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 79% 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 $266. 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
$287 - $600
Route
Depart
Return
Price
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Wed 7/10
1 stop15h 14m
San Juan Luis Munoz Marin Intl
Wed 7/17
2 stops13h 12m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Mon 9/2
2 stops12h 16m
San Juan Luis Munoz Marin Intl
Sat 9/14
2 stops20h 37m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Wed 7/10
2 stops17h 26m
San Juan Luis Munoz Marin Intl
Wed 7/17
2 stops13h 12m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sat 7/20
2 stops11h 13m
San Juan Luis Munoz Marin Intl
Fri 7/26
2 stops18h 31m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sun 7/21
2 stops18h 13m
San Juan Luis Munoz Marin Intl
Fri 7/26
2 stops18h 31m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sat 11/9
1 stop13h 03m
San Juan Luis Munoz Marin Intl
Tue 11/12
1 stop14h 46m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Sun 9/29
1 stop12h 10m
San Juan Luis Munoz Marin Intl
Thu 10/3
1 stop11h 18m
PortlandSan Juan Luis Munoz Marin Intl
PDX - SJU
PDXSJU
Portland
Fri 11/8
1 stop18h 39m
San Juan Luis Munoz Marin Intl
Sat 11/16
1 stop28h 30m
PortlandNassau Intl
PDX - NAS
PDXNAS
Portland
Sun 7/7
1 stop8h 50m
Nassau Intl
Sun 7/14
1 stop12h 51m
No data available for this route at this time. Please check back soon.
Boarding
Comfort
Crew
Entertainment
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
Crew
Entertainment
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
Crew
Entertainment
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
Crew
Entertainment
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
Crew
Entertainment
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
Crew
Entertainment
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$143 | Average$313 | FlexibilityNo cancel fee | On-time62% |
Delta | Cheapest$205 | Average$573 | FlexibilityNo cancel fee | On-timeN/A |
JetBlue | Cheapest$212 | Average$599 | FlexibilityNo cancel fee | On-time62% |
Alaska Airlines | Cheapest$215 | Average$666 | FlexibilityNo cancel fee | On-time75% |
Spirit Airlines | Cheapest$239 | Average$370 | FlexibilityNo cancel fee | On-time65% |
United Airlines | Cheapest$292 | Average$633 | FlexibilityNo cancel fee | On-time69% |
American Airlines | Cheapest$305 | Average$680 | FlexibilityNo cancel fee | On-time71% |
Sun Country Air | Cheapest$320 | Average$677 | FlexibilityNo cancel fee | On-time83% |
Linear Air Taxi | Cheapest$136,063 | Average$181,414 | FlexibilityNo cancel fee | On-timeN/A |