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Cheap flights from Maine to Simpson Bay from $118

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 12/8. 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

United Airlines Logo
6:00 am - 12:50 pmBOS-SXM
6h 50m1 stop
United Airlines Logo
1:52 pm - 10:47 pmSXM-BOS
8h 55m1 stop
$317United Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
6:15 pm - 2:19 pmBOS-SXM
19h 04m2 stops
American Airlines Logo
5:24 pm - 9:33 amSXM-BOS
17h 09m2 stops
$322American Airlines
Find Deal
Sat, Nov 8 - Wed, Nov 12
Spirit Airlines Logo
5:45 am - 3:10 pmBOS-SXM
8h 25m1 stop
Spirit Airlines Logo
4:28 pm - 12:40 amSXM-BOS
9h 12m1 stop
$342Spirit Airlines
Find Deal
Wed, Nov 5 - Sat, Nov 15
Spirit Airlines Logo
8:24 pm - 2:00 pmBOS-SXM
17h 36m1 stop
Spirit Airlines Logo
3:05 pm - 11:59 pmSXM-BOS
8h 54m1 stop
$347Spirit Airlines
Find Deal
Fri, Oct 17 - Fri, Oct 24
Delta Logo
8:45 pm - 12:15 pmBOS-SXM
14h 30m1 stop
Delta Logo
4:26 pm - 7:24 amSXM-BOS
15h 58m1 stop
$363Delta
Find Deal
Sat, Jan 17 - Thu, Jan 22
Delta Logo
9:00 pm - 2:00 pmBOS-SXM
16h 00m1 stop
Delta Logo
4:20 pm - 1:30 amSXM-BOS
10h 10m1 stop
$383Delta
Find Deal
Fri, Nov 7 - Thu, Nov 13
Multiple Airlines Logo
6:40 pm - 2:40 pmBOS-SXM
19h 00m1 stop
Multiple Airlines Logo
4:28 pm - 12:40 amSXM-BOS
9h 12m1 stop
$386Multiple Airlines
Find Deal
Fri, Nov 28 - Wed, Dec 10
JetBlue Logo
7:35 am - 12:00 pmBOS-SXM
4h 25mnonstop
JetBlue Logo
1:00 pm - 5:36 pmSXM-BOS
4h 36mnonstop
$388JetBlue
Find Deal
Sun, Oct 19 - Sat, Oct 25
JetBlue Logo
11:43 am - 4:54 pmBOS-SXM
4h 11mnonstop
JetBlue Logo
6:00 pm - 9:27 pmSXM-BOS
4h 27mnonstop
$389JetBlue
Find Deal
Sat, Nov 29 - Sat, Dec 6
Multiple Airlines Logo
6:40 pm - 2:40 pmBOS-SXM
19h 00m1 stop
Multiple Airlines Logo
4:28 pm - 12:40 amSXM-BOS
9h 12m1 stop
$391Multiple Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 8

American Airlines flights from Maine to Simpson Bay

Our best American Airlines deals on Maine to Simpson Bay flight tickets
American Airlines
Nov 8
BOS6:15 pmBoston Logan Intl
19h 04m
2 stops
SXM2:19 pmSimpson Bay Princess Juliana
Nov 12
SXM5:24 pmSimpson Bay Princess Juliana
17h 09m
2 stops
BOS9:33 amBoston Logan Intl
$322
Find similar
American Airlines
Nov 8
BOS5:08 pmBoston Logan Intl
19h 52m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Nov 12
SXM5:24 pmSimpson Bay Princess Juliana
8h 27m
1 stop
BOS12:51 amBoston Logan Intl
$324
Find similar
American Airlines
Nov 8
BOS6:15 pmBoston Logan Intl
18h 45m
1 stop
SXM2:00 pmSimpson Bay Princess Juliana
Nov 15
SXM5:24 pmSimpson Bay Princess Juliana
17h 32m
2 stops
BOS9:56 amBoston Logan Intl
$329
Find similar

