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 57% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 7 different airlines that fly to Simpson Bay on a routine basis, so you have a few additional options to choose from.

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 November 2025.

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.

$367 Cheap Flights from Portland to Simpson Bay in 2025/26

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12:46 pm - 1:45 pmPWM-SXM

23h 59m2 stops

5:33 pm - 12:06 pmSXM-PWM

19h 33m2 stops

$367American Airlines

Find Deal

Wed, Jan 7 - Sun, Jan 11

3:56 pm - 1:52 pmPWM-SXM

20h 56m1 stop

3:50 pm - 10:54 pmSXM-PWM

8h 04m1 stop

$369American Airlines

Find Deal

Wed, Jan 7 - Sun, Jan 11

5:30 am - 1:53 pmPWM-SXM

8h 23m1 stop

3:45 pm - 11:49 pmSXM-PWM

8h 04m1 stop

$403Delta

Find Deal

Mon, Mar 30 - Wed, Apr 1

11:25 am - 1:53 pmPWM-SXM

26h 28m2 stops

3:45 pm - 11:49 pmSXM-PWM

8h 04m1 stop

$408Delta

Find Deal

Mon, Mar 30 - Wed, Apr 1

5:20 pm - 3:10 pmPWM-SXM

21h 50m2 stops

4:15 pm - 10:30 pmSXM-PWM

30h 15m2 stops

$500American Airlines

Find Deal

Mon, Mar 30 - Wed, Apr 1

6:00 am - 1:50 pmPWM-SXM

6h 50m1 stop

2:52 pm - 11:22 pmSXM-PWM

9h 30m1 stop

$556United Airlines

Find Deal

Tue, Dec 16 - Tue, Dec 23

6:00 am - 1:50 pmPWM-SXM

6h 50m1 stop

4:55 pm - 9:29 pmSXM-PWM

53h 34m2 stops

$578United Airlines

Find Deal

Tue, Dec 16 - Tue, Dec 23

6:00 am - 1:50 pmPWM-SXM

54h 50m3 stops

2:52 pm - 11:22 pmSXM-PWM

9h 30m1 stop

$684United Airlines

Find Deal

Tue, Dec 16 - Tue, Dec 23

6:00 am - 2:55 pmPWM-SXM

7h 55m1 stop

4:30 pm - 11:59 pmSXM-PWM

8h 29m1 stop

$1,582Delta

Find Deal

Tue, Nov 25 - Sat, Nov 29

5:31 am - 2:56 pmPWM-SXM

8h 25m1 stop

1:45 pm - 12:20 amSXM-PWM

11h 35m2 stops

$2,425Delta

Find Deal

Thu, Feb 12 - Fri, Feb 20

American Airlines flights from Portland, Maine to Simpson Bay

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

American Airlines

Jan 7

PWM12:46 pmPortland

23h 59m

2 stops

SXM1:45 pmSimpson Bay Princess Juliana

Jan 11

SXM5:33 pmSimpson Bay Princess Juliana

19h 33m

2 stops

PWM12:06 pmPortland

$367

Find similar

American Airlines

Jan 7

PWM3:56 pmPortland

20h 56m

1 stop

SXM1:52 pmSimpson Bay Princess Juliana

Jan 11

SXM3:50 pmSimpson Bay Princess Juliana

8h 04m

1 stop

PWM10:54 pmPortland

$369

Find similar

American Airlines

Mar 30

PWM5:20 pmPortland

21h 50m

2 stops

SXM3:10 pmSimpson Bay Princess Juliana

Apr 1

SXM4:15 pmSimpson Bay Princess Juliana

30h 15m

2 stops

PWM10:30 pmPortland

$500

Find similar

Delta flights from Portland, Maine to Simpson Bay

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

Delta

Mar 30

PWM5:30 amPortland

8h 23m

1 stop

SXM1:53 pmSimpson Bay Princess Juliana

Apr 1

SXM3:45 pmSimpson Bay Princess Juliana

8h 04m

1 stop

PWM11:49 pmPortland

$403

Find similar

Delta

Mar 30

PWM11:25 amPortland

26h 28m

2 stops

SXM1:53 pmSimpson Bay Princess Juliana

Apr 1

SXM3:45 pmSimpson Bay Princess Juliana

8h 04m

1 stop

PWM11:49 pmPortland

$408

Find similar

Delta

Nov 25

PWM6:00 amPortland

7h 55m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Nov 29

SXM4:30 pmSimpson Bay Princess Juliana

8h 29m

1 stop

PWM11:59 pmPortland

$1,582

Find similar

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

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

12:46 pm-1:45 pm

2 stops23h 59m

Simpson Bay Princess Juliana

Sun 1/11

5:33 pm-12:06 pm

2 stops19h 33m

$367

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

3:56 pm-1:52 pm

1 stop20h 56m

Simpson Bay Princess Juliana

Sun 1/11

3:50 pm-10:54 pm

1 stop8h 04m

$369

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:30 am-1:53 pm

1 stop8h 23m

Simpson Bay Princess Juliana

Wed 4/1

3:45 pm-11:49 pm

1 stop8h 04m

$403

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

11:25 am-1:53 pm

2 stops26h 28m

Simpson Bay Princess Juliana

Wed 4/1

3:45 pm-11:49 pm

1 stop8h 04m

$408

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:20 pm-3:10 pm

2 stops21h 50m

Simpson Bay Princess Juliana

Wed 4/1

4:15 pm-10:30 pm

2 stops30h 15m

$500

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 12/16

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 12/23

2:52 pm-11:22 pm

1 stop9h 30m

$556

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 12/16

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 12/23

4:55 pm-9:29 pm

2 stops53h 34m

$578

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 12/16

6:00 am-1:50 pm

3 stops54h 50m

Simpson Bay Princess Juliana

Tue 12/23

2:52 pm-11:22 pm

1 stop9h 30m

$684

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 11/25

6:00 am-2:55 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 11/29

4:30 pm-11:59 pm

1 stop8h 29m

$1,582

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 2/12

5:31 am-2:56 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Fri 2/20

1:45 pm-12:20 am

2 stops11h 35m

$2,425

Flights are sorted by cheapest round-trip flights first.

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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

Prices

Airlines

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

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $641. Flights from Portland, Maine to Simpson Bay on a Sunday will generally be more expensive and average around $1,165. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

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

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Portland, Maine to Simpson Bay in the afternoon for as low as $661. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $807.

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

Direct flights	None

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

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 November 2025.
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 Delta (58% of total bookings). The next most popular airline is United Airlines (42%).

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
Delta	PriceFrom $286	Free Cancellation	Rating 7.9 7,997 reviews		Search Delta flights
United Airlines	PriceFrom $540	Free Cancellation	Rating 7.4 8,994 reviews		Search United Airlines flights

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Why use momondo?

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 $367

This is the cheapest round-trip 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 1/7. 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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Filter for what you want

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Cheap round-trip flights

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American Airlines flights from Portland, Maine to Simpson Bay

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

Delta flights from Portland, Maine to Simpson Bay

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

momondo Fare Finder

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

See travel insights to Simpson Bay from

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 day to depart on your flight to Simpson Bay?

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

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

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

Direct flights

How far is Portland to Simpson Bay Princess Juliana by plane?

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

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

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

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

What is the most popular airline 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?

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

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

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

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

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