What airlines fly to Caribbean?

JetBlue, Delta and American Airlines are the top three most popular airlines that fly to Caribbean from Portland, Maine according to our data. JetBlue is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 11 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Portland to Caribbean?

American Airlines, United Airlines, and Delta are the most popular carriers operating from Portland to Caribbean

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

Prices for flights from Portland Airport to Caribbean were last updated today.

How many operators does momondo search for flights from Portland Airport to Caribbean?

There are 5 operators available for flights from Portland Airport to Caribbean as of February 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean.

What documentation or ID do you need to fly to Caribbean?

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

$102 Cheap Flights from Portland to Caribbean in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Portland, Maine to Caribbean

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:39 am - 8:34 pm

PWM

SJU

10h 55m

1 stop

1:00 am - 8:49 am

SJU

PWM

7h 49m

1 stop

$212United Airlines

Fri, May 8 - Mon, May 11

6:36 pm - 2:03 pm

PWM

STT

18h 27m

2 stops

3:08 pm - 10:59 pm

STT

PWM

8h 51m

1 stop

$214American Airlines

Tue, Feb 24 - Tue, Mar 3

9:39 am - 8:34 pm

PWM

SJU

10h 55m

1 stop

1:00 am - 10:18 am

SJU

PWM

9h 18m

2 stops

$220United Airlines

Fri, May 8 - Mon, May 11

5:31 am - 3:04 pm

PWM

STT

8h 33m

1 stop

5:32 pm - 12:18 am

STT

PWM

7h 46m

1 stop

$270Delta

Tue, Feb 24 - Tue, Mar 3

6:18 am - 4:50 pm

PWM

SJU

9h 32m

1 stop

1:17 pm - 11:03 pm

SJU

PWM

9h 46m

1 stop

$276Delta

Tue, Feb 24 - Wed, Mar 11

6:36 pm - 9:34 pm

PWM

SJU

25h 58m

2 stops

2:23 pm - 11:59 am

SJU

PWM

22h 36m

2 stops

$292American Airlines

Mon, Feb 23 - Tue, Mar 3

2:25 pm - 1:05 am

PWM

SJU

9h 40m

1 stop

6:30 am - 1:45 pm

SJU

PWM

8h 15m

1 stop

$300Southwest

Sun, Feb 22 - Fri, Feb 27

4:30 pm - 11:55 pm

PWM

SJU

6h 25m

1 stop

6:10 am - 2:50 pm

SJU

PWM

9h 40m

1 stop

$315Southwest

Sat, Feb 28 - Wed, Mar 4

6:00 am - 1:03 pm

PWM

PLS

7h 03m

1 stop

2:24 pm - 11:36 pm

PLS

PWM

9h 12m

1 stop

$335JetBlue

Fri, May 15 - Tue, May 19

6:00 am - 11:55 am

PWM

NAS

5h 55m

1 stop

7:55 am - 3:30 pm

NAS

PWM

7h 35m

1 stop

$393JetBlue

Tue, Mar 31 - Sat, Apr 4

Delta flights from Portland, Maine to Caribbean

Our best Delta deals on Portland, Maine to Caribbean flight tickets

Delta

Feb 24

PWM5:31 amPortland

8h 33m

1 stop

STT3:04 pmSaint Thomas Island Cyril E King

Mar 3

STT5:32 pmSaint Thomas Island Cyril E King

7h 46m

1 stop

PWM12:18 amPortland

$270

Delta

Feb 24

PWM6:18 amPortland

9h 32m

1 stop

SJU4:50 pmSan Juan Luis Munoz Marin Intl

Mar 5

SJU6:02 pmSan Juan Luis Munoz Marin Intl

7h 16m

1 stop

PWM12:18 amPortland

$276

Delta

Feb 22

PWM5:31 amPortland

9h 51m

1 stop

STT4:22 pmSaint Thomas Island Cyril E King

Feb 26

STT3:10 pmSaint Thomas Island Cyril E King

8h 56m

1 stop

PWM11:06 pmPortland

$278

American Airlines flights from Portland, Maine to Caribbean

Our best American Airlines deals on Portland, Maine to Caribbean flight tickets

American Airlines

Feb 24

PWM6:36 pmPortland

20h 11m

2 stops

STT3:47 pmSaint Thomas Island Cyril E King

Mar 3

STT3:08 pmSaint Thomas Island Cyril E King

8h 51m

1 stop

PWM10:59 pmPortland

$214

American Airlines

Feb 23

PWM6:36 pmPortland

25h 58m

2 stops

SJU9:34 pmSan Juan Luis Munoz Marin Intl

Mar 3

SJU2:23 pmSan Juan Luis Munoz Marin Intl

22h 36m

2 stops

PWM11:59 amPortland

$292

American Airlines

Feb 24

PWM6:36 pmPortland

17h 57m

2 stops

SJU1:33 pmSan Juan Luis Munoz Marin Intl

Mar 11

SJU11:30 amSan Juan Luis Munoz Marin Intl

11h 20m

1 stop

PWM10:50 pmPortland

$297

momondo Fare Finder

Use the filters below to find and compare flights from Portland, Maine to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 5/8

9:39 am-8:34 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Mon 5/11

1:00 am-8:49 am

1 stop7h 49m

$212

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 2/24

6:36 pm-2:03 pm

2 stops18h 27m

Saint Thomas Island Cyril E King

Tue 3/3

3:08 pm-10:59 pm

1 stop8h 51m

$214

