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Cheap flights from Caribbean to Boston from $138

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 10/27. 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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Cheap round-trip flights

American Airlines Logo
6:50 pm - 12:09 pmSJU-PWM
18h 19m2 stops
American Airlines Logo
5:15 pm - 1:35 pmPWM-SJU
19h 20m2 stops
$295American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
5:30 am - 3:35 pmSJU-PWM
10h 05m1 stop
American Airlines Logo
5:00 am - 10:52 pmPWM-SJU
16h 52m1 stop
$303American Airlines
Find Deal
Mon, Oct 27 - Sun, Nov 2
JetBlue Logo
6:00 am - 2:26 pmSJU-PWM
9h 26m1 stop
JetBlue Logo
3:25 pm - 12:50 amPWM-SJU
8h 25m1 stop
$374JetBlue
Find Deal
Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
1:50 pm - 11:51 pmSJU-PWM
10h 01m2 stops
American Airlines Logo
5:00 am - 10:52 pmPWM-SJU
16h 52m1 stop
$380American Airlines
Find Deal
Mon, Oct 27 - Sun, Nov 2
American Airlines Logo
6:40 am - 1:53 pmSJU-PWM
8h 13m2 stops
American Airlines Logo
5:15 pm - 11:20 pmPWM-SJU
29h 05m2 stops
$388American Airlines
Find Deal
Wed, Feb 18 - Sat, Feb 21
Delta Logo
7:00 am - 1:58 pmSJU-PWM
6h 58m1 stop
Delta Logo
6:50 am - 4:25 pmPWM-SJU
9h 35m1 stop
$406Delta
Find Deal
Mon, Oct 20 - Mon, Oct 27
Southwest Logo
10:05 am - 12:05 amSJU-PWM
14h 00m2 stops
Southwest Logo
5:30 am - 7:50 pmPWM-SJU
13h 20m2 stops
$515Southwest
Find Deal
Mon, Oct 27 - Sun, Nov 2
Southwest Logo
6:15 am - 12:05 pmSJU-PWM
6h 50m1 stop
Southwest Logo
5:25 pm - 1:35 amPWM-SJU
7h 10m1 stop
$620Southwest
Find Deal
Thu, Nov 27 - Sun, Nov 30
United Airlines Logo
1:05 am - 9:11 amSJU-PWM
8h 06m1 stop
United Airlines Logo
6:00 am - 1:40 pmPWM-SJU
7h 40m1 stop
$630United Airlines
Find Deal
Sun, Oct 19 - Mon, Oct 27
United Airlines Logo
1:05 am - 9:18 amSJU-PWM
8h 13m1 stop
United Airlines Logo
5:00 am - 1:40 pmPWM-SJU
7h 40m1 stop
$710United Airlines
Find Deal
Sun, Oct 26 - Sun, Nov 2

United Airlines flights from Caribbean to Portland, Maine

Our best United Airlines deals on Caribbean to Portland, Maine flight tickets
United Airlines
Oct 19
SJU1:05 amSan Juan Luis Munoz Marin Intl
8h 06m
1 stop
PWM9:11 amPortland
Oct 27
PWM6:00 amPortland
7h 40m
1 stop
SJU1:40 pmSan Juan Luis Munoz Marin Intl
$630
Find similar
United Airlines
Oct 26
SJU1:05 amSan Juan Luis Munoz Marin Intl
8h 13m
1 stop
PWM9:18 amPortland
Nov 2
PWM5:00 amPortland
7h 40m
1 stop
SJU1:40 pmSan Juan Luis Munoz Marin Intl
$710
Find similar
United Airlines
Nov 26
SJU2:05 amSan Juan Luis Munoz Marin Intl
13h 07m
2 stops
PWM2:12 pmPortland
Nov 30
PWM6:00 amPortland
7h 40m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$793
Find similar

American Airlines flights from Caribbean to Portland, Maine

Our best American Airlines deals on Caribbean to Portland, Maine flight tickets
American Airlines
Feb 18
SJU6:50 pmSan Juan Luis Munoz Marin Intl
18h 19m
2 stops
PWM12:09 pmPortland
Feb 21
PWM5:15 pmPortland
19h 20m
2 stops
SJU1:35 pmSan Juan Luis Munoz Marin Intl
$295
Find similar
American Airlines
Oct 27
SJU5:30 amSan Juan Luis Munoz Marin Intl
10h 05m
1 stop
PWM3:35 pmPortland
Nov 2
PWM5:00 amPortland
16h 52m
1 stop
SJU10:52 pmSan Juan Luis Munoz Marin Intl
$303
Find similar
American Airlines
Oct 27
SJU1:50 pmSan Juan Luis Munoz Marin Intl
10h 01m
2 stops
PWM11:51 pmPortland
Nov 2
PWM5:00 amPortland
16h 52m
1 stop
SJU10:52 pmSan Juan Luis Munoz Marin Intl
$380
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 September 25, 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 2/18

6:50 pm-12:09 pm

2 stops18h 19m

Portland

Sat 2/21

5:15 pm-1:35 pm

2 stops19h 20m

$295

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 10/27

5:30 am-3:35 pm

1 stop10h 05m

Portland

Sun 11/2

5:00 am-10:52 pm

1 stop16h 52m

$303

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/18

6:00 am-2:26 pm

1 stop9h 26m

Portland

Sat 2/21

3:25 pm-12:50 am

1 stop8h 25m

$374

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 10/27

1:50 pm-11:51 pm

2 stops10h 01m

Portland

Sun 11/2

5:00 am-10:52 pm

1 stop16h 52m

$380

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 2/18

6:40 am-1:53 pm

2 stops8h 13m

Portland

Sat 2/21

5:15 pm-11:20 pm

2 stops29h 05m

$388

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 10/20

7:00 am-1:58 pm

1 stop6h 58m

Portland

Mon 10/27

6:50 am-4:25 pm

1 stop9h 35m

$406

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 10/27

10:05 am-12:05 am

2 stops14h 00m

Portland

Sun 11/2

5:30 am-7:50 pm

2 stops13h 20m

$515

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 11/27

6:15 am-12:05 pm

1 stop6h 50m

Portland

Sun 11/30

5:25 pm-1:35 am

1 stop7h 10m

$620

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 10/19

1:05 am-9:11 am

1 stop8h 06m

Portland

Mon 10/27

6:00 am-1:40 pm

1 stop7h 40m

$630

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 10/26

1:05 am-9:18 am

1 stop8h 13m

Portland

Sun 11/2

5:00 am-1:40 pm

1 stop7h 40m

$710

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 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 55% 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

Direct flights

None
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
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $383Free CancellationRating
7.4
8,928 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
Gorham
Auburn
Intervale
Windham
Bath
Oxford
Georgetown
Tamworth
Falmouth

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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