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Cheap flights from Caribbean to Portland from $151

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 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 Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:42 pm - 12:46 am
SJU
-
PWM
7h 04m
1 stop
Delta Logo
2:38 pm - 11:35 pm
PWM
-
SJU
8h 57m
1 stop
$302Delta
Wed, May 6 - Mon, May 11
Multiple Airlines Logo
3:03 am - 4:16 pm
SJU
-
PWM
13h 13m
2 stops
Multiple Airlines Logo
5:01 pm - 3:12 pm
PWM
-
SJU
22h 11m
1 stop
$320Multiple Airlines
Tue, May 5 - Sat, May 9
United Airlines Logo
4:55 pm - 11:59 pm
SJU
-
PWM
7h 04m
1 stop
United Airlines Logo
5:30 am - 8:38 pm
PWM
-
SJU
15h 08m
2 stops
$322United Airlines
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
5:15 pm - 4:16 pm
SJU
-
PWM
23h 01m
2 stops
Multiple Airlines Logo
5:01 pm - 3:12 pm
PWM
-
SJU
22h 11m
1 stop
$328Multiple Airlines
Tue, May 5 - Sat, May 9
United Airlines Logo
1:00 am - 10:18 am
SJU
-
PWM
9h 18m
2 stops
United Airlines Logo
9:40 am - 9:24 pm
PWM
-
SJU
11h 44m
2 stops
$332United Airlines
Mon, May 4 - Sat, May 9
United Airlines Logo
1:00 am - 8:49 am
SJU
-
PWM
7h 49m
1 stop
United Airlines Logo
2:08 pm - 9:24 pm
PWM
-
SJU
7h 16m
1 stop
$335United Airlines
Thu, Apr 30 - Thu, May 7
American Airlines Logo
11:43 am - 11:54 pm
SJU
-
PWM
12h 11m
2 stops
American Airlines Logo
6:00 am - 10:05 pm
PWM
-
SJU
16h 05m
1 stop
$347American Airlines
Tue, May 5 - Tue, May 12
Multiple Airlines Logo
7:00 am - 7:16 pm
SJU
-
PWM
12h 16m
2 stops
Multiple Airlines Logo
5:01 pm - 3:12 pm
PWM
-
SJU
22h 11m
1 stop
$350Multiple Airlines
Thu, May 7 - Sat, May 9
United Airlines Logo
1:00 am - 2:14 pm
SJU
-
PWM
13h 14m
2 stops
United Airlines Logo
2:08 pm - 9:24 pm
PWM
-
SJU
7h 16m
1 stop
$355United Airlines
Thu, Apr 30 - Thu, May 7
United Airlines Logo
1:00 am - 10:18 am
SJU
-
PWM
9h 18m
2 stops
United Airlines Logo
5:30 am - 12:34 pm
PWM
-
SJU
7h 04m
1 stop
$363United Airlines
Wed, May 6 - Sun, May 10

Delta flights from Caribbean to Portland, Maine

Our best Delta deals on Caribbean to Portland, Maine flight tickets
Delta
May 6
SJU5:42 pmSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
PWM12:46 amPortland
May 12
PWM2:05 pmPortland
8h 12m
1 stop
SJU10:17 pmSan Juan Luis Munoz Marin Intl
$302
Delta
Jun 12
SJU5:45 pmSan Juan Luis Munoz Marin Intl
7h 07m
1 stop
PWM12:52 amPortland
Jul 5
PWM6:20 amPortland
10h 07m
1 stop
SJU4:27 pmSan Juan Luis Munoz Marin Intl
$370
Delta
May 3
SJU12:55 pmSan Juan Luis Munoz Marin Intl
10h 28m
1 stop
PWM11:23 pmPortland
May 12
PWM2:05 pmPortland
8h 12m
1 stop
SJU10:17 pmSan Juan Luis Munoz Marin Intl
$554

United Airlines flights from Caribbean to Portland, Maine

Our best United Airlines deals on Caribbean to Portland, Maine flight tickets
United Airlines
May 2
SJU4:55 pmSan Juan Luis Munoz Marin Intl
7h 04m
1 stop
PWM11:59 pmPortland
May 9
PWM5:30 amPortland
15h 08m
2 stops
SJU8:38 pmSan Juan Luis Munoz Marin Intl
$322
United Airlines
May 4
SJU1:00 amSan Juan Luis Munoz Marin Intl
9h 18m
2 stops
PWM10:18 amPortland
May 9
PWM9:40 amPortland
11h 44m
2 stops
SJU9:24 pmSan Juan Luis Munoz Marin Intl
$332
United Airlines
Apr 30
SJU1:00 amSan Juan Luis Munoz Marin Intl
7h 49m
1 stop
PWM8:49 amPortland
May 7
PWM2:08 pmPortland
7h 16m
1 stop
SJU9:24 pmSan Juan Luis Munoz Marin Intl
$335

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 April 21, 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 5/6

5:42 pm-12:46 am

1 stop7h 04m

Portland

Mon 5/11

2:38 pm-11:35 pm

1 stop8h 57m

$302

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/5

3:03 am-4:16 pm

2 stops13h 13m

Portland

Sat 5/9

5:01 pm-3:12 pm

1 stop22h 11m

$320

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 5/2

4:55 pm-11:59 pm

1 stop7h 04m

Portland

Sat 5/9

5:30 am-8:38 pm

2 stops15h 08m

$322

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/5

5:15 pm-4:16 pm

2 stops23h 01m

Portland

Sat 5/9

5:01 pm-3:12 pm

1 stop22h 11m

$328

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 5/4

1:00 am-10:18 am

2 stops9h 18m

Portland

Sat 5/9

9:40 am-9:24 pm

2 stops11h 44m

$332
Quickest round-trip

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-8:49 am

1 stop7h 49m

Portland

Thu 5/7

2:08 pm-9:24 pm

1 stop7h 16m

$335

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 5/5

11:43 am-11:54 pm

2 stops12h 11m

Portland

Tue 5/12

6:00 am-10:05 pm

1 stop16h 05m

$347

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 5/7

7:00 am-7:16 pm

2 stops12h 16m

Portland

Sat 5/9

5:01 pm-3:12 pm

1 stop22h 11m

$350

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Thu 4/30

1:00 am-2:14 pm

2 stops13h 14m

Portland

Thu 5/7

2:08 pm-9:24 pm

1 stop7h 16m

$355

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 5/6

1:00 am-10:18 am

2 stops9h 18m

Portland

Sun 5/10

5:30 am-12:34 pm

1 stop7h 04m

$363

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 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 32% 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 07m

Direct flights

None
The fastest flight from Caribbean to Portland, Maine takes 7h 07m
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 $441Free CancellationRating
7.1
11,645 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
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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