$114+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — PWM
Aug 25 — Sep 11
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 August 20, 2025.
Round-trip from | $683 (JetBlue) |
|---|---|
One-way from | $114 (American Airlines) |
Find flight deals from Caribbean to Portland
Cheapest flights from Caribbean to PortlandExplore 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 August 20, 2025.
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 August 20, 2025.
This United Airlines deal was found by Cheapflights users on 8/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/182:05 amSJU - PWM
2 stops12h 21mUnited Airlines
Tue 8/266:14 amPWM - SJU
2 stops14h 24mUnited Airlines
Deal found 8/18![United Airlines logo]()
$453
This Southwest deal was found by Cheapflights users on 8/18. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/191:35 pmSJU - PWM
2 stops8h 50mSouthwest
Tue 8/263:40 pmPWM - SJU
1 stop6h 50mSouthwest
Deal found 8/18![Southwest logo]()
$552
This JetBlue deal was found by Cheapflights users on 8/19. 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.
Wed 9/36:00 amSJU - PWM
1 stop7h 22mJetBlue
Sun 9/72:17 pmPWM - SJU
1 stop7h 07mJetBlue
Deal found 8/19![JetBlue logo]()
$683
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/21:05 amSJU - PWM
1 stop8h 19mUnited Airlines
Sun 9/73:11 pmPWM - SJU
1 stop8h 46mUnited Airlines
Deal found 8/19![United Airlines logo]()
$724
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 9/31:40 pmSJU - PWM
2 stops10h 05mAmerican Airlines
Sun 9/76:00 amPWM - SJU
2 stops12h 15mAmerican Airlines
Deal found 8/19![American Airlines logo]()
$865
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 August 20, 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
Wed 9/3
6:00 am-1:22 pm
1 stop7h 22m
Portland
Sun 9/7
2:17 pm-9:24 pm
1 stop7h 07m
$683
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Tue 9/2
1:05 am-9:24 am
1 stop8h 19m
Portland
Sun 9/7
3:11 pm-11:57 pm
1 stop8h 46m
$724
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Wed 9/3
1:40 pm-11:45 pm
2 stops10h 05m
Portland
Sun 9/7
6:00 am-6:15 pm
2 stops12h 15m
$865
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Sat 9/20
3:55 pm-12:29 pm
2 stops20h 34m
$114
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Sat 9/20
6:00 pm-12:34 am
1 stop6h 34m
$138
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Fri 9/12
1:32 pm-12:34 am
1 stop11h 02m
$138
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Sun 9/21
1:25 pm-10:07 pm
1 stop8h 42m
$141
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Fri 9/12
12:01 pm-12:29 pm
2 stops24h 28m
$144
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Thu 9/25
6:05 pm-10:07 pm
1 stop28h 02m
$172
San JuanPortland
SJU - PWM
SJUPWM
San Juan Luis Munoz Marin Intl
Sat 9/13
6:00 am-1:22 pm
1 stop7h 22m
$182
Showing 1-10 of 12 results
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 August 20, 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.
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 August 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Caribbean to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.3
Boarding
8.2
Crew
8.5
Comfort
7.9
Entertainment
7.9
Overall
8.0
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Food
7.3
Boarding
8.2
Crew
8.5
Comfort
7.9
Entertainment
7.9
Overall
8.0
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Food
7.3
Boarding
8.2
Crew
8.5
Comfort
7.9
Entertainment
7.9
Overall
8.0
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
Food
7.3
Boarding
8.2
Crew
8.5
Comfort
7.9
Entertainment
7.9
Overall
8.0
Reviews
1 / 20
6.0
GoodMorgan Rae,Aug 2025
BRU - JFK
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBrunswick
North Conway
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.
Top 2 airlines flying from Caribbean to Portland
Discover the top 2 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 August 20, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$370 | Average$538 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$383 | Average$516 | FlexibilityNo cancel fee | On-time69% |