Cheap flights from Portland to Caribbean
Travel > Caribbean
Travel tip: Visit Montego Bay on your Holiday.Check our current prices for flights from Portland to Caribbean. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Portland to Caribbean, you will need to run a search below.
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Cheap San Juan airfares from $463/RT are provided by Cheapoair.com. Outbound flight is leaving on 03/02/2025, 10:16 am from Portland Intl (PDX) airport and arrives at San Juan Marin Intl (SJU) at 05:01 pm. The flight time is 6 hours and 45 minutes. The Returning flight departes on 03/11/2025, 12:49 pm (other return dates are also available). Date posted: 04 Jan 2025
Price evolution for flights From Portland To Caribbean

Recent Deals on Flights from Portland to Caribbean:Roundtrip / Oneway
- $463
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) San Juan, PR (SJU) 03/02/2025 10:16 am San Juan, PR (SJU) Portland, OR (PDX) 03/11/2025 12:49 pm - $504
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Montego Bay, JM (MBJ) 02/22/2025 08:28 pm Montego Bay, JM (MBJ) Portland, OR (PDX) 03/06/2025 01:07 pm - $626
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Punta Cana, DO (PUJ) 02/10/2025 05:30 pm Punta Cana, DO (PUJ) Portland, OR (PDX) 02/19/2025 01:39 pm - $667
Frontier Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Punta Cana, DO (PUJ) 02/14/2025 09:18 pm Punta Cana, DO (PUJ) Portland, OR (PDX) 02/19/2025 06:10 pm - $738
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Punta Cana, DO (PUJ) 02/14/2025 10:16 am Punta Cana, DO (PUJ) Portland, OR (PDX) 02/20/2025 04:48 pm - $136
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) San Juan, PR (SJU) 02/25/2025 08:28 pm - $167
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) San Juan, PR (SJU) 03/08/2025 07:32 pm - $249
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Punta Cana, DO (PUJ) 02/18/2025 10:16 am - $361
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Montego Bay, JM (MBJ) 04/29/2025 02:00 pm - $363
Spirit Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) Montego Bay, JM (MBJ) 03/09/2025 07:32 pm
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Know what to do when flying to Caribbean?
Montego Bay Travel Guide The grand dame of island resorts, Montego Bay, though welcoming a great wave of visitors, has saved its own identity. Mo Bay, as it is called, is the most cosmopolitan of Jamaican resorts, its main enticement being the array of luxurious hotels [...]Montego Bay History Montego Bay is the second city of Jamaica, and the capital of the parish of St. James. This city has a long history, which started with the settlement of the Spanish to Montego Bay after 1510. The reason the Spanish had named the city ‘Bahia [...]
Montego Bay Sightseeing The place to head for complete relaxation for your next vacation is none other than Montego Bay, Jamaica. Montego Bay is a hot tourist spot, and has been such since 1924. And as proof of this increased tourism in Montego Bay, you find a [...]
Montego Bay Nightlife Montego Bay is the place to visit in Jamaica not only for its many places of attraction, but also for its bustling and exciting nightlife. A visit to Montego Bay at night will be an unforgettable one; all you have to do is to go to the Hip [...]