h 26m

$394

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 9/20

5:16 pm-1:23 pm

2 stops20h 07m

Simpson Bay Princess Juliana

Sun 9/27

2:23 pm-4:49 pm

2 stops26h 26m

$529

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Wed 9/23

5:16 pm-1:23 pm

2 stops20h 07m

Simpson Bay Princess Juliana

Wed 9/30

2:23 pm-4:49 pm

2 stops26h 26m

$529

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 12/20

1:45 pm-2:10 pm

1 stop23h 25m

Simpson Bay Princess Juliana

Mon 12/28

1:39 pm-1:17 pm

2 stops24h 38m

$708

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 12/20

1:45 pm-2:10 pm

1 stop23h 25m

Simpson Bay Princess Juliana

Sat 12/26

3:10 pm-1:17 pm

1 stop23h 07m

$710

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 12/20

1:45 pm-1:59 pm

2 stops23h 14m

Simpson Bay Princess Juliana

Mon 12/28

1:39 pm-1:17 pm

2 stops24h 38m

$742

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 12/20

1:45 pm-1:59 pm

2 stops23h 14m

Simpson Bay Princess Juliana

Sat 12/26

3:10 pm-1:17 pm

1 stop23h 07m

$744
Quickest round-trip

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sun 12/20

1:45 pm-2:10 pm

1 stop23h 25m

Simpson Bay Princess Juliana

Tue 12/29

3:28 pm-1:17 pm

2 stops22h 49m

$758

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sat 12/19

1:45 pm-4:33 pm

2 stops49h 48m

Simpson Bay Princess Juliana

Mon 12/28

1:39 pm-1:17 pm

2 stops24h 38m

$768

WorcesterSimpson Bay

ORH Worcester - SXM Simpson Bay Princess Juliana

ORHSXM

Worcester

Sat 12/19

1:45 pm-4:33 pm

2 stops49h 48m

Simpson Bay Princess Juliana

Sat 12/26

3:10 pm-1:17 pm

1 stop23h 07m

$771

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Worcester, Massachusetts to Simpson Bay

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Simpson Bay?

Our data shows that Wednesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $408. Flights from Worcester, Massachusetts to Simpson Bay on a Saturday will generally be more expensive and average around $624. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

When to book flights from Worcester, Massachusetts to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Worcester, Massachusetts to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Worcester, Massachusetts to Simpson Bay (ORH to SXM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Worcester, Massachusetts to Simpson Bay

Fastest flight time

19h 37m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Simpson Bay takes 19h 37m
There are no direct flights from Worcester, Massachusetts to Simpson Bay. There are no popular flight routes from Worcester, Massachusetts to Simpson Bay.
Search flight deals

Frequently asked questions about flying from Worcester, Massachusetts to Simpson Bay

  • How far is Worcester to Simpson Bay Princess Juliana by plane?

    The straight-line distance from Worcester to Simpson Bay Princess Juliana is 1748.8 mi. Typically, this will take 19h 37m by plane in normal conditions.

  • When did momondo last update prices for flights from Worcester Airport to Simpson Bay Princess Juliana Airport?

    Prices for flights from Worcester Airport to Simpson Bay Princess Juliana Airport are updated daily.

  • How old do you have to be to fly from Worcester Airport to Simpson Bay Princess Juliana Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Worcester Airport to Simpson Bay Princess Juliana Airport.

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The required travel and health documents for your Simpson Bay Princess Juliana Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Worcester to Simpson Bay?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Worcester to Simpson Bay. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Worcester to Simpson Bay with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Worcester to Simpson Bay flights to just show those with flexible booking policies.

How can momondo help me find flights from Worcester to Simpson Bay?

Once all potential Worcester to Simpson Bay flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Worcester to Simpson Bay right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Worcester to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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