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Cheap flights from Maine to Simpson Bay from $71

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Maine to Simpson Bay departing on 2/23. 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 Maine to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 2:31 pm
PWM
-
SXM
7h 31m1 stop
American Airlines Logo
2:42 pm - 10:54 pm
SXM
-
PWM
9h 12m1 stop
$293American Airlines
Thu, Jan 22 - Thu, Jan 29
American Airlines Logo
6:00 am - 2:31 pm
PWM
-
SXM
7h 31m1 stop
American Airlines Logo
3:31 pm - 12:06 pm
SXM
-
PWM
21h 35m2 stops
$298American Airlines
Thu, Jan 22 - Thu, Jan 29
American Airlines Logo
5:07 pm - 1:16 pm
PWM
-
SXM
20h 09m2 stops
American Airlines Logo
4:28 pm - 1:27 pm
SXM
-
PWM
20h 59m2 stops
$322American Airlines
Tue, Mar 31 - Mon, Apr 6
JetBlue Logo
8:00 am - 1:15 pm
BOS
-
SXM
4h 15mnonstop
JetBlue Logo
2:30 pm - 6:09 pm
SXM
-
BOS
4h 39mnonstop
$333JetBlue
Wed, Jan 14 - Fri, Jan 16
Multiple Airlines Logo
7:49 am - 1:05 pm
BOS
-
SXM
4h 16mnonstop
Multiple Airlines Logo
3:20 pm - 12:30 am
SXM
-
BOS
10h 10m1 stop
$335Multiple Airlines
Fri, Feb 20 - Sat, Feb 28
Multiple Airlines Logo
5:34 am - 2:15 pm
BOS
-
SXM
7h 41m1 stop
Multiple Airlines Logo
2:30 pm - 6:09 pm
SXM
-
BOS
4h 39mnonstop
$337Multiple Airlines
Mon, Feb 2 - Fri, Feb 6
JetBlue Logo
8:00 am - 1:15 pm
BOS
-
SXM
4h 15mnonstop
JetBlue Logo
12:35 pm - 8:18 pm
SXM
-
BOS
8h 43m1 stop
$339JetBlue
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
8:51 pm - 4:28 pm
BOS
-
SXM
18h 37m2 stops
American Airlines Logo
3:23 pm - 10:22 pm
SXM
-
BOS
7h 59m1 stop
$340American Airlines
Sun, Jan 11 - Sat, Jan 17
American Airlines Logo
8:51 pm - 2:22 pm
BOS
-
SXM
16h 31m2 stops
American Airlines Logo
5:33 pm - 10:29 am
SXM
-
BOS
17h 56m2 stops
$341American Airlines
Fri, Jan 16 - Tue, Jan 20
Spirit Airlines Logo
3:43 pm - 2:10 pm
BOS
-
SXM
21h 27m2 stops
Spirit Airlines Logo
3:15 pm - 11:57 pm
SXM
-
BOS
9h 42m1 stop
$343Spirit Airlines
Sun, Jan 11 - Thu, Jan 15

American Airlines flights from Maine to Simpson Bay

Our best American Airlines deals on Maine to Simpson Bay flight tickets
American Airlines
Jan 22
PWM6:00 amPortland
7h 31m
1 stop
SXM2:31 pmSimpson Bay Princess Juliana
Jan 29
SXM2:42 pmSimpson Bay Princess Juliana
9h 12m
1 stop
PWM10:54 pmPortland
$293
Find similar
American Airlines
Jan 22
PWM5:07 pmPortland
21h 15m
2 stops
SXM3:22 pmSimpson Bay Princess Juliana
Jan 29
SXM4:24 pmSimpson Bay Princess Juliana
20h 42m
2 stops
PWM12:06 pmPortland
$298
Find similar
American Airlines
Mar 31
PWM5:07 pmPortland
20h 09m
2 stops
SXM1:16 pmSimpson Bay Princess Juliana
Apr 7
SXM3:55 pmSimpson Bay Princess Juliana
20h 05m
2 stops
PWM12:00 pmPortland
$322
Find similar

