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Cheap flights from Portland, Maine to Simpson Bay from $405

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 6/6. 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.
United Airlines Logo
5:15 am - 12:33 pm
PWM
-
SXM
7h 18m
1 stop
United Airlines Logo
1:35 pm - 11:30 pm
SXM
-
PWM
9h 55m
1 stop
$405United Airlines
Sat, Jun 6 - Wed, Jun 10
American Airlines Logo
5:58 pm - 11:14 am
PWM
-
SXM
17h 16m
1 stop
American Airlines Logo
2:51 pm - 10:31 am
SXM
-
PWM
19h 40m
2 stops
$408American Airlines
Fri, Jun 26 - Fri, Jul 3
United Airlines Logo
8:16 pm - 12:33 pm
PWM
-
SXM
16h 17m
2 stops
United Airlines Logo
1:35 pm - 11:30 pm
SXM
-
PWM
9h 55m
1 stop
$410United Airlines
Sat, Jun 6 - Wed, Jun 10
American Airlines Logo
6:00 am - 3:42 pm
PWM
-
SXM
9h 42m
2 stops
American Airlines Logo
4:43 pm - 2:24 pm
SXM
-
PWM
21h 41m
2 stops
$413American Airlines
Wed, Jun 3 - Mon, Jun 8
American Airlines Logo
6:00 am - 12:40 pm
PWM
-
SXM
6h 40m
1 stop
American Airlines Logo
4:43 pm - 2:24 pm
SXM
-
PWM
21h 41m
2 stops
$415American Airlines
Wed, Jun 3 - Mon, Jun 8
United Airlines Logo
5:15 am - 12:33 pm
PWM
-
SXM
7h 18m
1 stop
United Airlines Logo
1:35 pm - 11:30 pm
SXM
-
PWM
9h 55m
1 stop
$480United Airlines
Sat, Jun 6 - Tue, Jun 9
United Airlines Logo
8:16 pm - 12:33 pm
PWM
-
SXM
16h 17m
2 stops
United Airlines Logo
1:35 pm - 11:30 pm
SXM
-
PWM
9h 55m
1 stop
$485United Airlines
Sat, Jun 6 - Tue, Jun 9
American Airlines Logo
6:54 pm - 1:22 pm
PWM
-
SXM
18h 28m
2 stops
American Airlines Logo
2:53 pm - 11:29 am
SXM
-
PWM
20h 36m
2 stops
$520American Airlines
Sat, Jun 6 - Tue, Jun 9
Delta Logo
6:25 am - 2:15 pm
PWM
-
SXM
7h 50m
1 stop
Delta Logo
3:35 pm - 12:59 am
SXM
-
PWM
9h 24m
1 stop
$523Delta
Sat, Jul 4 - Sat, Jul 11
American Airlines Logo
5:04 pm - 1:50 pm
PWM
-
SXM
20h 46m
2 stops
American Airlines Logo
4:45 pm - 2:16 pm
SXM
-
PWM
21h 31m
2 stops
$526American Airlines
Fri, Jun 26 - Fri, Jul 3

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
PWM5:15 amPortland
7h 18m
1 stop
SXM12:33 pmSimpson Bay Princess Juliana
Jun 10
SXM1:35 pmSimpson Bay Princess Juliana
9h 55m
1 stop
PWM11:30 pmPortland
$405
United Airlines
Jun 6
PWM8:16 pmPortland
16h 17m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jun 10
SXM1:35 pmSimpson Bay Princess Juliana
9h 55m
1 stop
PWM11:30 pmPortland
$410
United Airlines
Jun 6
PWM5:15 amPortland
7h 18m
1 stop
SXM12:33 pmSimpson Bay Princess Juliana
Jun 9
SXM1:35 pmSimpson Bay Princess Juliana
9h 55m
1 stop
PWM11:30 pmPortland
$480

JetBlue flights from Portland, Maine to Simpson Bay

Our best JetBlue deals on Portland, Maine to Simpson Bay flight tickets
JetBlue
Aug 31
PWM6:00 amPortland
7h 42m
1 stop
SXM1:42 pmSimpson Bay Princess Juliana
Sep 3
SXM11:20 amSimpson Bay Princess Juliana
12h 54m
1 stop
PWM12:14 amPortland
$533
JetBlue
Aug 31
PWM6:00 amPortland
7h 42m
1 stop
SXM1:42 pmSimpson Bay Princess Juliana
Sep 3
SXM11:20 amSimpson Bay Princess Juliana
12h 54m
1 stop
PWM12:14 amPortland
$571
JetBlue
Aug 31
PWM6:00 amPortland
7h 42m
1 stop
SXM1:42 pmSimpson Bay Princess Juliana
Sep 3
SXM11:20 amSimpson Bay Princess Juliana
12h 54m
1 stop
PWM12:14 amPortland
$636

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 May 7, 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
Quickest round-trip

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

5:15 am-12:33 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Wed 6/10

1:35 pm-11:30 pm

1 stop9h 55m

$405

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 6/26

5:58 pm-11:14 am

1 stop17h 16m

Simpson Bay Princess Juliana

Fri 7/3

2:51 pm-10:31 am

2 stops19h 40m

$408

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

8:16 pm-12:33 pm

2 stops16h 17m

Simpson Bay Princess Juliana

Wed 6/10

1:35 pm-11:30 pm

1 stop9h 55m

$410

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:00 am-3:42 pm

2 stops9h 42m

Simpson Bay Princess Juliana

Mon 6/8

4:43 pm-2:24 pm

2 stops21h 41m

$413

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:00 am-12:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Mon 6/8

4:43 pm-2:24 pm

2 stops21h 41m

$415

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

5:15 am-12:33 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Tue 6/9

1:35 pm-11:30 pm

1 stop9h 55m

$480

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

8:16 pm-12:33 pm

2 stops16h 17m

Simpson Bay Princess Juliana

Tue 6/9

1:35 pm-11:30 pm

1 stop9h 55m

$485

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

6:54 pm-1:22 pm

2 stops18h 28m

Simpson Bay Princess Juliana

Tue 6/9

2:53 pm-11:29 am

2 stops20h 36m

$520

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 7/4

6:25 am-2:15 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Sat 7/11

3:35 pm-12:59 am

1 stop9h 24m

$523

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Fri 6/26

5:04 pm-1:50 pm

2 stops20h 46m

Simpson Bay Princess Juliana

Fri 7/3

4:45 pm-2:16 pm

2 stops21h 31m

$526

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

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 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 64% 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 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
DeltaPriceFrom $113Free CancellationRating
7.9
8,459 reviews
Search Delta flights
American AirlinesPriceFrom $583Free CancellationRating
7.1
11,669 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
JetBlue
American Airlines
United Airlines
Delta
Spirit Airlines
Air Canada