JetBlue flights from Maine to Simpson Bay

Our best JetBlue deals on Maine to Simpson Bay flight tickets
JetBlue
Oct 19
BOS7:35 amBoston Logan Intl
4h 25m
SXM12:00 pmSimpson Bay Princess Juliana
Oct 25
SXM1:00 pmSimpson Bay Princess Juliana
4h 36m
BOS5:36 pmBoston Logan Intl
$388
Find similar
JetBlue
Nov 29
BOS11:43 amBoston Logan Intl
4h 11m
SXM4:54 pmSimpson Bay Princess Juliana
Dec 6
SXM6:00 pmSimpson Bay Princess Juliana
4h 27m
BOS9:27 pmBoston Logan Intl
$389
Find similar
JetBlue
Dec 14
BOS8:30 amBoston Logan Intl
7h 33m
1 stop
SXM5:03 pmSimpson Bay Princess Juliana
Dec 21
SXM1:59 pmSimpson Bay Princess Juliana
4h 35m
BOS5:34 pmBoston Logan Intl
$395
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 September 25, 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

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Mon 10/27

6:00 am-12:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 10/31

1:52 pm-10:47 pm

1 stop8h 55m

$317

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/8

6:15 pm-2:19 pm

2 stops19h 04m

Simpson Bay Princess Juliana

Wed 11/12

5:24 pm-9:33 am

2 stops17h 09m

$322

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 11/5

5:45 am-3:10 pm

1 stop8h 25m

Simpson Bay Princess Juliana

Sat 11/15

4:28 pm-12:40 am

1 stop9h 12m

$342

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 10/17

8:24 pm-2:00 pm

1 stop17h 36m

Simpson Bay Princess Juliana

Fri 10/24

3:05 pm-11:59 pm

1 stop8h 54m

$347

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 1/17

8:45 pm-12:15 pm

1 stop14h 30m

Simpson Bay Princess Juliana

Thu 1/22

4:26 pm-7:24 am

1 stop15h 58m

$363

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 11/7

9:00 pm-2:00 pm

1 stop16h 00m

Simpson Bay Princess Juliana

Thu 11/13

4:20 pm-1:30 am

1 stop10h 10m

$383

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Fri 11/28

6:40 pm-2:40 pm

1 stop19h 00m

Simpson Bay Princess Juliana

Wed 12/10

4:28 pm-12:40 am

1 stop9h 12m

$386

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sun 10/19

7:35 am-12:00 pm

Nonstop4h 25m

Simpson Bay Princess Juliana

Sat 10/25

1:00 pm-5:36 pm

Nonstop4h 36m

$388

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Sat 11/29

11:43 am-4:54 pm

Nonstop4h 11m

Simpson Bay Princess Juliana

Sat 12/6

6:00 pm-9:27 pm

Nonstop4h 27m

$389

BostonSimpson Bay

BOS - SXM

BOSSXM

Boston Logan Intl

Wed 12/3

6:40 pm-2:40 pm

1 stop19h 00m

Simpson Bay Princess Juliana

Mon 12/8

4:28 pm-12:40 am

1 stop9h 12m

$391

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 month to fly to Simpson Bay?

In general, September is the cheapest month to fly from Maine to Simpson Bay. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $480. If you aren’t able to travel to Simpson Bay during the month of September, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $508.

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

Our data shows that Wednesday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $526. Flights from Maine to Simpson Bay on a Friday will generally be more expensive and average around $935. 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 at noon. momondo users have found flights departing from Maine to Simpson Bay at noon for as low as $299. 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 $676.

How far in advance should I book a flight to Simpson Bay?

You are more likely to see cheaper flights to Simpson Bay from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Simpson Bay for around $601 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Simpson Bay from Maine for as low as $553 on momondo.

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 08m

Direct flights

Every day

Airports in Simpson Bay

1 airport
The fastest flight from Maine to Simpson Bay takes 4h 08m
Direct flights go from Maine to Simpson Bay every day.
There is 1 airport near Simpson Bay: 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 $286Free CancellationRating
7.9
7,973 reviews
Search Delta flights
United AirlinesPriceFrom $540Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights
American AirlinesPriceFrom $566Free CancellationRating
7.2
10,000 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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Airlines are sorted and displayed according to clicks in the past 7 days on momondo
Delta
American Airlines
United Airlines
Turkish Airlines
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British Airways
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Emirates