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

Prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport refresh daily.

How many operators does momondo search for flights from Portland Airport to Simpson Bay Princess Juliana Airport?

The number of operators available for flights from Portland Airport to Simpson Bay Princess Juliana Airport is 2 as of October 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Simpson Bay Princess Juliana Airport.

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

The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$149 Cheap Flights from Portland, Maine to Simpson Bay in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Simpson Bay

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:47 pm - 4:31 pmPWM Portland-SXM Simpson Bay Princess Juliana

20h 44m2 stops Philadelphia Miami

3:29 pm - 12:17 pmSXM Simpson Bay Princess Juliana-PWM Portland

21h 48m2 stops Charlotte Douglas Philadelphia

$380American Airlines

Mon, Dec 14 - Fri, Dec 18

6:47 pm - 4:26 pmPWM Portland-SXM Simpson Bay Princess Juliana

20h 39m2 stops Philadelphia Miami

3:27 pm - 11:58 amSXM Simpson Bay Princess Juliana-PWM Portland

21h 31m2 stops Miami Chicago O'Hare Intl

$380American Airlines

Tue, Dec 1 - Tue, Dec 15

6:47 pm - 4:26 pmPWM Portland-SXM Simpson Bay Princess Juliana

20h 39m2 stops Philadelphia Miami

5:33 pm - 11:58 amSXM Simpson Bay Princess Juliana-PWM Portland

19h 25m2 stops Miami Chicago O'Hare Intl

$380American Airlines

Tue, Dec 1 - Tue, Dec 15

6:47 pm - 1:26 pmPWM Portland-SXM Simpson Bay Princess Juliana

17h 39m2 stops Philadelphia Charlotte Douglas

5:33 pm - 11:53 amSXM Simpson Bay Princess Juliana-PWM Portland

19h 20m2 stops Miami Chicago O'Hare Intl

$380American Airlines

Tue, Dec 1 - Tue, Dec 15

7:55 pm - 1:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

16h 55m1 stop Newark

2:52 pm - 9:30 pmSXM Simpson Bay Princess Juliana-PWM Portland

7h 38m1 stop Newark

$508United Airlines

Tue, Dec 1 - Sat, Dec 12

5:50 am - 12:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 00m1 stop Newark

1:52 pm - 11:21 pmSXM Simpson Bay Princess Juliana-PWM Portland

9h 29m1 stop Newark

$525United Airlines

Tue, Oct 27 - Fri, Oct 30

5:50 am - 12:50 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 00m1 stop Newark

1:52 pm - 2:16 pmSXM Simpson Bay Princess Juliana-PWM Portland

24h 24m2 stops Newark Chicago O'Hare Intl

$530United Airlines

Tue, Oct 27 - Fri, Oct 30

5:25 am - 1:55 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 30m1 stop Baltimore/Washington

4:15 pm - 11:45 pmSXM Simpson Bay Princess Juliana-PWM Portland

8h 30m1 stop Baltimore/Washington

$655Southwest

Sun, Feb 28 - Sun, Mar 7

5:25 am - 1:55 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 30m1 stop Baltimore/Washington

2:55 pm - 8:10 amSXM Simpson Bay Princess Juliana-PWM Portland

18h 15m2 stops Orlando Baltimore/Washington

$660Southwest

Sun, Feb 28 - Sun, Mar 7

6:00 am - 1:25 pmPWM Portland-SXM Simpson Bay Princess Juliana

7h 25m1 stop New York John F Kennedy Intl

2:50 pm - 11:43 pmSXM Simpson Bay Princess Juliana-PWM Portland

8h 53m1 stop New York John F Kennedy Intl

$1,873JetBlue

Thu, Oct 22 - Thu, Oct 29

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United Airlines flights from Portland, Maine to Simpson Bay

Our best United Airlines deals on Portland, Maine to Simpson Bay flight tickets

United Airlines

Dec 1

PWM7:55 pmPortland

16h 55m

1 stop

SXM1:50 pmSimpson Bay Princess Juliana

Dec 12

SXM2:52 pmSimpson Bay Princess Juliana

7h 38m

1 stop

PWM9:30 pmPortland

$508

United Airlines

Oct 27

PWM5:50 amPortland

7h 00m

1 stop

SXM12:50 pmSimpson Bay Princess Juliana

Oct 30

SXM1:52 pmSimpson Bay Princess Juliana

9h 29m

1 stop

PWM11:21 pmPortland

$525

United Airlines

Oct 27

PWM5:50 amPortland

7h 00m

1 stop

SXM12:50 pmSimpson Bay Princess Juliana

Oct 30

SXM1:52 pmSimpson Bay Princess Juliana

24h 24m

2 stops

PWM2:16 pmPortland

$530

Southwest flights from Portland, Maine to Simpson Bay

Our best Southwest deals on Portland, Maine to Simpson Bay flight tickets

Southwest

Feb 28

PWM5:25 amPortland

7h 30m

1 stop

SXM1:55 pmSimpson Bay Princess Juliana

Mar 7

SXM4:15 pmSimpson Bay Princess Juliana

8h 30m

1 stop

PWM11:45 pmPortland

$655

Southwest

Feb 28

PWM5:25 amPortland

7h 30m

1 stop

SXM1:55 pmSimpson Bay Princess Juliana

Mar 7

SXM2:55 pmSimpson Bay Princess Juliana

18h 15m

2 stops

PWM8:10 amPortland

$660

momondo Fare Finder

Use the filters below to find and compare flights from Portland, Maine to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Mon 12/14

