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Cheap flights from Portland, Maine to Simpson Bay from $173

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 7/18. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Portland, Maine to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:22 pm - 1:55 pm
PWM
-
SXM
17h 33m
2 stops
United Airlines Logo
5:00 pm - 8:19 am
SXM
-
PWM
16h 19m
2 stops
$372United Airlines
Sat, Nov 14 - Sat, Nov 21
American Airlines Logo
6:46 pm - 3:39 pm
PWM
-
SXM
20h 53m
2 stops
American Airlines Logo
4:39 pm - 2:21 pm
SXM
-
PWM
21h 42m
2 stops
$377American Airlines
Sun, Aug 23 - Sun, Aug 30
American Airlines Logo
6:46 pm - 1:22 pm
PWM
-
SXM
18h 36m
2 stops
American Airlines Logo
4:39 pm - 2:21 pm
SXM
-
PWM
21h 42m
2 stops
$382American Airlines
Sun, Aug 23 - Fri, Aug 28
American Airlines Logo
6:46 pm - 1:22 pm
PWM
-
SXM
18h 36m
2 stops
American Airlines Logo
2:42 pm - 5:41 pm
SXM
-
PWM
26h 59m
1 stop
$389American Airlines
Sun, Aug 23 - Fri, Aug 28
American Airlines Logo
4:31 pm - 1:22 pm
PWM
-
SXM
20h 51m
2 stops
American Airlines Logo
2:22 pm - 1:12 pm
SXM
-
PWM
22h 50m
2 stops
$391American Airlines
Sun, Sep 13 - Sun, Sep 20
American Airlines Logo
6:59 pm - 12:34 pm
PWM
-
SXM
17h 35m
1 stop
American Airlines Logo
2:46 pm - 10:33 pm
SXM
-
PWM
7h 47m
1 stop
$393American Airlines
Fri, Jul 3 - Fri, Jul 10
American Airlines Logo
6:59 pm - 12:34 pm
PWM
-
SXM
17h 35m
1 stop
American Airlines Logo
1:34 pm - 9:22 am
SXM
-
PWM
19h 48m
2 stops
$398American Airlines
Fri, Jul 3 - Fri, Jul 10
American Airlines Logo
6:59 pm - 12:34 pm
PWM
-
SXM
17h 35m
1 stop
American Airlines Logo
2:46 pm - 10:33 pm
SXM
-
PWM
7h 47m
1 stop
$403American Airlines
Fri, Jul 3 - Fri, Jul 10
American Airlines Logo
6:59 pm - 3:44 pm
PWM
-
SXM
20h 45m
2 stops
American Airlines Logo
1:34 pm - 9:22 am
SXM
-
PWM
19h 48m
2 stops
$408American Airlines
Fri, Jul 3 - Fri, Jul 10
United Airlines Logo
7:16 pm - 2:43 pm
PWM
-
SXM
19h 27m
2 stops
United Airlines Logo
3:50 pm - 11:51 pm
SXM
-
PWM
8h 01m
1 stop
$420United Airlines
Mon, Aug 3 - Thu, Aug 6

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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
American Airlines
Aug 23
PWM6:46 pmPortland
20h 53m
2 stops
SXM3:39 pmSimpson Bay Princess Juliana
Aug 30
SXM4:39 pmSimpson Bay Princess Juliana
21h 42m
2 stops
PWM2:21 pmPortland
$377
American Airlines
Aug 23
PWM6:46 pmPortland
18h 36m
2 stops
SXM1:22 pmSimpson Bay Princess Juliana
Aug 28
SXM4:39 pmSimpson Bay Princess Juliana
21h 42m
2 stops
PWM2:21 pmPortland
$382
American Airlines
Aug 23
PWM6:46 pmPortland
18h 36m
2 stops
SXM1:22 pmSimpson Bay Princess Juliana
Aug 28
SXM2:42 pmSimpson Bay Princess Juliana
26h 59m
1 stop
PWM5:41 pmPortland
$389

JetBlue flights from Portland, Maine to Simpson Bay

Our best JetBlue deals on Portland, Maine to Simpson Bay flight tickets
JetBlue
Oct 5
PWM6:00 amPortland
7h 25m
1 stop
SXM1:25 pmSimpson Bay Princess Juliana
Oct 11
SXM2:45 pmSimpson Bay Princess Juliana
9h 07m
1 stop
PWM11:52 pmPortland
$545
JetBlue
Sep 18
PWM6:00 amPortland
7h 25m
1 stop
SXM1:25 pmSimpson Bay Princess Juliana
Sep 25
SXM2:45 pmSimpson Bay Princess Juliana
9h 07m
1 stop
PWM11:52 pmPortland
$546
JetBlue
Oct 5
PWM6:00 amPortland
7h 25m
1 stop
SXM1:25 pmSimpson Bay Princess Juliana
Oct 13
SXM2:45 pmSimpson Bay Princess Juliana
9h 07m
1 stop
PWM11:52 pmPortland
$565

momondo Fare Finder

 
Customize your flight search to find flights from Portland, Maine 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 June 19, 2026.
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 - SXM

PWMSXM

Portland

Sat 11/14

7:22 pm-1:55 pm

2 stops17h 33m

Simpson Bay Princess Juliana

Sat 11/21

5:00 pm-8:19 am

2 stops16h 19m

$372

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 8/23

6:46 pm-3:39 pm

2 stops20h 53m

Simpson Bay Princess Juliana

Sun 8/30

4:39 pm-2:21 pm

2 stops21h 42m

$377

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 8/23

6:46 pm-1:22 pm

2 stops18h 36m

Simpson Bay Princess Juliana

Fri 8/28

4:39 pm-2:21 pm

2 stops21h 42m

$382

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 8/23

6:46 pm-1:22 pm

2 stops18h 36m

Simpson Bay Princess Juliana

Fri 8/28

2:42 pm-5:41 pm

1 stop26h 59m

$389

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 9/13

4:31 pm-1:22 pm

2 stops20h 51m

Simpson Bay Princess Juliana

Sun 9/20

2:22 pm-1:12 pm

2 stops22h 50m

$391
Quickest round-trip

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 7/3

6:59 pm-12:34 pm

1 stop17h 35m

Simpson Bay Princess Juliana

Fri 7/10

2:46 pm-10:33 pm

1 stop7h 47m

$393

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 7/3

6:59 pm-12:34 pm

1 stop17h 35m

Simpson Bay Princess Juliana

Fri 7/10

1:34 pm-9:22 am

2 stops19h 48m

$398

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 7/3

6:59 pm-12:34 pm

1 stop17h 35m

Simpson Bay Princess Juliana

Fri 7/10

2:46 pm-10:33 pm

1 stop7h 47m

$403

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 7/3

6:59 pm-3:44 pm

2 stops20h 45m

Simpson Bay Princess Juliana

Fri 7/10

1:34 pm-9:22 am

2 stops19h 48m

$408

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 8/3

7:16 pm-2:43 pm

2 stops19h 27m

Simpson Bay Princess Juliana

Thu 8/6

3:50 pm-11:51 pm

1 stop8h 01m

$420

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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 airline that flies from Portland to Simpson Bay Princess Juliana?

United Airlines and JetBlue 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 63% 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

Fastest flight time

7h 18m

Direct flights

None
The fastest flight from Portland, Maine to Simpson Bay takes 7h 18m
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 7h 18m, 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?

  • 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?

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 AirlinesPriceFrom $305Free CancellationRating
7.4
9,860 reviews
Search United Airlines flights
American AirlinesPriceFrom $583Free CancellationRating
7.1
11,703 reviews
Search American Airlines flights

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 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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