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Cheap flights from Portland, Maine to Simpson Bay from $380

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 10/16. 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.
American Airlines Logo
7:26 pm - 1:23 pmPWM  Portland-SXM Simpson Bay Princess Juliana
17h 57m2 stops Philadelphia Miami
American Airlines Logo
4:39 pm - 3:43 pmSXM  Simpson Bay Princess Juliana-PWM Portland
23h 04m2 stops Miami Washington, D.C. Reagan-National
$380American Airlines
Fri, Oct 16 - Fri, Oct 23
American Airlines Logo
5:05 pm - 1:23 pmPWM  Portland-SXM Simpson Bay Princess Juliana
20h 18m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
2:23 pm - 9:52 amSXM  Simpson Bay Princess Juliana-PWM Portland
19h 29m2 stops Miami Washington, D.C. Reagan-National
$380American Airlines
Fri, Sep 25 - Fri, Oct 2
American Airlines Logo
6:42 pm - 4:30 pmPWM  Portland-SXM Simpson Bay Princess Juliana
20h 48m2 stops Philadelphia Miami
American Airlines Logo
5:33 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-PWM Portland
19h 32m2 stops Miami Philadelphia
$387American Airlines
Mon, Jan 4 - Fri, Jan 8
American Airlines Logo
6:42 pm - 4:30 pmPWM  Portland-SXM Simpson Bay Princess Juliana
20h 48m2 stops Philadelphia Miami
American Airlines Logo
2:50 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-PWM Portland
22h 15m2 stops Charlotte Douglas Philadelphia
$387American Airlines
Mon, Jan 4 - Fri, Jan 8
Delta Logo
6:00 am - 2:45 pmPWM  Portland-SXM Simpson Bay Princess Juliana
7h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:10 pm - 12:08 pmSXM  Simpson Bay Princess Juliana-PWM Portland
20h 58m2 stops Atlanta Hartsfield-Jackson Detroit Metropolitan Wayne County
$487Delta
Tue, Nov 10 - Tue, Nov 17
United Airlines Logo
6:00 am - 1:50 pmPWM  Portland-SXM Simpson Bay Princess Juliana
6h 50m1 stop Newark
United Airlines Logo
2:52 pm - 9:27 pmSXM  Simpson Bay Princess Juliana-PWM Portland
31h 35m2 stops Newark Chicago O'Hare Intl
$507United Airlines
Tue, Feb 2 - Thu, Feb 4
United Airlines Logo
6:00 am - 1:50 pmPWM  Portland-SXM Simpson Bay Princess Juliana
6h 50m1 stop Newark
United Airlines Logo
2:52 pm - 9:27 pmSXM  Simpson Bay Princess Juliana-PWM Portland
31h 35m2 stops Newark Chicago O'Hare Intl
$523United Airlines
Tue, Feb 2 - Thu, Feb 4
United Airlines Logo
9:45 am - 1:50 pmPWM  Portland-SXM Simpson Bay Princess Juliana
27h 05m2 stops Chicago O'Hare Intl Newark
United Airlines Logo
2:52 pm - 9:27 pmSXM  Simpson Bay Princess Juliana-PWM Portland
31h 35m2 stops Newark Chicago O'Hare Intl
$544United Airlines
Tue, Feb 2 - Thu, Feb 4
Delta Logo
6:00 am - 1:53 pmPWM  Portland-SXM Simpson Bay Princess Juliana
7h 53m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:18 pm - 11:28 pmSXM  Simpson Bay Princess Juliana-PWM Portland
8h 10m1 stop Atlanta Hartsfield-Jackson
$547Delta
Fri, Sep 25 - Fri, Oct 2
JetBlue Logo
6:00 am - 1:25 pmPWM  Portland-SXM Simpson Bay Princess Juliana
7h 25m1 stop New York John F Kennedy Intl
JetBlue Logo
2:45 pm - 11:52 pmSXM  Simpson Bay Princess Juliana-PWM Portland
9h 07m1 stop New York John F Kennedy Intl
$561JetBlue
Tue, Oct 20 - Fri, Oct 23

