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

American Airlines, JetBlue, and Delta 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 58% of people opting to fly with this airline when traveling to Simpson Bay. Keep in mind that there are 6 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 3 as of August 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.

$293 Cheap Flights from Portland to Simpson Bay in 2025

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Find the cheapest flights from Portland, Maine to Simpson Bay

Round-trip

One-way

Cheap round-trip flights

5:10 pm - 1:19 pmPWM-SXM

20h 09m2 stops

4:24 pm - 1:52 pmSXM-PWM

21h 28m2 stops

$567American Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 11

5:17 pm - 12:10 pmPWM-SXM

17h 53m2 stops

4:15 pm - 12:05 pmSXM-PWM

20h 50m2 stops

$616American Airlines

Find Deal

Fri, Jan 2 - Sun, Jan 11

6:33 pm - 1:50 pmPWM-SXM

19h 17m2 stops

3:20 pm - 2:01 pmSXM-PWM

22h 41m2 stops

$657Delta

Find Deal

Sat, Sep 27 - Wed, Oct 1

7:43 am - 1:55 pmPWM-SXM

29h 12m1 stop

4:15 pm - 12:05 pmSXM-PWM

20h 50m2 stops

$665American Airlines

Find Deal

Wed, Jan 7 - Sun, Jan 11

7:00 am - 1:50 pmPWM-SXM

30h 50m2 stops

3:20 pm - 12:11 amSXM-PWM

8h 51m1 stop

$789Delta

Find Deal

Sat, Sep 27 - Wed, Oct 1

2:17 pm - 1:15 pmPWM-SXM

22h 58m1 stop

3:31 pm - 1:22 pmSXM-PWM

21h 51m1 stop

$841JetBlue

Find Deal

Sat, Oct 4 - Sat, Oct 11

6:18 pm - 2:00 pmPWM-SXM

43h 42m3 stops

3:05 pm - 2:30 pmSXM-PWM

23h 25m3 stops

$846

Find Deal

Sat, Oct 4 - Sat, Oct 11

7:22 pm - 1:51 pmPWM-SXM

17h 29m2 stops

4:55 pm - 11:17 pmSXM-PWM

31h 22m3 stops

$849United Airlines

Find Deal

Wed, Jan 7 - Sun, Jan 11

6:00 am - 1:51 pmPWM-SXM

6h 51m1 stop

4:55 pm - 10:44 amSXM-PWM

18h 49m1 stop

$857United Airlines

Find Deal

Wed, Jan 7 - Sun, Jan 11

11:16 am - 1:14 pmPWM-SXM

25h 58m2 stops

3:05 pm - 2:30 pmSXM-PWM

23h 25m3 stops

$1,153

Find Deal

Sat, Oct 4 - Sat, Oct 11

American Airlines flights from Portland, Maine to Simpson Bay

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

American Airlines

Oct 4

PWM5:10 pmPortland

20h 09m

2 stops

SXM1:19 pmSimpson Bay Princess Juliana

Oct 11

SXM4:24 pmSimpson Bay Princess Juliana

21h 28m

2 stops

PWM1:52 pmPortland

$567

Find similar

American Airlines

Jan 2

PWM5:17 pmPortland

17h 53m

2 stops

SXM12:10 pmSimpson Bay Princess Juliana

Jan 11

SXM4:15 pmSimpson Bay Princess Juliana

20h 50m

2 stops

PWM12:05 pmPortland

$616

Find similar

American Airlines

Jan 7

PWM7:43 amPortland

29h 12m

1 stop

SXM1:55 pmSimpson Bay Princess Juliana

Jan 11

SXM4:15 pmSimpson Bay Princess Juliana

20h 50m

2 stops

PWM12:05 pmPortland

$665

Find similar

United Airlines flights from Portland, Maine to Simpson Bay

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

United Airlines

Jan 7

PWM7:22 pmPortland

17h 29m

2 stops

SXM1:51 pmSimpson Bay Princess Juliana

Jan 11

SXM4:55 pmSimpson Bay Princess Juliana

31h 22m

3 stops

PWM11:17 pmPortland

$849

Find similar

United Airlines

Jan 7

PWM6:00 amPortland

6h 51m

1 stop

SXM1:51 pmSimpson Bay Princess Juliana

Jan 11

SXM4:55 pmSimpson Bay Princess Juliana

18h 49m

1 stop

PWM10:44 amPortland

$857

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

Sat 10/4

5:10 pm-1:19 pm

2 stops20h 09m

Simpson Bay Princess Juliana

Sat 10/11

4:24 pm-1:52 pm

2 stops21h 28m

$567

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 1/2

5:17 pm-12:10 pm

2 stops17h 53m

Simpson Bay Princess Juliana

Sun 1/11

4:15 pm-12:05 pm

2 stops20h 50m

$616

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 9/27

6:33 pm-1:50 pm

2 stops19h 17m

Simpson Bay Princess Juliana

Wed 10/1

3:20 pm-2:01 pm

2 stops22h 41m

$657

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

7:43 am-1:55 pm

1 stop29h 12m

Simpson Bay Princess Juliana

Sun 1/11

4:15 pm-12:05 pm

2 stops20h 50m

$665

