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Cheap flights from Caribbean to Boston from $106

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Caribbean to Boston departing on 12/25. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
6:00 am - 3:31 pm
SJU
-
PWM
10h 31m2 stops
American Airlines Logo
6:00 am - 11:56 pm
PWM
-
SJU
16h 56m1 stop
$231American Airlines
Wed, Feb 4 - Sun, Feb 8
American Airlines Logo
8:20 am - 10:54 pm
SJU
-
PWM
15h 34m2 stops
American Airlines Logo
5:20 am - 5:03 pm
PWM
-
SJU
10h 43m2 stops
$303American Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
2:05 am - 3:14 pm
SJU
-
PWM
14h 09m2 stops
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m1 stop
$356United Airlines
Mon, Mar 2 - Wed, Mar 4
United Airlines Logo
8:10 am - 2:23 pm
SJU
-
PWM
7h 13m1 stop
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m1 stop
$411United Airlines
Tue, Mar 3 - Wed, Mar 4
American Airlines Logo
5:40 am - 4:36 pm
SJU
-
PWM
10h 56m2 stops
American Airlines Logo
6:01 am - 1:52 pm
PWM
-
SJU
7h 51m1 stop
$433American Airlines
Fri, May 1 - Sat, May 16
United Airlines Logo
8:10 am - 2:23 pm
SJU
-
PWM
7h 13m1 stop
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m1 stop
$505United Airlines
Tue, Mar 3 - Wed, Mar 4
American Airlines Logo
5:40 am - 4:36 pm
SJU
-
PWM
10h 56m2 stops
American Airlines Logo
6:01 am - 7:45 pm
PWM
-
SJU
13h 44m2 stops
$581American Airlines
Fri, May 1 - Sat, May 16

American Airlines flights from Caribbean to Portland, Maine

Our best American Airlines deals on Caribbean to Portland, Maine flight tickets
American Airlines
Feb 4
SJU6:00 amSan Juan Luis Munoz Marin Intl
10h 31m
2 stops
PWM3:31 pmPortland
Feb 8
PWM6:00 amPortland
16h 56m
1 stop
SJU11:56 pmSan Juan Luis Munoz Marin Intl
$231
Find similar
American Airlines
Feb 4
SJU8:20 amSan Juan Luis Munoz Marin Intl
15h 34m
2 stops
PWM10:54 pmPortland
Feb 8
PWM5:20 amPortland
10h 43m
2 stops
SJU5:03 pmSan Juan Luis Munoz Marin Intl
$303
Find similar
American Airlines
May 1
SJU5:40 amSan Juan Luis Munoz Marin Intl
10h 56m
2 stops
PWM4:36 pmPortland
May 16
PWM6:01 amPortland
7h 51m
1 stop
SJU1:52 pmSan Juan Luis Munoz Marin Intl
$433
Find similar

United Airlines flights from Caribbean to Portland, Maine

Our best United Airlines deals on Caribbean to Portland, Maine flight tickets
United Airlines
Mar 2
SJU2:05 amSan Juan Luis Munoz Marin Intl
14h 09m
2 stops
PWM3:14 pmPortland
Mar 4
PWM6:00 amPortland
14h 00m
2 stops
SJU9:00 pmSan Juan Luis Munoz Marin Intl
$356
Find similar
United Airlines
Mar 2
SJU2:05 amSan Juan Luis Munoz Marin Intl
14h 09m
2 stops
PWM3:14 pmPortland
Mar 4
PWM6:00 amPortland
7h 40m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$399
Find similar
United Airlines
Mar 3
SJU8:10 amSan Juan Luis Munoz Marin Intl
7h 13m
1 stop
PWM2:23 pmPortland
Mar 4
PWM6:00 amPortland
7h 40m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$411
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Caribbean to Portland, Maine 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 18, 2025.
Use the filters below to find and compare flights from Caribbean to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/4

6:00 am-3:31 pm

2 stops10h 31m

Portland

Sun 2/8

6:00 am-11:56 pm

1 stop16h 56m

$231

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/4

8:20 am-10:54 pm

2 stops15h 34m

Portland

Sun 2/8

5:20 am-5:03 pm

2 stops10h 43m

$303

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 3/2

2:05 am-3:14 pm

2 stops14h 09m

Portland

Wed 3/4

6:00 am-2:40 pm

1 stop7h 40m

$356

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 3/3

8:10 am-2:23 pm

1 stop7h 13m

Portland

Wed 3/4

6:00 am-2:40 pm

1 stop7h 40m

$411

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 5/1

5:40 am-4:36 pm

2 stops10h 56m

Portland

Sat 5/16

6:01 am-1:52 pm

1 stop7h 51m

$433

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 3/3

8:10 am-2:23 pm

1 stop7h 13m

Portland

Wed 3/4

6:00 am-2:40 pm

1 stop7h 40m

$505

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 5/1

5:40 am-4:36 pm

2 stops10h 56m

Portland

Sat 5/16

6:01 am-7:45 pm

2 stops13h 44m

$581

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 12/25

8:10 am-6:51 pm

2 stops11h 41m

$106

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 12/25

7:00 am-12:20 pm

1 stop6h 20m

$138

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 12/24

10:15 am-11:22 pm

2 stops14h 07m

$151

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
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See travel insights to Boston from

How to get the cheapest flight ticket from Caribbean to Portland, Maine

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 Portland, Maine?

On average, the least expensive day to fly to Portland, Maine from Caribbean is on a Thursday. momondo users have found tickets for Thursday departures for as low as $505. However, this price may fluctuate depending on the airline, the season, and holidays. On the other hand, Tuesday is the most expensive day to depart from Caribbean because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $634.

What is the cheapest time of day to depart on your flight to Portland, Maine?

In the evening is the cheapest time of day to fly from Caribbean to Portland, Maine when you can find flight prices for as low as $336. Flying to Portland, Maine in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $548. Of course, these prices can vary depending on the time of year and what airport you fly to.

Can stopping save me money on Caribbean to Portland, Maine flights?

You could potentially save up to 56% on your flight if you consider stops on a Caribbean to Portland, Maine flight.

Cheap Caribbean to Portland, Maine flight deals and tips

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

Fastest flight time

7h 00m

Direct flights

None
The fastest flight from Caribbean to Portland, Maine takes 7h 00m
There are no direct flights from Caribbean to Portland, Maine. There are no popular flight routes from Caribbean to Portland, Maine.
Search flight deals

  • When did momondo last update prices for flights from Caribbean to Portland Airport?

    Prices for flights from Caribbean to Portland Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Caribbean to Portland Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Caribbean to Portland Airport.

  • What documentation or ID do you need to fly to Portland Airport?

    The travel and health documents you'll need for your trip to Portland 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 Portland Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Caribbean to Portland, Maine

Compare and see reviews for airlines that fly from Caribbean to Portland, Maine with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $370Free CancellationRating
7.2
11,054 reviews
Search American Airlines flights
United AirlinesPriceFrom $383Free CancellationRating
7.4
9,091 reviews
Search United Airlines flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Bartlett
Brunswick
Auburn
Gorham
Windham
Intervale
Oxford
Bath
Georgetown
Falmouth
Tamworth

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Caribbean to Portland for you.

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

momondo does allow users to show only those flights to Portland from Caribbean which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Caribbean to Portland?

Once you have performed a search for Caribbean to Portland flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Portland from Caribbean. 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.

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