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

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 68% 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.

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 August 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.

$104 Cheap Flights from Portland, Maine to Caribbean in 2026

Discover deals from 900+ travel sites with momondo.

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.

4:54 pm - 12:58 pmPWM Portland-STT Saint Thomas Island Cyril E King

20h 04m2 stops Philadelphia Miami

1:48 pm - 11:06 amSTT Saint Thomas Island Cyril E King-PWM Portland

21h 18m2 stops Miami New York LaGuardia

$200American Airlines

Sat, Oct 24 - Thu, Oct 29

4:40 pm - 12:58 pmPWM Portland-STT Saint Thomas Island Cyril E King

20h 18m2 stops Philadelphia Miami

3:15 pm - 10:37 amSTT Saint Thomas Island Cyril E King-PWM Portland

20h 22m2 stops Miami Philadelphia

$200American Airlines

Thu, Oct 29 - Mon, Nov 2

6:00 am - 1:33 pmPWM Portland-NAS Nassau Intl

7h 33m1 stop Newark

2:35 pm - 11:28 pmNAS Nassau Intl-PWM Portland

8h 53m1 stop Newark

$321United Airlines

Mon, Oct 19 - Thu, Oct 22

4:20 pm - 11:49 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

7h 29m1 stop New York John F Kennedy Intl

1:16 pm - 11:56 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 40m1 stop New York John F Kennedy Intl

$346Delta

Wed, Sep 16 - Wed, Sep 23

12:45 pm - 11:20 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

9h 35m1 stop Baltimore/Washington

6:40 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 05m1 stop Baltimore/Washington

$346Southwest

Wed, Nov 11 - Wed, Nov 18

10:25 am - 10:20 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 55m2 stops Baltimore/Washington Tampa

6:10 am - 2:45 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

9h 35m2 stops Tampa Baltimore/Washington

$346Southwest

Wed, Nov 11 - Wed, Nov 18

6:00 am - 8:38 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

14h 38m2 stops Chicago O'Hare Intl Houston George Bush Intcntl

1:00 am - 9:08 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 08m1 stop Newark

$347United Airlines

Sat, Sep 19 - Sat, Sep 19

6:01 am - 4:49 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

10h 48m1 stop Atlanta Hartsfield-Jackson

1:15 pm - 12:10 amSJU San Juan Luis Munoz Marin Intl-PWM Portland

10h 55m1 stop New York John F Kennedy Intl

$352Delta

Tue, Oct 20 - Sat, Oct 24

7:00 am - 4:45 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

33h 45m2 stops Cincinnati Cinci./N. Kentucky Tampa

9:30 am - 5:51 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 21m1 stop Tampa

$391Multiple Airlines

Mon, Sep 28 - Sat, Oct 3

7:00 am - 4:45 pmPWM Portland-SJU San Juan Luis Munoz Marin Intl

33h 45m2 stops Cincinnati Cinci./N. Kentucky Tampa

9:30 am - 5:51 pmSJU San Juan Luis Munoz Marin Intl-PWM Portland

8h 21m1 stop Tampa

$392Multiple Airlines

Mon, Sep 28 - Sat, Oct 3

Cheap last minute flights

Enter your travel dates to find the best prices.

