When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 48 days in advance, which can save you up to 81% on flights from Portland, Maine to Caribbean compared to booking the week you need them. Waiting 48 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 $515. For sooner than that we have options available in the next 3 days from $690.
Our data shows that October tends to be the cheapest month to fly to Caribbean from Portland, Maine. Users have commonly found prices around $524 for the month, but tickets can be as low as $292. 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
$284 - $488
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Fri 6/7
1 stop10h 08m
San Juan Luis Munoz Marin Intl
Fri 6/14
1 stop11h 44m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Thu 6/27
1 stop9h 29m
San Juan Luis Munoz Marin Intl
Wed 7/3
1 stop10h 56m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Sun 6/9
1 stop12h 08m
San Juan Luis Munoz Marin Intl
Sat 6/15
1 stop10h 51m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Tue 6/25
1 stop7h 03m
San Juan Luis Munoz Marin Intl
Thu 7/4
1 stop6h 29m
PortlandOranjestad Reina Beatrix
PWM - AUA
PWMAUA
Portland
Tue 8/20
1 stop7h 01m
Oranjestad Reina Beatrix
Tue 8/27
2 stops18h 39m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Fri 6/7
1 stop10h 08m
San Juan Luis Munoz Marin Intl
Sat 6/15
1 stop6h 42m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Mon 6/24
1 stop6h 03m
San Juan Luis Munoz Marin Intl
Thu 7/4
1 stop7h 40m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Sun 6/2
2 stops22h 23m
San Juan Luis Munoz Marin Intl
Sun 6/9
2 stops28h 29m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
Tue 6/11
1 stop7h 35m
San Juan Luis Munoz Marin Intl
Mon 6/17
1 stop7h 19m
No data available for this route at this time. Please check back soon.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
Crew
Entertainment
Overall
Food
Boarding
Comfort
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.
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