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Fri 5/8

9:39 am-8:34 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Mon 5/11

1:00 am-10:18 am

2 stops9h 18m

$220

PortlandSaint Thomas Island

PWM - STT

PWMSTT

Portland

Tue 2/24

5:31 am-3:04 pm

1 stop8h 33m

Saint Thomas Island Cyril E King

Tue 3/3

5:32 pm-12:18 am

1 stop7h 46m

$270

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Tue 2/24

6:18 am-4:50 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Wed 3/11

1:17 pm-11:03 pm

1 stop9h 46m

$276

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Mon 2/23

6:36 pm-9:34 pm

2 stops25h 58m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:23 pm-11:59 am

2 stops22h 36m

$292

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sun 2/22

2:25 pm-1:05 am

1 stop9h 40m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:30 am-1:45 pm

1 stop8h 15m

$300

PortlandSan Juan

PWM - SJU

PWMSJU

Portland

Sat 2/28

4:30 pm-11:55 pm

1 stop6h 25m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:10 am-2:50 pm

1 stop9h 40m

$315

PortlandProvidenciales

PWM - PLS

PWMPLS

Portland

Fri 5/15

6:00 am-1:03 pm

1 stop7h 03m

Providenciales

Tue 5/19

2:24 pm-11:36 pm

1 stop9h 12m

$335

PortlandNassau

PWM - NAS

PWMNAS

Portland

Tue 3/31

6:00 am-11:55 am

1 stop5h 55m

Nassau Intl

Sat 4/4

7:55 am-3:30 pm

1 stop7h 35m

$393

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

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

Prices

Airlines

What is the cheapest month to fly to Caribbean?

In general, November is the cheapest month to fly from Portland, Maine to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $322. If you don’t want to visit Caribbean in November, then you should wait until October to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $343.

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Portland, Maine when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $455 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Portland, Maine for as low as $234 on momondo.

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

You could potentially save up to 17% on your flight if you consider stops on a Portland, Maine to Caribbean flight.

Cheap Portland, Maine to Caribbean flight deals and tips

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

Fastest flight time	5h 55m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean takes 5h 55m

There are no direct flights from Portland, Maine to Caribbean. There are no popular flight routes from Portland, Maine to Caribbean.

Search flight deals

When did momondo last update prices for flights from Portland Airport to Caribbean?
Prices for flights from Portland Airport to Caribbean were last updated today.
How many operators does momondo search for flights from Portland Airport to Caribbean?
There are 5 operators available for flights from Portland Airport to Caribbean as of February 2026.
How old do you have to be to fly from Portland Airport to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Portland Airport to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents you'll need for your trip to Caribbean 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 Caribbean. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Best airlines flying from Portland, Maine to Caribbean

Compare and see reviews for airlines that fly from Portland, Maine to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $113	Free Cancellation	Rating 7.9 8,132 reviews	Search Delta flights
JetBlue	PriceFrom $190	Free Cancellation	Rating 7.2 2,892 reviews	Search JetBlue flights
United Airlines	PriceFrom $241	Free Cancellation	Rating 7.4 9,231 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.2 11,212 reviews	Search American Airlines flights
Southwest	PriceFrom $315	Free Cancellation	Rating 8.0 4,271 reviews	Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Portland to Caribbean. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Portland to Caribbean on momondo can be filtered to show those which offer flexible booking policies.

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

Once all potential Portland to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Yes. momondo can track prices for Portland to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.