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Cheap flights from Portland, Maine to Simpson Bay from $281

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 3/28. 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.
JetBlue Logo
6:00 am - 4:09 pm
PWM
-
SXM
10h 09m
1 stop
JetBlue Logo
3:05 pm - 11:56 pm
SXM
-
PWM
8h 51m
1 stop
$365JetBlue
Sat, May 30 - Wed, Jun 3
American Airlines Logo
6:01 pm - 1:21 pm
PWM
-
SXM
19h 20m
2 stops
American Airlines Logo
2:21 pm - 10:18 am
SXM
-
PWM
19h 57m
2 stops
$397American Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
3:39 pm - 11:37 am
PWM
-
SXM
19h 58m
2 stops
American Airlines Logo
2:21 pm - 10:18 am
SXM
-
PWM
19h 57m
2 stops
$404American Airlines
Mon, May 4 - Mon, May 11
American Airlines Logo
11:57 am - 1:21 pm
PWM
-
SXM
25h 24m
1 stop
American Airlines Logo
2:21 pm - 10:18 am
SXM
-
PWM
19h 57m
2 stops
$412American Airlines
Mon, May 4 - Mon, May 11
American Airlines Logo
6:54 pm - 3:42 pm
PWM
-
SXM
20h 48m
2 stops
American Airlines Logo
4:43 pm - 2:24 pm
SXM
-
PWM
21h 41m
2 stops
$414American Airlines
Wed, Jun 3 - Sun, Jun 7
United Airlines Logo
5:15 am - 12:33 pm
PWM
-
SXM
7h 18m
1 stop
United Airlines Logo
3:50 pm - 11:51 pm
SXM
-
PWM
8h 01m
1 stop
$419United Airlines
Wed, Jun 3 - Sun, Jun 7
JetBlue Logo
6:00 am - 1:44 pm
PWM
-
SXM
7h 44m
1 stop
JetBlue Logo
11:10 am - 11:57 pm
SXM
-
PWM
12h 47m
1 stop
$424JetBlue
Sat, Jun 6 - Sat, Jun 13
JetBlue Logo
6:00 am - 1:44 pm
PWM
-
SXM
7h 44m
1 stop
JetBlue Logo
3:05 pm - 11:56 pm
SXM
-
PWM
8h 51m
1 stop
$451JetBlue
Wed, Jun 3 - Sun, Jun 7
American Airlines Logo
7:23 pm - 1:20 pm
PWM
-
SXM
17h 57m
2 stops
American Airlines Logo
4:35 pm - 11:15 am
SXM
-
PWM
18h 40m
2 stops
$471American Airlines
Tue, Apr 7 - Tue, Apr 14
JetBlue Logo
6:00 am - 1:28 pm
PWM
-
SXM
7h 28m
1 stop
JetBlue Logo
3:02 pm - 11:58 pm
SXM
-
PWM
8h 56m
1 stop
$477JetBlue
Tue, Mar 31 - Fri, Apr 10

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 3
PWM5:15 amPortland
7h 18m
1 stop
SXM12:33 pmSimpson Bay Princess Juliana
Jun 7
SXM3:50 pmSimpson Bay Princess Juliana
8h 01m
1 stop
PWM11:51 pmPortland
$419
United Airlines
May 30
PWM4:58 pmPortland
19h 35m
2 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jun 3
SXM3:50 pmSimpson Bay Princess Juliana
8h 01m
1 stop
PWM11:51 pmPortland
$514
United Airlines
May 30
PWM6:00 amPortland
30h 33m
3 stops
SXM12:33 pmSimpson Bay Princess Juliana
Jun 3
SXM3:50 pmSimpson Bay Princess Juliana
8h 01m
1 stop
PWM11:51 pmPortland
$588

American Airlines flights from Portland, Maine to Simpson Bay

Our best American Airlines deals on Portland, Maine to Simpson Bay flight tickets
American Airlines
Apr 30
PWM6:01 pmPortland
19h 20m
2 stops
SXM1:21 pmSimpson Bay Princess Juliana
May 7
SXM2:21 pmSimpson Bay Princess Juliana
19h 57m
2 stops
PWM10:18 amPortland
$397
American Airlines
May 4
PWM3:39 pmPortland
19h 58m
2 stops
SXM11:37 amSimpson Bay Princess Juliana
May 11
SXM2:21 pmSimpson Bay Princess Juliana
19h 57m
2 stops
PWM10:18 amPortland
$404
American Airlines
May 4
PWM11:57 amPortland
25h 24m
1 stop
SXM1:21 pmSimpson Bay Princess Juliana
May 11
SXM2:21 pmSimpson Bay Princess Juliana
19h 57m
2 stops
PWM10:18 amPortland
$412

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 March 21, 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 5/30

6:00 am-4:09 pm

1 stop10h 09m

Simpson Bay Princess Juliana

Wed 6/3

3:05 pm-11:56 pm

1 stop8h 51m

$365

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 4/30

6:01 pm-1:21 pm

2 stops19h 20m

Simpson Bay Princess Juliana

Thu 5/7

2:21 pm-10:18 am

2 stops19h 57m

$397

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 5/4

3:39 pm-11:37 am

2 stops19h 58m

Simpson Bay Princess Juliana

Mon 5/11

2:21 pm-10:18 am

2 stops19h 57m

$404

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Mon 5/4

11:57 am-1:21 pm

1 stop25h 24m

Simpson Bay Princess Juliana

Mon 5/11

2:21 pm-10:18 am

2 stops19h 57m

$412

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:54 pm-3:42 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Sun 6/7

4:43 pm-2:24 pm

2 stops21h 41m

$414
Quickest round-trip

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

5:15 am-12:33 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Sun 6/7

3:50 pm-11:51 pm

1 stop8h 01m

$419

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Sat 6/6

6:00 am-1:44 pm

1 stop7h 44m

Simpson Bay Princess Juliana

Sat 6/13

11:10 am-11:57 pm

1 stop12h 47m

$424

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Wed 6/3

6:00 am-1:44 pm

1 stop7h 44m

Simpson Bay Princess Juliana

Sun 6/7

3:05 pm-11:56 pm

1 stop8h 51m

$451

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 4/7

7:23 pm-1:20 pm

2 stops17h 57m

Simpson Bay Princess Juliana

Tue 4/14

4:35 pm-11:15 am

2 stops18h 40m

$471

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 3/31

6:00 am-1:28 pm

1 stop7h 28m

Simpson Bay Princess Juliana

Fri 4/10

3:02 pm-11:58 pm

1 stop8h 56m

$477

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 44m

Direct flights

None
The fastest flight from Portland, Maine to Simpson Bay takes 7h 44m
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 44m, 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
8,313 reviews
Search Delta flights
American AirlinesPriceFrom $573Free CancellationRating
7.1
11,488 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
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United Airlines
Delta
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Air Canada