When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 19 days in advance, which can save you up to 110% on flights from Portland, Maine to Caribbean compared to booking the week you need them. Waiting 19 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $248. For sooner than that we have options available in the next 3 days from $539.
Our data shows that September tends to be the cheapest month to fly to Caribbean from Portland, Maine. Users have commonly found prices around $504 for the month, but tickets can be as low as $272. Due to multiple factors, prepare for potentially higher prices in November.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Portland, Maine to Caribbean as you normally would.
Fly from
Fly to
Budget
$238 - $468
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Tue 6/25
1 stop6h 18m
San Juan Luis Munoz Marin Intl
Thu 7/4
1 stop7h 40m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Wed 10/2
1 stop6h 39m
San Juan Luis Munoz Marin Intl
Sun 10/6
1 stop6h 12m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Wed 10/2
1 stop7h 25m
San Juan Luis Munoz Marin Intl
Sat 10/5
1 stop9h 22m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Sun 6/9
1 stop8h 50m
San Juan Luis Munoz Marin Intl
Thu 6/13
1 stop9h 14m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Wed 10/9
1 stop6h 39m
San Juan Luis Munoz Marin Intl
Sat 10/19
1 stop6h 12m
PortlandOranjestad Reina Beatrix
PWM - AUA
PWMAUA
Portland
Sat 9/14
2 stops21h 32m
Oranjestad Reina Beatrix
Sat 9/21
2 stops21h 01m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Wed 10/2
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Sat 10/5
2 stops13h 27m
PortlandNassau Intl
PWM - NAS
PWMNAS
Portland
Fri 10/25
1 stop6h 02m
Nassau Intl
Fri 11/1
1 stop10h 08m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Fri 6/28
1 stop13h 16m
San Juan Luis Munoz Marin Intl
Fri 7/5
2 stops28h 48m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Boarding
Comfort
Entertainment
Crew
Food
Overall
Reviews
Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.
Cheapflights helps you search for flights from Portland to Caribbean via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.
Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Portland to Caribbean for you. Better yet — we are completely free to use.
Need flexible booking options for your flight to Caribbean from Portland? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
Of course! You can now track prices for flights from Portland to Caribbean and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.