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Cheap flights from Caribbean to Boston from $121

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 5/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Caribbean to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
4:25 pm - 11:25 pm
SJU
-
PWM
7h 00m
1 stop
Southwest Logo
5:30 am - 12:10 pm
PWM
-
SJU
6h 40m
1 stop
$385Southwest
Fri, May 22 - Mon, May 25
Southwest Logo
5:35 am - 12:10 pm
SJU
-
PWM
6h 35m
1 stop
Southwest Logo
5:30 am - 2:55 pm
PWM
-
SJU
9h 25m
2 stops
$387Southwest
Thu, May 21 - Mon, May 25
Southwest Logo
5:35 am - 12:10 pm
SJU
-
PWM
6h 35m
1 stop
Southwest Logo
5:30 am - 12:10 pm
PWM
-
SJU
6h 40m
1 stop
$406Southwest
Thu, May 21 - Mon, May 25
Southwest Logo
5:05 am - 2:10 pm
SJU
-
PWM
9h 05m
2 stops
Southwest Logo
5:30 am - 2:55 pm
PWM
-
SJU
9h 25m
2 stops
$438Southwest
Thu, May 21 - Mon, May 25
JetBlue Logo
3:05 am - 1:24 pm
SJU
-
PWM
10h 19m
1 stop
JetBlue Logo
6:00 am - 10:47 pm
PWM
-
SJU
16h 47m
1 stop
$455JetBlue
Thu, Jun 4 - Sun, Jun 7
Southwest Logo
1:15 pm - 12:05 am
SJU
-
PWM
10h 50m
2 stops
Southwest Logo
5:30 am - 12:25 pm
PWM
-
SJU
6h 55m
1 stop
$457Southwest
Fri, Jun 5 - Sun, Jun 7
JetBlue Logo
7:00 am - 1:50 pm
SJU
-
PWM
6h 50m
1 stop
JetBlue Logo
2:30 pm - 11:59 pm
PWM
-
SJU
9h 29m
1 stop
$496JetBlue
Fri, Mar 13 - Mon, Mar 16
Multiple Airlines Logo
6:30 am - 10:17 am
SJU
-
PWM
27h 47m
1 stop
Multiple Airlines Logo
11:29 am - 12:29 am
PWM
-
SJU
37h 00m
2 stops
$521Multiple Airlines
Fri, Mar 13 - Mon, Mar 16
Southwest Logo
1:15 pm - 12:05 am
SJU
-
PWM
10h 50m
2 stops
Southwest Logo
5:30 am - 3:25 pm
PWM
-
SJU
9h 55m
2 stops
$557Southwest
Fri, Jun 5 - Sun, Jun 7
American Airlines Logo
7:20 am - 10:40 pm
SJU
-
PWM
15h 20m
1 stop
American Airlines Logo
7:23 am - 12:17 am
PWM
-
SJU
16h 54m
1 stop
$579American Airlines
Fri, Jul 10 - Sun, Jul 12

Southwest flights from Caribbean to Portland, Maine

Our best Southwest deals on Caribbean to Portland, Maine flight tickets
Southwest
May 22
SJU4:25 pmSan Juan Luis Munoz Marin Intl
7h 00m
1 stop
PWM11:25 pmPortland
May 25
PWM5:30 amPortland
9h 25m
2 stops
SJU2:55 pmSan Juan Luis Munoz Marin Intl
$385
Southwest
May 21
SJU5:35 amSan Juan Luis Munoz Marin Intl
6h 35m
1 stop
PWM12:10 pmPortland
May 25
PWM5:30 amPortland
9h 25m
2 stops
SJU2:55 pmSan Juan Luis Munoz Marin Intl
$387
Southwest
May 22
SJU4:25 pmSan Juan Luis Munoz Marin Intl
7h 00m
1 stop
PWM11:25 pmPortland
May 25
PWM5:30 amPortland
6h 40m
1 stop
SJU12:10 pmSan Juan Luis Munoz Marin Intl
$394

JetBlue flights from Caribbean to Portland, Maine

Our best JetBlue deals on Caribbean to Portland, Maine flight tickets
JetBlue
Jun 4
SJU3:05 amSan Juan Luis Munoz Marin Intl
10h 19m
1 stop
PWM1:24 pmPortland
Jun 7
PWM6:00 amPortland
16h 47m
1 stop
SJU10:47 pmSan Juan Luis Munoz Marin Intl
$455
JetBlue
Mar 13
SJU7:00 amSan Juan Luis Munoz Marin Intl
6h 50m
1 stop
PWM1:50 pmPortland
Mar 16
PWM2:30 pmPortland
9h 29m
1 stop
SJU11:59 pmSan Juan Luis Munoz Marin Intl
$496

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 March 2, 2026.
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

Fri 5/22

4:25 pm-11:25 pm

1 stop7h 00m

Portland

Mon 5/25

5:30 am-12:10 pm

1 stop6h 40m

$385

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 5/21

5:35 am-12:10 pm

1 stop6h 35m

Portland

Mon 5/25

5:30 am-2:55 pm

2 stops9h 25m

$387

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 5/21

5:35 am-12:10 pm

1 stop6h 35m

Portland

Mon 5/25

5:30 am-12:10 pm

1 stop6h 40m

$406

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 5/21

5:05 am-2:10 pm

2 stops9h 05m

Portland

Mon 5/25

5:30 am-2:55 pm

2 stops9h 25m

$438

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 6/4

3:05 am-1:24 pm

1 stop10h 19m

Portland

Sun 6/7

6:00 am-10:47 pm

1 stop16h 47m

$455

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 6/5

1:15 pm-12:05 am

2 stops10h 50m

Portland

Sun 6/7

5:30 am-12:25 pm

1 stop6h 55m

$457

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 3/13

7:00 am-1:50 pm

1 stop6h 50m

Portland

Mon 3/16

2:30 pm-11:59 pm

1 stop9h 29m

$496

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 3/13

6:30 am-10:17 am

1 stop27h 47m

Portland

Mon 3/16

11:29 am-12:29 am

2 stops37h 00m

$521

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 6/5

1:15 pm-12:05 am

2 stops10h 50m

Portland

Sun 6/7

5:30 am-3:25 pm

2 stops9h 55m

$557

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 7/10

7:20 am-10:40 pm

1 stop15h 20m

Portland

Sun 7/12

7:23 am-12:17 am

1 stop16h 54m

$579

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

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

You could potentially save up to 51% 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

6h 56m

Direct flights

None
The fastest flight from Caribbean to Portland, Maine takes 6h 56m
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
7.1
11,369 reviews
Search American 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
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
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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