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Cheap flights from Caribbean to Portland from $239

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 Portland departing on 7/29. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Caribbean to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:30 am - 6:13 pm
SJU
-
PWM
10h 43m
2 stops
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m
1 stop
$308United Airlines
Wed, Oct 28 - Mon, Nov 2
Delta Logo
5:50 pm - 12:59 am
SJU
-
PWM
7h 09m
1 stop
Delta Logo
6:05 am - 4:38 pm
PWM
-
SJU
10h 33m
1 stop
$312Delta
Fri, Aug 21 - Sat, Aug 29
Southwest Logo
5:35 am - 4:05 pm
SJU
-
PWM
10h 30m
2 stops
Southwest Logo
5:20 am - 5:00 pm
PWM
-
SJU
10h 40m
2 stops
$332Southwest
Wed, Oct 28 - Mon, Nov 2
American Airlines Logo
7:30 am - 10:00 pm
SJU
-
PWM
14h 30m
1 stop
American Airlines Logo
7:28 am - 4:57 pm
PWM
-
SJU
9h 29m
2 stops
$337American Airlines
Fri, Aug 21 - Sat, Aug 29
American Airlines Logo
7:30 am - 10:00 pm
SJU
-
PWM
14h 30m
1 stop
American Airlines Logo
6:00 am - 4:57 pm
PWM
-
SJU
10h 57m
2 stops
$347American Airlines
Fri, Aug 21 - Sat, Aug 29
United Airlines Logo
1:25 pm - 11:59 pm
SJU
-
PWM
10h 34m
2 stops
United Airlines Logo
6:00 am - 2:44 pm
PWM
-
SJU
8h 44m
1 stop
$348United Airlines
Fri, Oct 23 - Sat, Oct 24
United Airlines Logo
4:55 pm - 11:59 pm
SJU
-
PWM
7h 04m
1 stop
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
$402United Airlines
Fri, Oct 23 - Sat, Oct 24
JetBlue Logo
5:01 am - 1:45 pm
SJU
-
PWM
8h 44m
1 stop
JetBlue Logo
6:00 am - 1:34 pm
PWM
-
SJU
7h 34m
1 stop
$408JetBlue
Wed, Sep 2 - Wed, Sep 23
Southwest Logo
6:00 am - 3:00 pm
SJU
-
PWM
9h 00m
2 stops
Southwest Logo
7:25 am - 6:05 pm
PWM
-
SJU
10h 40m
2 stops
$413Southwest
Fri, Aug 21 - Sat, Aug 29
American Airlines Logo
6:00 am - 11:24 pm
SJU
-
PWM
17h 24m
1 stop
American Airlines Logo
6:00 am - 11:41 pm
PWM
-
SJU
17h 41m
1 stop
$417American Airlines
Fri, Oct 16 - Sun, Oct 18

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American Airlines flights from Caribbean to Portland, Maine

Our best American Airlines deals on Caribbean to Portland, Maine flight tickets
American Airlines
Aug 21
SJU7:30 amSan Juan Luis Munoz Marin Intl
14h 30m
1 stop
PWM10:00 pmPortland
Aug 29
PWM7:28 amPortland
9h 29m
2 stops
SJU4:57 pmSan Juan Luis Munoz Marin Intl
$337
American Airlines
Aug 21
SJU7:30 amSan Juan Luis Munoz Marin Intl
14h 30m
1 stop
PWM10:00 pmPortland
Aug 29
PWM6:00 amPortland
10h 57m
2 stops
SJU4:57 pmSan Juan Luis Munoz Marin Intl
$347
American Airlines
Oct 16
SJU6:00 amSan Juan Luis Munoz Marin Intl
17h 24m
1 stop
PWM11:24 pmPortland
Oct 18
PWM6:00 amPortland
17h 41m
1 stop
SJU11:41 pmSan Juan Luis Munoz Marin Intl
$417

United Airlines flights from Caribbean to Portland, Maine

Our best United Airlines deals on Caribbean to Portland, Maine flight tickets
United Airlines
Oct 28
SJU7:30 amSan Juan Luis Munoz Marin Intl
10h 43m
2 stops
PWM6:13 pmPortland
Nov 2
PWM6:00 amPortland
7h 40m
1 stop
SJU2:40 pmSan Juan Luis Munoz Marin Intl
$308
United Airlines
Oct 23
SJU1:25 pmSan Juan Luis Munoz Marin Intl
10h 34m
2 stops
PWM11:59 pmPortland
Oct 24
PWM6:00 amPortland
8h 44m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
$348
United Airlines
Oct 23
SJU4:55 pmSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
PWM11:59 pmPortland
Oct 24
PWM6:00 amPortland
7h 45m
1 stop
SJU1:45 pmSan Juan Luis Munoz Marin Intl
$402

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 June 16, 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

Cheapest round-trip

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 10/28

7:30 am-6:13 pm

2 stops10h 43m

Portland

Mon 11/2

6:00 am-2:40 pm

1 stop7h 40m

$308

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/21

5:50 pm-12:59 am

1 stop7h 09m

Portland

Sat 8/29

6:05 am-4:38 pm

1 stop10h 33m

$312

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 10/28

5:35 am-4:05 pm

2 stops10h 30m

Portland

Mon 11/2

5:20 am-5:00 pm

2 stops10h 40m

$332

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/21

7:30 am-10:00 pm

1 stop14h 30m

Portland

Sat 8/29

7:28 am-4:57 pm

2 stops9h 29m

$337

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/21

7:30 am-10:00 pm

1 stop14h 30m

Portland

Sat 8/29

6:00 am-4:57 pm

2 stops10h 57m

$347

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 10/23

1:25 pm-11:59 pm

2 stops10h 34m

Portland

Sat 10/24

6:00 am-2:44 pm

1 stop8h 44m

$348
Quickest round-trip

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 10/23

4:55 pm-11:59 pm

1 stop7h 04m

Portland

Sat 10/24

6:00 am-1:45 pm

1 stop7h 45m

$402

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 9/2

5:01 am-1:45 pm

1 stop8h 44m

Portland

Wed 9/23

6:00 am-1:34 pm

1 stop7h 34m

$408

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/21

6:00 am-3:00 pm

2 stops9h 00m

Portland

Sat 8/29

7:25 am-6:05 pm

2 stops10h 40m

$413

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 10/16

6:00 am-11:24 pm

1 stop17h 24m

Portland

Sun 10/18

6:00 am-11:41 pm

1 stop17h 41m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Portland 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 5% 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 04m

Direct flights

None
The fastest flight from Caribbean to Portland, Maine takes 7h 04m
There are no direct flights from Caribbean to Portland, Maine. There are no popular flight routes from Caribbean to Portland, Maine.
Search flight deals

Frequently asked questions about flying from Caribbean to Portland, Maine

  • 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 $474Free CancellationRating
7.1
11,666 reviews
Search American Airlines flights

Traveling to a place near Portland?

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