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Cheap flights from Maine to Caribbean Islands from $66

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 Caribbean Islands departing on 9/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Maine to Caribbean Islands

Cheap round-trip flights

Spirit Airlines Logo
3:37 pm - 11:57 pmBOS-SJU
8h 20m1 stop
Spirit Airlines Logo
6:44 am - 1:48 pmSJU-BOS
7h 04m1 stop
$139Spirit Airlines
Find Deal
Tue, Sep 2 - Tue, Sep 9
Spirit Airlines Logo
11:13 am - 4:07 pmBOS-SJU
3h 54mnonstop
Spirit Airlines Logo
5:27 pm - 8:34 pmSJU-BOS
4h 07mnonstop
$144Spirit Airlines
Find Deal
Mon, Dec 29 - Fri, Jan 2
Logo
3:25 pm - 9:05 amBOS-SJU
17h 40m1 stop
Logo
8:13 pm - 8:35 amSJU-BOS
12h 22m1 stop
$199
Find Deal
Sun, Aug 17 - Thu, Aug 21
JetBlue Logo
1:40 pm - 5:42 pmBOS-SJU
4h 02mnonstop
JetBlue Logo
8:00 am - 12:03 pmSJU-BOS
4h 03mnonstop
$205JetBlue
Find Deal
Wed, Aug 27 - Wed, Sep 3
JetBlue Logo
9:40 am - 1:45 pmBOS-SJU
4h 05mnonstop
JetBlue Logo
7:55 pm - 11:57 pmSJU-BOS
4h 02mnonstop
$206JetBlue
Find Deal
Fri, Aug 22 - Fri, Sep 5
Logo
12:20 pm - 8:56 pmBOS-SJU
8h 36m1 stop
Logo
8:00 am - 9:18 amSJU-BOS
25h 18m1 stop
$219
Find Deal
Tue, Sep 9 - Sat, Sep 13
American Airlines Logo
7:36 am - 4:00 pmBOS-STT
8h 24m1 stop
American Airlines Logo
1:40 pm - 12:59 amSTT-BOS
11h 19m1 stop
$311American Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
Delta Logo
6:37 am - 12:35 pmBOS-AUA
4h 58mnonstop
Delta Logo
1:50 pm - 5:54 pmAUA-BOS
5h 04mnonstop
$321Delta
Find Deal
Mon, Jan 12 - Fri, Jan 23
Delta Logo
7:25 pm - 1:55 pmBOS-AUA
17h 30m1 stop
Delta Logo
1:50 pm - 5:54 pmAUA-BOS
5h 04mnonstop
$325Delta
Find Deal
Sat, Jan 10 - Fri, Jan 23
American Airlines Logo
7:45 am - 3:25 pmBOS-PUJ
7h 40m1 stop
American Airlines Logo
1:35 pm - 12:15 amPUJ-BOS
10h 40m2 stops
$335American Airlines
Find Deal
Thu, Sep 4 - Wed, Sep 10

Spirit Airlines flights from Maine to Caribbean Islands

Our best Spirit Airlines deals on Maine to Caribbean Islands flight tickets
Spirit Airlines
Sep 2
BOS3:37 pmBoston Logan Intl
8h 20m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Sep 9
SJU6:44 amSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
BOS1:48 pmBoston Logan Intl
$139
Find similar
Spirit Airlines
Dec 29
BOS11:13 amBoston Logan Intl
3h 54m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Jan 2
SJU5:27 pmSan Juan Luis Munoz Marin Intl
4h 07m
BOS8:34 pmBoston Logan Intl
$144
Find similar
Spirit Airlines
Sep 2
BOS3:37 pmBoston Logan Intl
8h 20m
1 stop
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Sep 6
SJU6:44 amSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
BOS1:48 pmBoston Logan Intl
$150
Find similar

JetBlue flights from Maine to Caribbean Islands

Our best JetBlue deals on Maine to Caribbean Islands flight tickets
JetBlue
Aug 27
BOS1:40 pmBoston Logan Intl
4h 02m
SJU5:42 pmSan Juan Luis Munoz Marin Intl
Sep 3
SJU8:00 amSan Juan Luis Munoz Marin Intl
4h 03m
BOS12:03 pmBoston Logan Intl
$205
Find similar
JetBlue
Aug 22
BOS9:40 amBoston Logan Intl
4h 05m
SJU1:45 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU7:55 pmSan Juan Luis Munoz Marin Intl
4h 02m
BOS11:57 pmBoston Logan Intl
$206
Find similar
JetBlue
Aug 18
BOS8:45 pmBoston Logan Intl
4h 04m
SJU12:49 amSan Juan Luis Munoz Marin Intl
Aug 27
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 07m
BOS10:07 amBoston Logan Intl
$208
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Maine to Caribbean Islands 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 1, 2025.
Use the filters below to find and compare flights from Maine to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 9/2

