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
$264 - $539
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
ter 5/14
1 stop10h 45m
San Juan Luis Munoz Marin Intl
qui 5/30
1 stop6h 20m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sáb 6/8
1 stop10h 08m
San Juan Luis Munoz Marin Intl
sex 6/14
1 stop6h 42m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
ter 6/25
1 stop6h 03m
San Juan Luis Munoz Marin Intl
ter 7/2
1 stop6h 29m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sex 6/7
1 stop10h 08m
San Juan Luis Munoz Marin Intl
sex 6/14
1 stop11h 39m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sáb 6/8
2 stops17h 09m
San Juan Luis Munoz Marin Intl
sex 6/14
2 stops29h 05m
PortlandMontego Bay Sangster Intl
PWM - MBJ
PWMMBJ
Portland
sex 10/18
2 stops18h 27m
Montego Bay Sangster Intl
sex 10/25
2 stops19h 20m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
ter 6/25
1 stop6h 03m
San Juan Luis Munoz Marin Intl
sex 7/5
1 stop6h 29m
PortlandSanto Domingo Las Americas
PWM - SDQ
PWMSDQ
Portland
sáb 9/21
2 stops19h 50m
Santo Domingo Las Americas
dom 10/6
2 stops21h 21m
PortlandOranjestad Reina Beatrix
PWM - AUA
PWMAUA
Portland
sáb 6/8
3 stops28h 07m
Oranjestad Reina Beatrix
qui 6/13
2 stops18h 34m
No data available for this route at this time. Please check back soon.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
Entertainment
Boarding
Overall
Food
Comfort
Crew
Reviews
Terrible flight crew that skipped our row for service multiple times.
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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