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.
Search and Compare cheap Flights

Book your flight now with Cheapoair.com and save!
Cheap San Juan airfares from $2351/RT are provided by Cheapoair.com. Outbound flight is leaving on 06/04/2025, 10:00 am from Portland Intl (PDX) airport and arrives at San Juan (UAQ) at 09:15 pm. The flight time is 11 hours and 15 minutes. The Returning flight departes on 06/11/2025, 12:15 pm (other return dates are also available). Date posted: 19 Jan 2025
Price evolution for flights From Portland To Caribbean

Recent Deals on Flights from Portland to Caribbean:Roundtrip / Oneway
- $2351
Multiple Airlines
cheapoair.com check priceFrom To Departure Time Portland, OR (PDX) San Juan, AR (UAQ) 06/04/2025 10:00 am San Juan, AR (UAQ) Portland, OR (PDX) 06/11/2025 12:15 pm - We are sorry but currently there are no oneway offers for flights from Portland to Caribbean.
Please visit this page again later or try out our merchant comparison search. Good luck!
Recently found cheap flight deals
Ottawa To Punta Cana Multiple Airlines airfares from Ottawa in April
$519 Depart: 04/09/2025
Return: 04/15/2025
provided by Cheapoair.com
Trenton To Durham Multiple Airlines airfares from Trenton in May
$346 Depart: 05/06/2025
Return: 05/14/2025
provided by Cheapoair.com
Grand Rapids To Shanghai British Airways airfares from Grand Rapids in February
$1432 Depart: 02/26/2025
Return: 03/11/2025
provided by Cheapoair.com
Greenville/Spartanburg To Honolulu Alaska Airlines airfares from Greenville/Spartanburg in December
$2088 Depart: 12/25/2023
Return: 01/03/2024
provided by Cheapoair.com
Boston To Algiers Lufthansa airfares from Boston in March
$726 Depart: 03/24/2025
Return: 03/30/2025
provided by Cheapoair.com
Detroit To Newark Multiple Airlines airfares from Detroit in March
$685 Depart: 03/11/2025
Return: 03/26/2025
provided by Cheapoair.com
Orlando To Cancun Multiple Airlines airfares from Orlando in April
$258 Depart: 04/15/2025
Return: 04/22/2025
provided by Cheapoair.com
Houston To Portland Multiple Airlines airfares from Houston in April
$275 Depart: 04/30/2025
Return: 05/06/2025
provided by Cheapoair.com
Orange County To Santo Domingo Spirit Airlines airfares from Orange County in March
$563 Depart: 03/28/2025
Return: 04/02/2025
provided by Cheapoair.com
Specify your search details. Browse the cheapest flights from Portland to Caribbean, Caribbean hotel rooms and Portland to Caribbean vacation packages from the most popular providers, airline consolidators and travel search engines.
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 [...]