3:37 pm-11:57 pm

1 stop8h 20m

San Juan Luis Munoz Marin Intl

Tue 9/9

6:44 am-1:48 pm

1 stop7h 04m

$139

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Mon 12/29

11:13 am-4:07 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Fri 1/2

5:27 pm-8:34 pm

Nonstop4h 07m

$144

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Sun 8/17

3:25 pm-9:05 am

1 stop17h 40m

San Juan Luis Munoz Marin Intl

Thu 8/21

8:13 pm-8:35 am

1 stop12h 22m

$199

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Wed 8/27

1:40 pm-5:42 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 9/3

8:00 am-12:03 pm

Nonstop4h 03m

$205

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Fri 8/22

9:40 am-1:45 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Fri 9/5

7:55 pm-11:57 pm

Nonstop4h 02m

$206

BostonSan Juan

BOS - SJU

BOSSJU

Boston Logan Intl

Tue 9/9

12:20 pm-8:56 pm

1 stop8h 36m

San Juan Luis Munoz Marin Intl

Sat 9/13

8:00 am-9:18 am

1 stop25h 18m

$219

BostonSaint Thomas Island

BOS - STT

BOSSTT

Boston Logan Intl

Sat 9/27

7:36 am-4:00 pm

1 stop8h 24m

Saint Thomas Island Cyril E King

Sat 10/4

1:40 pm-12:59 am

1 stop11h 19m

$311

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Mon 1/12

6:37 am-12:35 pm

Nonstop4h 58m

Oranjestad Reina Beatrix

Fri 1/23

1:50 pm-5:54 pm

Nonstop5h 04m

$321

BostonOranjestad

BOS - AUA

BOSAUA

Boston Logan Intl

Sat 1/10

7:25 pm-1:55 pm

1 stop17h 30m

Oranjestad Reina Beatrix

Fri 1/23

1:50 pm-5:54 pm

Nonstop5h 04m

$325

BostonPunta Cana

BOS - PUJ

BOSPUJ

Boston Logan Intl

Thu 9/4

7:45 am-3:25 pm

1 stop7h 40m

Punta Cana

Wed 9/10

1:35 pm-12:15 am

2 stops10h 40m

$335

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 Caribbean Islands from

How to get the cheapest flight ticket from Maine to Caribbean Islands

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 Caribbean Islands?

The month of August is, on average, the cheapest month to fly to Caribbean Islands from Maine, with most prices found around $262. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Maine averaging around $275.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Maine to Caribbean Islands is on a Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $334. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $579. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Maine to Caribbean Islands in the evening for as low as $302. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $557. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $450 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Maine for as low as $359 on momondo.

Can stopping save me money on Maine to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Maine to Caribbean Islands.

Cheap Maine to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Maine to Caribbean Islands

Best Price Found

$66

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean Islands

9 airports
The best one-way flight to Caribbean Islands from Maine in the past 72 hours is $66. The best round-trip flight deal from Maine to Caribbean Islands found on momondo in the last 72 hours is $139.
The fastest flight from Maine to Caribbean Islands takes 3h 21m
Direct flights go from Maine to Caribbean Islands every day.
There are 9 airports near Caribbean Islands: Nassau Intl (NAS), Santo Domingo Las Americas (SDQ), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Providenciales (PLS), Simpson Bay Princess Juliana (SXM), Santiago de los Caballeros (STI), San Juan Luis Munoz Marin Intl (SJU)
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  • When did momondo last update prices for flights from Maine to Caribbean Islands?

    Prices for flights from Maine to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Maine to Caribbean Islands?

  • How old do you have to be to fly from Maine to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Maine to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Maine to Caribbean Islands?

Best airlines flying from Maine to Caribbean Islands

Compare and see reviews for airlines that fly from Maine to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $145Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
JetBluePriceFrom $214Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $274Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $285Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $322Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $401Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Maine to Caribbean Islands?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean Islands from Maine.

Can I find flights from Maine to Caribbean Islands with flexible booking policies on momondo?

All flight searches from Maine to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Maine to Caribbean Islands?

momondo helps you find the best flight between Maine and Caribbean Islands by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes momondo offers price alerts on flights to Caribbean Islands from Maine. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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