To save on the cost of your flight from Portland to Caribbean, book at least 27 days before your planned departure. Booking around this time can save you about 85% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $458 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $671.
Our data shows that September tends to be the cheapest month to fly to Caribbean from Portland. Users have commonly found prices around $533 for the month, but tickets can be as low as $265. Due to multiple factors, prepare for potentially higher prices in December.
When flying from Portland to Caribbean, 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
$256 - $565
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Wed 5/29
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Mon 6/10
1 stop19h 53m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Tue 8/20
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Mon 8/26
1 stop18h 47m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Mon 5/27
1 stop14h 33m
San Juan Luis Munoz Marin Intl
Mon 6/3
1 stop19h 20m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sun 6/9
2 stops11h 32m
San Juan Luis Munoz Marin Intl
Mon 6/17
1 stop19h 53m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Fri 9/20
1 stop9h 18m
San Juan Luis Munoz Marin Intl
Tue 9/24
2 stops15h 00m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Wed 6/5
2 stops11h 12m
San Juan Luis Munoz Marin Intl
Thu 6/13
2 stops17h 38m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Fri 8/16
1 stop11h 27m
San Juan Luis Munoz Marin Intl
Tue 8/20
1 stop13h 41m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sat 10/19
2 stops14h 59m
San Juan Luis Munoz Marin Intl
Tue 10/22
1 stop11h 18m
PortlandNassau Intl
PDX - NAS
PDXNAS
Portland
Fri 6/7
2 stops32h 45m
Nassau Intl
Fri 6/14
2 stops24h 10m
No data available for this route at this time. Please check back soon.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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.
Overall
Food
Boarding
Comfort
Crew
Entertainment
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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