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Cheap flights from Portland, Maine to Simpson Bay from $96

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 3/30. 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
0 bags

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Find the cheapest flights from Portland, Maine to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:40 pm - 3:28 pm
PWM
-
SXM
21h 48m
2 stops
American Airlines Logo
4:28 pm - 12:14 pm
SXM
-
PWM
19h 46m
2 stops
$321American Airlines
Sun, Mar 8 - Sun, Mar 15
American Airlines Logo
5:40 pm - 1:16 pm
PWM
-
SXM
19h 36m
2 stops
American Airlines Logo
12:41 pm - 11:15 am
SXM
-
PWM
22h 34m
2 stops
$328American Airlines
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
5:40 pm - 3:28 pm
PWM
-
SXM
21h 48m
2 stops
American Airlines Logo
12:41 pm - 9:54 am
SXM
-
PWM
21h 13m
2 stops
$335American Airlines
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
6:00 am - 12:45 pm
PWM
-
SXM
6h 45m
1 stop
American Airlines Logo
1:45 pm - 9:44 pm
SXM
-
PWM
7h 59m
1 stop
$354American Airlines
Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
7:35 pm - 3:31 pm
PWM
-
SXM
19h 56m
2 stops
American Airlines Logo
1:45 pm - 11:51 pm
SXM
-
PWM
10h 06m
1 stop
$359American Airlines
Wed, Jun 3 - Sun, Jun 7
JetBlue Logo
6:00 am - 3:35 pm
PWM
-
SXM
9h 35m
1 stop
JetBlue Logo
3:00 pm - 11:47 pm
SXM
-
PWM
8h 47m
1 stop
$395JetBlue
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
5:40 pm - 3:28 pm
PWM
-
SXM
21h 48m
2 stops
American Airlines Logo
2:24 pm - 10:46 pm
SXM
-
PWM
8h 22m
1 stop
$485American Airlines
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
7:00 am - 3:00 pm
PWM
-
SXM
8h 00m
1 stop
American Airlines Logo
2:24 pm - 10:46 pm
SXM
-
PWM
8h 22m
1 stop
$492American Airlines
Mon, Mar 30 - Wed, Apr 8
American Airlines Logo
11:59 am - 3:00 pm
PWM
-
SXM
27h 01m
1 stop
American Airlines Logo
4:28 pm - 12:14 pm
SXM
-
PWM
19h 46m
2 stops
$498American Airlines
Sun, Mar 8 - Sun, Mar 15
United Airlines Logo
4:58 pm - 12:33 pm
PWM
-
SXM
19h 35m
2 stops
United Airlines Logo
3:50 pm - 11:50 pm
SXM
-
PWM
8h 00m
1 stop
$500United Airlines
Sat, Jun 6 - Sat, Jun 13

American Airlines flights from Portland, Maine to Simpson Bay

Our best American Airlines deals on Portland, Maine to Simpson Bay flight tickets
American Airlines
Mar 8
PWM5:40 pmPortland
21h 48m
2 stops
SXM3:28 pmSimpson Bay Princess Juliana
Mar 15
SXM4:28 pmSimpson Bay Princess Juliana
19h 46m
2 stops
PWM12:14 pmPortland
$321
American Airlines
Mar 30
PWM5:40 pmPortland
19h 36m
2 stops
SXM1:16 pmSimpson Bay Princess Juliana
Apr 8
SXM12:41 pmSimpson Bay Princess Juliana
22h 34m
2 stops
PWM11:15 amPortland
$328
American Airlines
Mar 30
PWM5:40 pmPortland
21h 48m
2 stops
SXM3:28 pmSimpson Bay Princess Juliana
Apr 8
SXM12:41 pmSimpson Bay Princess Juliana
21h 13m
2 stops
PWM9:54 amPortland
$335

United Airlines flights from Portland, Maine to Simpson Bay

Our best United Airlines deals on Portland, Maine to Simpson Bay flight tickets
United Airlines
Jun 6
PWM4:58 pmPortland
19h 35m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jun 13
SXM3:50 pmSimpson Bay Princess Juliana
8h 00m
1 stop
PWM11:50 pmPortland
$500
United Airlines
Feb 7
PWM3:05 pmPortland
21h 45m
2 stops
SXM1:50 pmSimpson Bay Princess Juliana
Feb 11
SXM2:52 pmSimpson Bay Princess Juliana
9h 29m
1 stop
PWM11:21 pmPortland
$571
United Airlines
Feb 7
PWM2:31 pmPortland
22h 19m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
Feb 11
SXM2:52 pmSimpson Bay Princess Juliana
9h 29m
1 stop
PWM11:21 pmPortland
$576

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 January 29, 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

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 3/8

5:40 pm-3:28 pm

2 stops21h 48m

Simpson Bay Princess Juliana

Sun 3/15

4:28 pm-12:14 pm

2 stops19h 46m

$321

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:40 pm-1:16 pm

2 stops19h 36m

Simpson Bay Princess Juliana

Wed 4/8

12:41 pm-11:15 am

2 stops22h 34m

$328

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:40 pm-3:28 pm

2 stops21h 48m

Simpson Bay Princess Juliana

Wed 4/8

12:41 pm-9:54 am

2 stops21h 13m

$335

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:00 am-12:45 pm

1 stop6h 45m

Simpson Bay Princess Juliana

Sun 6/7

1:45 pm-9:44 pm

1 stop7h 59m

$354

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

7:35 pm-3:31 pm

2 stops19h 56m

Simpson Bay Princess Juliana

Sun 6/7

1:45 pm-11:51 pm

1 stop10h 06m

$359

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

6:00 am-3:35 pm

1 stop9h 35m

Simpson Bay Princess Juliana

Wed 4/8

3:00 pm-11:47 pm

1 stop8h 47m

$395

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

5:40 pm-3:28 pm

2 stops21h 48m

Simpson Bay Princess Juliana

Wed 4/8

2:24 pm-10:46 pm

1 stop8h 22m

$485

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 3/30

7:00 am-3:00 pm

1 stop8h 00m

Simpson Bay Princess Juliana

Wed 4/8

2:24 pm-10:46 pm

1 stop8h 22m

$492

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sun 3/8

11:59 am-3:00 pm

1 stop27h 01m

Simpson Bay Princess Juliana

Sun 3/15

4:28 pm-12:14 pm

2 stops19h 46m

$498

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

4:58 pm-12:33 pm

2 stops19h 35m

Simpson Bay Princess Juliana

Sat 6/13

3:50 pm-11:50 pm

1 stop8h 00m

$500

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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 typical price of a round-trip flight between Portland, Maine and Simpson Bay?

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 13m

Direct flights

None
The fastest flight from Portland, Maine to Simpson Bay takes 7h 13m
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 7h 13m, 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
DeltaPriceFrom $268Free CancellationRating
7.9
8,128 reviews
Search Delta flights
United AirlinesPriceFrom $305Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
American AirlinesPriceFrom $566Free CancellationRating
7.2
11,205 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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