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 9/27

7:00 am-1:50 pm

2 stops30h 50m

Simpson Bay Princess Juliana

Wed 10/1

3:20 pm-12:11 am

1 stop8h 51m

$789

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 10/4

2:17 pm-1:15 pm

1 stop22h 58m

Simpson Bay Princess Juliana

Sat 10/11

3:31 pm-1:22 pm

1 stop21h 51m

$841

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 10/4

6:18 pm-2:00 pm

3 stops43h 42m

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-2:30 pm

3 stops23h 25m

$846

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

7:22 pm-1:51 pm

2 stops17h 29m

Simpson Bay Princess Juliana

Sun 1/11

4:55 pm-11:17 pm

3 stops31h 22m

$849

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 1/7

6:00 am-1:51 pm

1 stop6h 51m

Simpson Bay Princess Juliana

Sun 1/11

4:55 pm-10:44 am

1 stop18h 49m

$857

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 10/4

11:16 am-1:14 pm

2 stops25h 58m

Simpson Bay Princess Juliana

Sat 10/11

3:05 pm-2:30 pm

3 stops23h 25m

$1,153

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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

Prices

Airlines

What is the cheapest month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Portland, Maine to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $416. If you aren’t able to travel to Simpson Bay during the month of September, then flying in April is also cheap. Prices for this month can be found on momondo for an average of $624.

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

Best Price Found	$293
Fastest flight time	6h 25m
Direct flights	None
Airports in Simpson Bay	1 airport

The best one-way flight to Simpson Bay from Portland, Maine in the past 72 hours is $293. The best round-trip flight deal from Portland, Maine to Simpson Bay found on momondo in the last 72 hours is $567.

The fastest flight from Portland, Maine to Simpson Bay takes 6h 25m

There are no direct flights from Portland, Maine to Simpson Bay. Popular non-direct route for this connection is Portland Airport - Simpson Bay Princess Juliana Airport.

There is 1 airport near Simpson Bay: Simpson Bay Princess Juliana (SXM)

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 25m, 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 3 as of August 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 (44% of total bookings). The next most popular airlines are United Airlines (34%) and American Airlines (22%).

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 8.0 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $540	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
American Airlines	PriceFrom $566	Free Cancellation	Rating 7.2 10,000 reviews	Search American 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.

An easier way to manage your Simpson Bay trip

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Cheap flights from Portland, Maine to Simpson Bay from $293

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 10/2. 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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Big names and deals

Filter for what you want

Filter for what you want

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Find the cheapest flights from Portland, Maine to Simpson Bay

Cheap round-trip flights

Cheap one-way flights

American Airlines flights from Portland, Maine to Simpson Bay

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

United Airlines flights from Portland, Maine to Simpson Bay

Our best United Airlines 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 month to fly to Simpson Bay?

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

American Airlines, JetBlue, and Delta are the most popular carriers operating 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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Simpson Bay

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