HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$166+ Cheap flights from Caribbean 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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Jun 23 — Jun 301
Mon 6/23
Mon 6/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean to Portland

Keep the following information in mind while searching for Caribbean to Portland flight deals. Data was last updated June 18, 2025.

Round-trip from

$353
(American Airlines)

One-way from

$166
(Delta)

Popular in

April

Cheapest in

February

Average price

$378
From Caribbean to Portland
Search Deals
One-way flight from Caribbean to Portland
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2025
Search Deals

Find flight deals from Caribbean to Portland

Cheapest flights from Caribbean to Portland
Explore the most affordable flight options available from Caribbean to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 18, 2025.

This American Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:30 amSJU - PWM
1 stop9h 24mAmerican Airlines
Fri 11/284:18 pmPWM - SJU
1 stop6h 13mAmerican Airlines
Deal found 6/16$353
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/151:34 pmSJU - PWM
1 stop11h 14mDelta
Sat 8/236:00 amPWM - SJU
1 stop10h 36mDelta
Deal found 6/18$395
This Southwest deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/137:20 amSJU - PWM
1 stop11h 05mSouthwest
Sun 8/175:35 amPWM - SJU
1 stop6h 50mSouthwest
Deal found 6/16$469
This JetBlue deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/123:25 amSJU - PWM
1 stop9h 58mJetBlue
Sun 8/176:10 amPWM - SJU
1 stop8h 47mJetBlue
Deal found 6/16$515
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/121:05 amSJU - PWM
2 stops9h 02mUnited Airlines
Sun 8/178:00 amPWM - SJU
2 stops15h 54mUnited Airlines
Deal found 6/16$598
This Mytrip deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/101:37 amSJU - PWM
2 stops15h 59mMultiple Airlines
Thu 8/1412:46 pmPWM - SJU
2 stops25h 31mMultiple Airlines
Deal found 6/15$671

Cheapflights Fare Finder

Customize your flight search to find flights from Caribbean to Portland 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, Cheapflights users made 2,558,603 searches. Data last updated June 18, 2025.
Use the filters below to find and compare flights from Caribbean to Portland that are best for you.

Fly from

Caribbean

Fly to

Portland

Route

Depart

Return

Price

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Mon 11/24

6:30 am-2:54 pm

1 stop9h 24m

Portland

Fri 11/28

4:18 pm-11:31 pm

1 stop6h 13m

$353

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 8/15

1:34 pm-12:48 am

1 stop11h 14m

Portland

Sat 8/23

6:00 am-4:36 pm

1 stop10h 36m

$395

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Wed 8/13

7:20 am-6:25 pm

1 stop11h 05m

Portland

Sun 8/17

5:35 am-12:25 pm

1 stop6h 50m

$469

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 8/12

3:25 am-1:23 pm

1 stop9h 58m

Portland

Sun 8/17

6:10 am-2:57 pm

1 stop8h 47m

$515

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Tue 8/12

1:05 am-10:07 am

2 stops9h 02m

Portland

Sun 8/17

8:00 am-11:54 pm

2 stops15h 54m

$598

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sun 8/10

1:37 am-5:36 pm

2 stops15h 59m

Portland

Thu 8/14

12:46 pm-2:17 pm

2 stops25h 31m

$671

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 7/19

1:34 pm-12:57 am

1 stop11h 23m

$166

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Fri 7/18

3:34 am-6:13 pm

1 stop14h 39m

$207

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 7/19

3:05 am-12:17 am

1 stop21h 12m

$247

San JuanPortland

SJU - PWM

SJUPWM

San Juan Luis Munoz Marin Intl

Sat 7/19

1:37 am-12:21 pm

2 stops34h 44m

$297

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

Showing 1-10 of 12 results
1
2

Best time to book a flight from Caribbean to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Caribbean 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 to Portland

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

Currently, January is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $296). Flying from Caribbean 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 CB to PWM?

Find hourly flight availability from Caribbean 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 June 18, 2025.

When flying from Caribbean 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

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.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated June 18, 2025.
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
7,964 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
8,810 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
2,924 reviews
Southwest
8.0
Very good
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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
4,280 reviews

Boarding

8.2

Entertainment

7.6

Food

7.1

Overall

8.0

Comfort

8.0

Crew

8.6

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

Find useful and relevant information for your journey from Caribbean 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?

    Most people fly into Portland (PWM) if they book a flight to Portland from Caribbean. Portland is conveniently located just 2.9 mi from Portland’s city center.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $166. Users have also found prices from $207 and $247 on Frontier and JetBlue, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Caribbean 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 to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Caribbean to Portland, Maine (average of $296). Flying from Caribbean 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

Traveling to a place near Caribbean?

Book flights to Caribbean if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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 to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to Boston flights
Dallas/Fort Worth to Boston flights
Reagan-National to Boston flights
O'Hare Intl to Boston flights
Atlanta to Boston flights
Baltimore to Boston flights
Miami to Boston flights
Dulles Intl to Boston flights
Newark to Boston flights
Raleigh to Boston flights
San Francisco to Boston flights
Denver to Boston flights
Fort Lauderdale to Boston flights
LaGuardia to Boston flights
Seattle to Boston flights
Hobby to Boston flights
Charlotte to Boston flights
Orlando to Boston flights
John F Kennedy Intl to Boston flights
Philadelphia to Boston flights
George Bush Intcntl to Boston flights
Austin to Boston flights
Tampa to Boston flights
Minneapolis to Boston flights
San Diego to Boston flights
Kansas City to Boston flights
Love Field to Boston flights
Portland to Boston flights
Salt Lake City to Boston flights
Cincinnati to Boston flights
Dulles Intl to Portland flights
Cleveland to Boston flights
John F Kennedy Intl to Portland flights
Pittsburgh to Boston flights
LaGuardia to Portland flights
Sky Harbor Intl to Boston flights
Detroit to Boston flights
Columbus to Boston flights
Milwaukee to Boston flights
O'Hare Intl to Portland flights
Reagan-National to Portland flights
Heathrow to Boston flights
Newark to Portland flights
Ontario to Boston flights
West Palm Beach to Boston flights
Charles de Gaulle to Boston flights
Denver to Portland flights
Luis Munoz Marin Intl to Boston flights
Nashville to Boston flights
New Orleans to Boston flights

Top 3 airlines flying from Caribbean to Portland

Discover the top 3 airlines that operate flights from Caribbean to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$370Average$594FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$383Average$530FlexibilityNo cancel feeOn-time69%
JetBlueCheapest$455Average$660FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.