What are the cheapest airlines to fly from Caribbean Islands to Portland, Maine one-way?

To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $222. Southwest flights start at $272 while deals on American Airlines start at $358 one-way.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest month to fly from Caribbean Islands to Portland, Maine?

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, February can be a great choice for travel to Portland, Maine. Flights to Portland, Maine from Caribbean Islands in February are about $414 on average during February, but can be found for as low as $198.

What airport do you fly into for flights to Portland from Caribbean Islands?

Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Portland from Caribbean Islands.

Can I find deals for flights from Caribbean Islands to Portland that include hotel bookings?

Yes. In addition to deals on Caribbean Islands to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Caribbean Islands to Portland?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Portland.

Can I find deals for business class flights from Caribbean Islands to Portland?

Yes. Cheapflights offers flight deals from Caribbean Islands to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$222+ Flights from Caribbean Islands to Portland, ME

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Cheap flight deals from Caribbean Islands to Portland

Round-trip from	$275 (American Airlines)
One-way from	$222 (JetBlue)

From Caribbean Islands to Portland

Search Deals

One-way flight from Caribbean Islands to Portland

Search Deals

Find flight deals from Caribbean Islands to Portland

Cheapest flights from Caribbean Islands to Portland
Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2025.

Fri 8/295:15 pmSJU - PWM

2 stops17h 26mAmerican Airlines

Fri 9/126:00 amPWM - SJU

2 stops10h 20mAmerican Airlines

Deal found 7/23

$275

Wed 9/36:00 amSJU - PWM

1 stop7h 22mJetBlue

Sat 9/132:17 pmPWM - SJU

1 stop6h 42mJetBlue

Deal found 7/23

$413

Sat 8/307:00 amSJU - PWM

1 stop6h 56mDelta

Sat 9/132:41 pmPWM - SJU

1 stop9h 06mDelta

Deal found 7/23

$455

Sat 8/301:05 amSJU - PWM

1 stop8h 19mUnited Airlines

Wed 9/177:30 amPWM - SJU

1 stop6h 15mUnited Airlines

Deal found 7/23

$575

Sun 8/315:10 amSJU - PWM

2 stops11h 55mSouthwest

Sun 9/145:35 amPWM - SJU

2 stops10h 45mSouthwest

Deal found 7/23

$609

Best flights from Caribbean Islands to Portland
Discover carefully curated flight deals from Caribbean Islands to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 25, 2025.

Fri 8/295:15 pmSJU - PWM

2 stops17h 26mAmerican Airlines

Fri 9/126:00 amPWM - SJU

2 stops10h 20mAmerican Airlines

Deal found 7/23

$275

Wed 9/36:00 amSJU - PWM

1 stop7h 22mJetBlue

Sat 9/132:17 pmPWM - SJU

1 stop6h 42mJetBlue

Deal found 7/23

$413

Sat 8/307:00 amSJU - PWM

1 stop6h 56mDelta

Sat 9/132:41 pmPWM - SJU

1 stop9h 06mDelta

Deal found 7/23

$455

Sat 8/301:05 amSJU - PWM

1 stop8h 19mUnited Airlines

Wed 9/177:30 amPWM - SJU

1 stop6h 15mUnited Airlines

Deal found 7/23

$575

Sun 8/315:10 amSJU - PWM

2 stops11h 55mSouthwest

Sun 9/145:35 amPWM - SJU

2 stops10h 45mSouthwest

Deal found 7/23

$609

Last-minute flights from Caribbean Islands to Portland
Discover last-minute flight deals from Caribbean Islands to Portland. Data last updated July 25, 2025 and is based on user searches.

Fri 8/295:15 pmSJU - PWM

2 stops17h 26mAmerican Airlines

Fri 9/126:00 amPWM - SJU

2 stops10h 20mAmerican Airlines

Deal found 7/23

$275

Fri 8/291:50 pmSJU - PWM

1 stop10h 27mJetBlue

Mon 9/157:30 amPWM - SJU

1 stop7h 26mJetBlue

Deal found 7/23

$414

Sat 8/307:00 amSJU - PWM

1 stop6h 56mDelta

Sat 9/132:41 pmPWM - SJU

1 stop9h 06mDelta

Deal found 7/23

$455

Sat 8/301:05 amSJU - PWM

1 stop8h 19mUnited Airlines

Wed 9/177:30 amPWM - SJU

1 stop6h 15mUnited Airlines

Deal found 7/23

$575

Sun 8/315:10 amSJU - PWM

2 stops11h 55mSouthwest

Sun 9/145:35 amPWM - SJU

2 stops10h 45mSouthwest

Deal found 7/23

$609

One-way flights from Caribbean Islands to Portland
Search for one-way flight options from Caribbean Islands to Portland. Find affordable one-way fares based on user searches. Data last updated July 25, 2025.