6:46 pm - 10:55 amPWM Portland-GCM George Town Owen Roberts Intl

17h 09m2 stops Philadelphia Miami

12:30 pm - 10:00 pmGCM George Town Owen Roberts Intl-PWM Portland

8h 30m1 stop Charlotte Douglas

$502American Airlines

Fri, Aug 14 - Wed, Aug 19

6:46 pm - 10:55 amPWM Portland-GCM George Town Owen Roberts Intl

17h 09m2 stops Philadelphia Miami

12:00 pm - 11:47 pmGCM George Town Owen Roberts Intl-PWM Portland

10h 47m2 stops Miami Washington, D.C. Reagan-National

$502American Airlines

Fri, Aug 14 - Wed, Aug 19

6:03 am - 12:40 pmPWM Portland-AUA Oranjestad Reina Beatrix

30h 37m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

4:30 pm - 5:42 pmAUA Oranjestad Reina Beatrix-PWM Portland

25h 12m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$754United Airlines

Sat, Aug 15 - Thu, Aug 20

6:03 am - 3:20 pmPWM Portland-AUA Oranjestad Reina Beatrix

9h 17m1 stop Chicago O'Hare Intl

4:30 pm - 9:23 pmAUA Oranjestad Reina Beatrix-PWM Portland

28h 53m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$754United Airlines

Sat, Aug 15 - Thu, Aug 20

6:05 am - 11:39 amPWM Portland-GCM George Town Owen Roberts Intl

6h 34m1 stop Atlanta Hartsfield-Jackson

1:04 pm - 11:13 pmGCM George Town Owen Roberts Intl-PWM Portland

9h 09m1 stop Atlanta Hartsfield-Jackson

$886Delta

Sat, Aug 15 - Mon, Aug 17

6:05 am - 11:39 amPWM Portland-GCM George Town Owen Roberts Intl

6h 34m1 stop Atlanta Hartsfield-Jackson

1:04 pm - 11:13 pmGCM George Town Owen Roberts Intl-PWM Portland

9h 09m1 stop Atlanta Hartsfield-Jackson

$886Delta

Fri, Aug 14 - Mon, Aug 17

6:38 pm - 5:20 pmPWM Portland-GCM George Town Owen Roberts Intl

23h 42m1 stop Tampa

12:40 pm - 10:38 pmGCM George Town Owen Roberts Intl-PWM Portland

32h 58m2 stops Tampa Cincinnati Cinci./N. Kentucky

$1,379Multiple Airlines

Sat, Aug 15 - Thu, Aug 20

6:00 am - 3:09 pmPWM Portland-STT Saint Thomas Island Cyril E King

33h 09m2 stops New York John F Kennedy Intl San Juan Luis Munoz Marin Intl

3:45 pm - 1:45 pmSTT Saint Thomas Island Cyril E King-PWM Portland

22h 00m2 stops San Juan Luis Munoz Marin Intl New York John F Kennedy Intl

$1,531JetBlue

Thu, Aug 13 - Wed, Aug 19

6:00 am - 3:09 pmPWM Portland-STT Saint Thomas Island Cyril E King

33h 09m2 stops New York John F Kennedy Intl San Juan Luis Munoz Marin Intl

3:45 pm - 1:45 pmSTT Saint Thomas Island Cyril E King-PWM Portland

22h 00m2 stops San Juan Luis Munoz Marin Intl New York John F Kennedy Intl

$1,731JetBlue

Thu, Aug 13 - Wed, Aug 19

11:50 am - 2:15 pmPWM Portland-AUA Oranjestad Reina Beatrix

50h 25m2 stops Minneapolis St Paul Toronto Pearson Intl

3:05 pm - 11:30 pmAUA Oranjestad Reina Beatrix-PWM Portland

32h 25m2 stops Toronto Pearson Intl New York LaGuardia

$4,667WestJet

Wed, Aug 12 - Mon, Aug 17

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Delta flights from Portland, Maine to Caribbean