United Airlines flights from Maine to Simpson Bay

Our best United Airlines deals on Maine to Simpson Bay flight tickets
United Airlines
Jan 24
BOS7:22 pmBoston Logan Intl
19h 29m
2 stops
SXM3:51 pmSimpson Bay Princess Juliana
Jan 29
SXM2:52 pmSimpson Bay Princess Juliana
20h 44m
2 stops
BOS10:36 amBoston Logan Intl
$352
Find similar
United Airlines
Jan 17
BOS6:00 amBoston Logan Intl
8h 57m
1 stop
SXM3:57 pmSimpson Bay Princess Juliana
Jan 18
SXM4:55 pmSimpson Bay Princess Juliana
27h 02m
1 stop
BOS6:57 pmBoston Logan Intl
$354
Find similar
United Airlines
Jan 16
BOS11:42 amBoston Logan Intl
27h 15m
2 stops
SXM3:57 pmSimpson Bay Princess Juliana
Jan 18
SXM4:55 pmSimpson Bay Princess Juliana
27h 02m
1 stop
BOS6:57 pmBoston Logan Intl
$359
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from 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 December 27, 2025.
Use the filters below to find and compare flights from Maine to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 1/22

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Thu 1/29

2:42 pm-10:54 pm

1 stop9h 12m

$293

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Thu 1/22

6:00 am-2:31 pm

1 stop7h 31m

Simpson Bay Princess Juliana

Thu 1/29

3:31 pm-12:06 pm

2 stops21h 35m

$298

PortlandSimpson Bay

PWM - SXM

PWMSXM

Portland

Tue 3/31

5:07 pm-1:16 pm

2 stops20h 09m

Simpson Bay Princess Juliana

Mon 4/6

4:28 pm-1:27 pm

2 stops20h 59m

$322

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 1/14

8:00 am-1:15 pm

Nonstop4h 15m

Simpson Bay Princess Juliana

Fri 1/16

2:30 pm-6:09 pm

Nonstop4h 39m

$333

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 2/20

7:49 am-1:05 pm

Nonstop4h 16m

Simpson Bay Princess Juliana

Sat 2/28

3:20 pm-12:30 am

1 stop10h 10m

$335

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 2/2

5:34 am-2:15 pm

1 stop7h 41m

Simpson Bay Princess Juliana

Fri 2/6

2:30 pm-6:09 pm

Nonstop4h 39m

$337

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

8:00 am-1:15 pm

Nonstop4h 15m

Simpson Bay Princess Juliana

Sat 1/17

12:35 pm-8:18 pm

1 stop8h 43m

$339

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

8:51 pm-4:28 pm

2 stops18h 37m

Simpson Bay Princess Juliana

Sat 1/17

3:23 pm-10:22 pm

1 stop7h 59m

$340

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 1/16

8:51 pm-2:22 pm

2 stops16h 31m

Simpson Bay Princess Juliana

Tue 1/20

5:33 pm-10:29 am

2 stops17h 56m

$341

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 1/11

3:43 pm-2:10 pm

2 stops21h 27m

Simpson Bay Princess Juliana

Thu 1/15

3:15 pm-11:57 pm

1 stop9h 42m

$343

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from 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 day to depart on your flight to Simpson Bay?

Our data shows that Tuesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $641. Flights from Maine to Simpson Bay on a Sunday will generally be more expensive and average around $1,165. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

What is the cheapest time of day to depart on your flight to Simpson Bay?

According to our data, the cheapest time of day to fly to Simpson Bay is in the afternoon. momondo users have found flights departing from Maine to Simpson Bay in the afternoon for as low as $661. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. In contrast, the most expensive time of day to depart to Simpson Bay is in the morning when prices are around $807.

Cheap Maine to Simpson Bay flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maine to Simpson Bay

Fastest flight time

4h 05m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Simpson Bay

1 airport
The fastest flight from Maine to Simpson Bay takes 4h 05m
Direct flights go from Maine to Simpson Bay on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport in Simpson Bay. From Maine there are direct flights to Simpson Bay Princess Juliana (SXM).
Search flight deals

  • When did momondo last update prices for flights from Maine to Simpson Bay Princess Juliana Airport?

    Prices for flights from Maine to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Maine to Simpson Bay Princess Juliana Airport?

  • How old do you have to be to fly from Maine 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 Maine 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.

Best airlines flying from Maine to Simpson Bay

Compare and see reviews for airlines that fly from Maine to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $268Free CancellationRating
7.9
8,018 reviews
Search Delta flights
United AirlinesPriceFrom $305Free CancellationRating
7.4
9,116 reviews
Search United Airlines flights
American AirlinesPriceFrom $566Free CancellationRating
7.2
11,067 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 Maine to Simpson Bay?

Finding the right flight to Simpson Bay from Maine is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Simpson Bay quick and easy, saving you time and money.

Can I find flights from Maine to Simpson Bay with flexible booking policies on momondo?

Yes. All flights to Simpson Bay from Maine on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Maine to Simpson Bay?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Maine to Simpson Bay.

I’m not ready to book a flight from Maine to Simpson Bay right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Maine to Simpson Bay flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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