
Round-trip from | $394 (Southwest) |
|---|---|
One-way from | $176 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $619 |
Fly from
Fly to
Route
Depart
Return
Price
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 1/12
9:45 pm-1:05 pm
1 stop11h 20m
San Juan Luis Munoz Marin Intl
Thu 1/15
2:15 pm-10:15 pm
1 stop12h 00m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 1/19
6:00 am-11:45 pm
2 stops13h 45m
San Juan Luis Munoz Marin Intl
Wed 1/28
7:00 am-5:35 pm
2 stops14h 35m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Fri 1/30
6:45 am-12:35 am
2 stops13h 50m
San Juan Luis Munoz Marin Intl
Sat 2/7
6:00 am-4:40 pm
2 stops14h 40m
PortlandPunta Cana
PDX - PUJ
PDXPUJ
Portland
Thu 12/11
7:04 am-1:47 pm
1 stop26h 43m
Punta Cana
Mon 12/15
6:08 pm-1:50 pm
2 stops23h 42m
PortlandOranjestad
PDX - AUA
PDXAUA
Portland
Wed 4/15
1:45 pm-12:14 pm
2 stops19h 29m
Oranjestad Reina Beatrix
Tue 4/21
1:55 pm-9:25 am
2 stops22h 30m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Tue 3/3
5:05 am-9:26 pm
2 stops12h 21m
San Juan Luis Munoz Marin Intl
Tue 3/3
2:05 am-2:48 pm
2 stops16h 43m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Sat 1/31
7:00 am-9:00 pm
1 stop10h 00m
San Juan Luis Munoz Marin Intl
Fri 2/6
2:05 am-2:46 pm
2 stops16h 41m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 1/19
3:50 pm-12:55 pm
2 stops17h 05m
San Juan Luis Munoz Marin Intl
Tue 1/27
2:05 am-2:48 pm
2 stops16h 43m
PortlandMontego Bay
PDX - MBJ
PDXMBJ
Portland
Wed 12/17
7:29 am-2:29 pm
1 stop28h 00m
Montego Bay Sangster Intl
Wed 12/24
10:24 am-8:50 pm
1 stop13h 26m
PortlandSan Juan
PDX - SJU
PDXSJU
Portland
Mon 1/12
6:30 am-11:10 pm
2 stops12h 40m
San Juan Luis Munoz Marin Intl
Sun 1/18
5:40 am-3:40 pm
2 stops14h 00m
Currently, August is the cheapest month in which you can book a flight from Portland to Caribbean (average of $186). Flying from Portland to Caribbean in December is currently the most expensive (average of $412). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
One of the essential ways to save on airfare from Portland to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 15% on airfare.
Travelers seeking maximum savings on their Portland to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
Crew
Food
Boarding
Entertainment
Comfort
Overall
Reviews
Mike,Aug 2025
OKC - AUS
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$185 | Average$540 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$190 | Average$688 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$248 | Average$415 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$343 | Average$707 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$400 | Average$692 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$431 | Average$587 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$444 | Average$726 | FlexibilityNo cancel fee | On-time63% |