6:47 pm-4:31 pm

2 stops20h 44m

Simpson Bay Princess Juliana

Fri 12/18

3:29 pm-12:17 pm

2 stops21h 48m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 12/1

6:47 pm-4:26 pm

2 stops20h 39m

Simpson Bay Princess Juliana

Tue 12/15

3:27 pm-11:58 am

2 stops21h 31m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 12/1

6:47 pm-4:26 pm

2 stops20h 39m

Simpson Bay Princess Juliana

Tue 12/15

5:33 pm-11:58 am

2 stops19h 25m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 12/1

6:47 pm-1:26 pm

2 stops17h 39m

Simpson Bay Princess Juliana

Tue 12/15

5:33 pm-11:53 am

2 stops19h 20m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 12/1

7:55 pm-1:50 pm

1 stop16h 55m

Simpson Bay Princess Juliana

Sat 12/12

2:52 pm-9:30 pm

1 stop7h 38m

$508

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 10/27

5:50 am-12:50 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 10/30

1:52 pm-11:21 pm

1 stop9h 29m

$525

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 10/27

5:50 am-12:50 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Fri 10/30

1:52 pm-2:16 pm

2 stops24h 24m

$530

Quickest round-trip

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Sun 2/28

5:25 am-1:55 pm

1 stop7h 30m

Simpson Bay Princess Juliana

Sun 3/7

4:15 pm-11:45 pm

1 stop8h 30m

$655

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Sun 2/28

5:25 am-1:55 pm

1 stop7h 30m

Simpson Bay Princess Juliana

Sun 3/7

2:55 pm-8:10 am

2 stops18h 15m

$660

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Thu 10/22

6:00 am-1:25 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 10/29

2:50 pm-11:43 pm

1 stop8h 53m

$1,873

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first

How to get the cheapest flight ticket from Portland, Maine 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 airline that flies from Portland to Simpson Bay Princess Juliana?

American Airlines and United Airlines are the most popular carriers operating from Portland to Simpson Bay Princess Juliana

What airlines fly to Simpson Bay?

JetBlue, American Airlines and United Airlines are the top three most popular airlines that fly to Simpson Bay from Portland, Maine according to our data. JetBlue is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 5 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

When to book flights from Portland, Maine to Simpson Bay

Are you open to changing your travel dates? Check out the ideal times to fly from Portland, Maine to Simpson Bay according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Portland, Maine to Simpson Bay (PWM to SXM) flight deals and tips

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

Best Price Found	$149
Fastest flight time	6h 50m
Direct flights	None

The best one-way flight to Simpson Bay from Portland, Maine in the past 72 hours is $149. The best round-trip flight deal from Portland, Maine to Simpson Bay found on momondo in the last 72 hours is $380.

The fastest flight from Portland, Maine to Simpson Bay takes 6h 50m

There are no direct flights from Portland, Maine to Simpson Bay. There are no popular flight routes from Portland, Maine to Simpson Bay.

Search flight deals

Frequently asked questions about flying from Portland, Maine to Simpson Bay

How far is Portland to Simpson Bay Princess Juliana by plane?
A flight from Portland to Simpson Bay Princess Juliana will travel around 1817.3 mi. Flights usually cover this in 6h 50m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport?
Prices for flights from Portland Airport to Simpson Bay Princess Juliana Airport refresh daily.
How many operators does momondo search for flights from Portland Airport to Simpson Bay Princess Juliana Airport?
The number of operators available for flights from Portland Airport to Simpson Bay Princess Juliana Airport is 2 as of October 2026.
How old do you have to be to fly from Portland Airport to Simpson Bay Princess Juliana Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Simpson Bay Princess Juliana Airport.
What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?
The travel and health documents you'll need for your trip to Simpson Bay Princess Juliana Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Simpson Bay Princess Juliana Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular airline from Portland, Maine to Simpson Bay?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Portland, Maine to Simpson Bay is American Airlines (60% of total bookings). The next most popular airline is United Airlines (40%).

Best airlines flying from Portland, Maine to Simpson Bay

Compare and see reviews for airlines that fly from Portland, Maine to Simpson Bay with momondo

Airline	Rating	Free Cancellation	Price
United Airlines	PriceFrom $305	Free Cancellation	Rating 7.4 10,270 reviews		Search United Airlines flights
American Airlines	PriceFrom $402	Free Cancellation	Rating 7.0 12,101 reviews		Search American Airlines flights

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

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

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

Yes. All flights to Simpson Bay from Portland on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo provides multiple filters to help you find the best flight to Simpson Bay from Portland. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

If you are not ready to book a flight from Portland 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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Cheap flights from Portland, Maine to Simpson Bay from $149

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Portland, Maine to Simpson Bay departing on 12/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Portland, Maine to Simpson Bay

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Southwest flights from Portland, Maine to Simpson Bay

Our best Southwest deals on Portland, Maine to Simpson Bay flight tickets

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Use the filters below to find and compare flights from Portland, Maine to Simpson Bay that are best for you.

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How to get the cheapest flight ticket from Portland, Maine to Simpson Bay

What is the cheapest airline that flies from Portland to Simpson Bay Princess Juliana?

What airlines fly to Simpson Bay?

When to book flights from Portland, Maine to Simpson Bay

Cheap Portland, Maine to Simpson Bay (PWM to SXM) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Portland, Maine to Simpson Bay

Best airlines flying from Portland, Maine to Simpson Bay

Compare and see reviews for airlines that fly from Portland, Maine to Simpson Bay with momondo

Traveling to a place near Simpson Bay?

Why use momondo?

An easier way to manage your Simpson Bay trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Fly your favorite airline to Simpson Bay

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Simpson Bay

List of cabin classes available on flights landing in Simpson Bay. Availability may vary depending on flight origin and airline.

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