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 Islands 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.
Flights from Portland, Maine to Caribbean Islands lean towards being more expensive in November. Prices are generally better when you fly from Portland, Maine to Caribbean Islands in September, with the cheapest ticket starting at $272.
When flying from Portland, Maine to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Fly from
Fly to
Budget
$270 - $489
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
mié. 9/11
1 stop6h 39m
San Juan Luis Munoz Marin Intl
jue. 9/26
1 stop6h 12m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sáb. 11/9
2 stops21h 10m
San Juan Luis Munoz Marin Intl
mié. 11/13
2 stops17h 17m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sáb. 11/9
1 stop6h 47m
San Juan Luis Munoz Marin Intl
mié. 11/13
1 stop6h 58m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
dom. 8/25
1 stop7h 42m
San Juan Luis Munoz Marin Intl
mié. 8/28
1 stop7h 19m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
lun. 11/18
2 stops19h 16m
San Juan Luis Munoz Marin Intl
vie. 12/13
2 stops24h 13m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
dom. 6/9
1 stop8h 50m
San Juan Luis Munoz Marin Intl
jue. 6/13
1 stop9h 14m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
mié. 9/11
2 stops17h 41m
San Juan Luis Munoz Marin Intl
jue. 9/26
2 stops8h 54m
PortlandSan Juan Luis Munoz Marin Intl
PWM - SJU
PWMSJU
Portland
sáb. 6/8
1 stop10h 08m
San Juan Luis Munoz Marin Intl
vie. 6/14
1 stop6h 42m
PortlandSaint Thomas Island Cyril E King
PWM - STT
PWMSTT
Portland
mié. 6/12
2 stops21h 32m
Saint Thomas Island Cyril E King
jue. 7/11
1 stop17h 27m
No data available for this route at this time. Please check back soon.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
Entertainment
Comfort
Overall
Boarding
Crew
Food
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.
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Millions of users choose and trust Cheapflights to book the best flight deals from Portland to Caribbean Islands for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.
Certainly. Search results for flights to Caribbean Islands from Portland shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.
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