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

Delta

Oct 20

PWM4:15 pmPortland

7h 29m

1 stop

SJU11:44 pmSan Juan Luis Munoz Marin Intl

Oct 26

SJU6:45 amSan Juan Luis Munoz Marin Intl

8h 50m

1 stop

PWM3:35 pmPortland

$352

Delta

Nov 2

PWM6:01 amPortland

6h 39m

1 stop

GCM12:40 pmGeorge Town Owen Roberts Intl

Nov 10

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 43m

1 stop

PWM11:33 pmPortland

$357

Delta

Nov 2

PWM6:01 amPortland

6h 39m

1 stop

GCM12:40 pmGeorge Town Owen Roberts Intl

Nov 12

GCM1:50 pmGeorge Town Owen Roberts Intl

22h 18m

2 stops

PWM12:08 pmPortland

$362

JetBlue flights from Portland, Maine to Caribbean

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

JetBlue

Sep 29

PWM6:00 amPortland

7h 39m

1 stop

SJU1:39 pmSan Juan Luis Munoz Marin Intl

Oct 3

SJU10:30 amSan Juan Luis Munoz Marin Intl

13h 24m

1 stop

PWM11:54 pmPortland

$433

JetBlue

Oct 15

PWM6:00 amPortland

7h 49m

1 stop

SJU1:49 pmSan Juan Luis Munoz Marin Intl

Oct 24

SJU3:00 pmSan Juan Luis Munoz Marin Intl

8h 52m

1 stop

PWM11:52 pmPortland

$459

JetBlue

Oct 15

PWM6:00 amPortland

15h 02m

2 stops

SJU9:02 pmSan Juan Luis Munoz Marin Intl

Oct 24

SJU3:00 pmSan Juan Luis Munoz Marin Intl

8h 52m

1 stop

PWM11:52 pmPortland

$464

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

Cheapest round-trip

PortlandSaint Thomas Island

PWM Portland - STT Saint Thomas Island Cyril E King

PWMSTT

Portland

Sat 10/24

4:54 pm-12:58 pm

2 stops20h 04m

Saint Thomas Island Cyril E King

Thu 10/29

1:48 pm-11:06 am

2 stops21h 18m

$200

PortlandSaint Thomas Island

PWM Portland - STT Saint Thomas Island Cyril E King

PWMSTT

Portland

Thu 10/29

4:40 pm-12:58 pm

2 stops20h 18m

Saint Thomas Island Cyril E King

Mon 11/2

3:15 pm-10:37 am

2 stops20h 22m

$200

Quickest round-trip

PortlandNassau

PWM Portland - NAS Nassau Intl

PWMNAS

Portland

Mon 10/19

6:00 am-1:33 pm

1 stop7h 33m

Nassau Intl

Thu 10/22

2:35 pm-11:28 pm

1 stop8h 53m

$321

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 9/16

4:20 pm-11:49 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Wed 9/23

1:16 pm-11:56 pm

1 stop10h 40m

$346

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 11/11

12:45 pm-11:20 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Wed 11/18

6:40 am-2:45 pm

1 stop9h 05m

$346

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Wed 11/11

10:25 am-10:20 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Wed 11/18

6:10 am-2:45 pm

2 stops9h 35m

$346

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Sat 9/19

6:00 am-8:38 pm

2 stops14h 38m

San Juan Luis Munoz Marin Intl

Sat 9/19

1:00 am-9:08 am

1 stop8h 08m

$347

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Tue 10/20

6:01 am-4:49 pm

1 stop10h 48m

San Juan Luis Munoz Marin Intl

Sat 10/24

1:15 pm-12:10 am

1 stop10h 55m

$352

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Mon 9/28

7:00 am-4:45 pm

2 stops33h 45m

San Juan Luis Munoz Marin Intl

Sat 10/3

9:30 am-5:51 pm

1 stop8h 21m

$391

PortlandSan Juan

PWM Portland - SJU San Juan Luis Munoz Marin Intl

PWMSJU

Portland

Mon 9/28

7:00 am-4:45 pm

2 stops33h 45m

San Juan Luis Munoz Marin Intl

Sat 10/3

9:30 am-5:51 pm

1 stop8h 21m

$392

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, September 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 $418. If you don’t want to visit Caribbean in September, then you should wait until January to fly from Portland, Maine, when ticket prices are also cheap, with an average price of $456.

How far in advance should I book a flight from Portland, Maine 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 $500 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 $287 on momondo.

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

You could potentially save up to 23% 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 53m
Direct flights	None

The fastest flight from Portland, Maine to Caribbean takes 5h 53m

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

Search flight deals

Frequently asked questions about flying from Portland, Maine 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 August 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
JetBlue	PriceFrom $174	Free Cancellation	Rating 7.1 3,034 reviews	Search JetBlue flights
Delta	PriceFrom $216	Free Cancellation	Rating 7.8 8,505 reviews	Search Delta flights
United Airlines	PriceFrom $246	Free Cancellation	Rating 7.4 10,104 reviews	Search United Airlines flights
American Airlines	PriceFrom $256	Free Cancellation	Rating 7.1 11,904 reviews	Search American Airlines flights
Southwest	PriceFrom $300	Free Cancellation	Rating 8.0 4,220 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.