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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
Sep 25
PWM5:05 pmPortland
20h 18m
2 stops
SXM1:23 pmSimpson Bay Princess Juliana
Oct 2
SXM2:23 pmSimpson Bay Princess Juliana
19h 29m
2 stops
PWM9:52 amPortland
$380
American Airlines
Jan 4
PWM5:41 amPortland
7h 48m
1 stop
SXM2:29 pmSimpson Bay Princess Juliana
Jan 8
SXM5:33 pmSimpson Bay Princess Juliana
19h 33m
2 stops
PWM12:06 pmPortland
$387
American Airlines
Jan 4
PWM5:41 amPortland
7h 48m
1 stop
SXM2:29 pmSimpson Bay Princess Juliana
Jan 8
SXM3:50 pmSimpson Bay Princess Juliana
21h 15m
1 stop
PWM12:05 pmPortland
$389

Delta flights from Portland, Maine to Simpson Bay

Our best Delta deals on Portland, Maine to Simpson Bay flight tickets
Delta
Nov 10
PWM6:00 amPortland
7h 45m
1 stop
SXM2:45 pmSimpson Bay Princess Juliana
Nov 17
SXM4:10 pmSimpson Bay Princess Juliana
20h 58m
2 stops
PWM12:08 pmPortland
$487
Delta
Sep 25
PWM6:00 amPortland
7h 53m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 2
SXM3:18 pmSimpson Bay Princess Juliana
8h 10m
1 stop
PWM11:28 pmPortland
$547
Delta
Oct 16
PWM6:01 amPortland
7h 39m
1 stop
SXM1:40 pmSimpson Bay Princess Juliana
Oct 23
SXM3:05 pmSimpson Bay Princess Juliana
8h 30m
1 stop
PWM11:35 pmPortland
$627

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 August 12, 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 Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Fri 10/16

7:26 pm-1:23 pm

2 stops17h 57m

Simpson Bay Princess Juliana

Fri 10/23

4:39 pm-3:43 pm

2 stops23h 04m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Fri 9/25

5:05 pm-1:23 pm

2 stops20h 18m

Simpson Bay Princess Juliana

Fri 10/2

2:23 pm-9:52 am

2 stops19h 29m

$380

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Mon 1/4

6:42 pm-4:30 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Fri 1/8

5:33 pm-12:05 pm

2 stops19h 32m

$387

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Mon 1/4

6:42 pm-4:30 pm

2 stops20h 48m

Simpson Bay Princess Juliana

Fri 1/8

2:50 pm-12:05 pm

2 stops22h 15m

$387

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 11/10

6:00 am-2:45 pm

1 stop7h 45m

Simpson Bay Princess Juliana

Tue 11/17

4:10 pm-12:08 pm

2 stops20h 58m

$487

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 2/2

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 2/4

2:52 pm-9:27 pm

2 stops31h 35m

$507

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 2/2

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Thu 2/4

2:52 pm-9:27 pm

2 stops31h 35m

$523

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 2/2

9:45 am-1:50 pm

2 stops27h 05m

Simpson Bay Princess Juliana

Thu 2/4

2:52 pm-9:27 pm

2 stops31h 35m

$544
Quickest round-trip

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Fri 9/25

6:00 am-1:53 pm

1 stop7h 53m

Simpson Bay Princess Juliana

Fri 10/2

3:18 pm-11:28 pm

1 stop8h 10m

$547

PortlandSimpson Bay

PWM Portland - SXM Simpson Bay Princess Juliana

PWMSXM

Portland

Tue 10/20

6:00 am-1:25 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Fri 10/23

2:45 pm-11:52 pm

1 stop9h 07m

$561

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 63% 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

6h 50m

Direct flights

None
The fastest flight from Portland, Maine to Simpson Bay takes 6h 50m
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 6h 50m, 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
10,111 reviews
Search United Airlines flights
American AirlinesPriceFrom $583Free CancellationRating
7.1
11,911 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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