Wed 8/61:50 pmSJU - PWM

1 stop10h 27mJetBlue

Deal found 7/24

$222

Wed 8/61:35 pmSJU - PWM

2 stops8h 50mSouthwest

Deal found 7/24

$272

Sat 8/232:11 amSJU - PWM

3 stops33h 23mMultiple Airlines

Deal found 7/22

$330

Sun 8/248:30 amSJU - PWM

1 stop12h 06mAmerican Airlines

Deal found 7/22

$358

Sun 8/247:00 amSJU - PWM

2 stops16h 03mUnited Airlines

Deal found 7/22

$523

Cheapflights Fare Finder

Use the filters below to find and compare flights from Caribbean Islands to Portland 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 8/29

5:15 pm-10:41 am

2 stops17h 26m

Portland

Fri 9/12

6:00 am-4:20 pm

2 stops10h 20m

$275

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 9/3

6:00 am-1:22 pm

1 stop7h 22m

Portland

Mon 9/15

7:30 am-4:43 pm

1 stop9h 13m

$413

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 8/30

7:00 am-1:56 pm

1 stop6h 56m

Portland

Sat 9/13

2:41 pm-11:47 pm

1 stop9h 06m

$455

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 8/30

1:05 am-9:24 am

1 stop8h 19m

Portland

Wed 9/17

7:30 am-1:45 pm

1 stop6h 15m

$575

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 8/31

5:10 am-5:05 pm

2 stops11h 55m

Portland

Sun 9/14

5:35 am-4:20 pm

2 stops10h 45m

$609

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 8/6

1:50 pm-12:17 am

1 stop10h 27m

$222

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 8/6

1:35 pm-10:25 pm

2 stops8h 50m

$272

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 8/6

4:43 pm-8:12 pm

3 stops27h 29m

$394

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 8/5

12:59 am-12:30 pm

2 stops11h 31m

$432

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Best time to book a flight from Caribbean Islands to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean Islands with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Portland

What is the cheapest month to book a flight from Caribbean Islands to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $296). Flying from Caribbean Islands to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from EPX to PWM?

When flying from Caribbean Islands to Portland, Maine, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Portland

Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Caribbean Islands to Portland by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,233 reviews

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,967 reviews

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

United Airlines

7.4

Good

8,880 reviews

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

JetBlue

7.3

Good

2,912 reviews

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

American Airlines

7.2

Good

10,000 reviews

Southwest

8.0

Very good

4,233 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly into for flights to Portland from Caribbean Islands?
Located just 2.9 mi from the city center, Portland (PWM) is the airport most travelers will use when flying to Portland from Caribbean Islands.
What are the cheapest airlines to fly from Caribbean Islands to Portland, Maine one-way?
To fly one-way, consider booking your trip with JetBlue, which is currently one of the cheapest options available, starting at $222. Southwest flights start at $272 while deals on American Airlines start at $358 one-way.
Can I find deals for flights from Caribbean Islands to Portland that include hotel bookings?
Yes. In addition to deals on Caribbean Islands to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Caribbean Islands to Portland?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean Islands to Portland.
Can I find deals for business class flights from Caribbean Islands to Portland?
Yes. Cheapflights offers flight deals from Caribbean Islands to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Caribbean Islands to Portland, Maine?
Currently, January is the cheapest month in which you can book a flight from Caribbean Islands to Portland, Maine (average of $296). Flying from Caribbean Islands to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Brunswick

North Conway

Auburn

Conway

Lewiston

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Caribbean Islands to Portland

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$370	Average$594	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$383	Average$530	FlexibilityNo cancel fee	On-time69%

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$222+ Cheap flights from Caribbean Islands to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/6. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Caribbean Islands to Portland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Caribbean Islands to Portland

Keep the following information in mind while searching for Caribbean Islands to Portland flight deals. Data was last updated July 25, 2025.

Round-trip from

One-way from

Find flight deals from Caribbean Islands to Portland

Cheapest flights from Caribbean Islands to PortlandExplore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2025.

Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Caribbean Islands to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean Islands with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Caribbean Islands to Portland

What is the cheapest month to book a flight from Caribbean Islands to Portland, Maine?

What is the cheapest time of day to fly from EPX to PWM?

Find hourly flight availability from Caribbean Islands to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 25, 2025.

Reviews of airlines servicing Portland

Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Caribbean Islands to Portland by reading reviews from past customers. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Caribbean Islands to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to Portland from Caribbean Islands?

What are the cheapest airlines to fly from Caribbean Islands to Portland, Maine one-way?

Can I find deals for flights from Caribbean Islands to Portland that include hotel bookings?

How can I find direct flights from Caribbean Islands to Portland?

Can I find deals for business class flights from Caribbean Islands to Portland?

What is the cheapest month to book a flight from Caribbean Islands to Portland, Maine?

Traveling to a place near Portland?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Portland

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Caribbean Islands to Portland

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Travel Smart

Cheapest flights from Caribbean Islands to Portland
Explore the most affordable flight options available from Caribbean Islands to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 25, 2025.