$188 Find Cheap Flights from Oregon to Caribbean

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Useful Info

Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$188
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Portland to San Juan

FAQs for booking flights from Oregon to Caribbean

  • How does KAYAK find such low prices on flights from Oregon to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oregon to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oregon to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oregon to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Oregon to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Oregon to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Caribbean?

    Based on KAYAK data, the cheapest day to fly to Caribbean is Tuesday where round-trip tickets can be as cheap as $454. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $655 on average.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $428 on average. Morning departures are around 41% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $602.

  • What is the cheapest month to fly from Oregon to Caribbean?

    The cheapest month for flights from Oregon to Caribbean is September, when tickets cost $566 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $881 and $778 respectively.

  • How far in advance should I book a flight from Oregon to Caribbean?

    To get a below average price on the flight from Oregon to Caribbean, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

  • How long is the flight to Caribbean?

    An average nonstop flight from Oregon to Caribbean takes 16h 07m, covering a distance of 3400 miles. The shortest route is Portland (PDX) to Freeport (FPO) with an average flight time of 9h 02m.

  • What are the most popular destinations in Caribbean?

    Based on KAYAK flight searches, the most popular destination is Punta Cana (17% of total searches to Caribbean). The next most popular destinations are Nassau (12%) and Montego Bay (9%). Searches for flights to Saint Thomas Island (8%), to Oranjestad (8%) and to Providenciales (5%) are also popular.

Book cheap flights from Oregon to Caribbean

Recent round-trip flight deals

10/17Fri
2 stopsSpirit Airlines
23h 11mPDX-SJU
10/20Mon
2 stopsSpirit Airlines
22h 49mSJU-PDX
$342
8/17Sun
2 stopsSpirit Airlines
16h 51mBOI-SJU
8/21Thu
2 stopsSpirit Airlines
26h 59mSJU-BOI
$355
8/8Fri
3 stops
29h 58mPDX-SJU
8/14Thu
2 stops
29h 45mSJU-PDX
$366
8/29Fri
3 stops
27h 24mPDX-SJU
9/11Thu
3 stops
26h 06mSJU-PDX
$367
8/15Fri
2 stopsFrontier
21h 38mPDX-SJU
8/21Thu
2 stopsFrontier
20h 15mSJU-PDX
$377
11/12Wed
2 stopsDelta
15h 10mBOI-SJU
11/15Sat
2 stopsDelta
16h 16mSJU-BOI
$385
9/16Tue
1 stopAmerican Airlines
14h 56mPDX-SJU
10/1Wed
2 stopsAmerican Airlines
13h 28mSJU-PDX
$399
11/16Sun
2 stopsDelta
13h 03mPDX-SJU
12/6Sat
1 stopDelta
13h 03mSJU-PDX
$409
9/10Wed
2 stopsFrontier
16h 19mPDX-SJU
9/18Thu
2 stopsFrontier
19h 12mSJU-PDX
$418
12/2Tue
1 stopAmerican Airlines
13h 57mPDX-SJU
12/11Thu
2 stopsAmerican Airlines
12h 41mSJU-PDX
$419

Search by stops

Search by airline

Search by price

Recent one-way flight deals

9/3Wed
2 stopsSpirit Airlines
15h 01mPDX-SJU
$188
9/3Wed
2 stopsSpirit Airlines
15h 01mPDX-SJU
$191
11/11Tue
2 stopsAmerican Airlines
13h 24mPDX-SJU
$200
9/13Sat
2 stopsAmerican Airlines
14h 30mPDX-SJU
$203
9/14Sun
1 stopDelta
11h 09mPDX-SJU
$205
8/15Fri
1 stopAlaska Airlines
19h 24mPDX-NAS
$216
9/14Sun
1 stopSouthwest
12h 35mPDX-SJU
$220
8/14Thu
2 stopsDelta
9h 54mPDX-NAS
$221
9/14Sun
2 stopsSouthwest
12h 30mPDX-SJU
$248
11/9Sun
3 stopsAlaska Airlines
17h 35mBOI-SJU
$460

Search by stops

Search by airline

Search by price

Last minute flights from Oregon to Caribbean

Last minute flight, train and bus deals

7/20Sun
multi-stopFrontier
18h 39mPDX-SJU
7/22Tue
multi-stopFrontier
18h 56mSJU-PDX
$472
7/21Mon
multi-stop
16h 28mPDX-MBJ
7/29Tue
multi-stop
20h 28mMBJ-PDX
$558
7/18Fri
multi-stopAmerican Airlines
11h 28mPDX-NAS
8/20Wed
multi-stopAmerican Airlines
14h 33mNAS-PDX
$586
7/21Mon
multi-stopSpirit Airlines
24h 02mBOI-SJU
7/31Thu
multi-stopSpirit Airlines
19h 15mSJU-BOI
$627
7/20Sun
multi-stopAmerican Airlines
12h 45mPDX-SJU
7/28Mon
multi-stopAmerican Airlines
12h 43mSJU-PDX
$635
7/20Sun
multi-stopSpirit Airlines
17h 52mPDX-SJU
7/29Tue
multi-stopSpirit Airlines
23h 11mSJU-PDX
$647
7/21Mon
multi-stopJetBlue
11h 50mPDX-MBJ
7/28Mon
multi-stopJetBlue
29h 30mMBJ-PDX
$669
7/21Mon
multi-stopSouthwest
11h 30mPDX-SJU
7/25Fri
multi-stopSouthwest
12h 25mSJU-PDX
$690
7/21Mon
multi-stopJetBlue
11h 50mPDX-MBJ
7/28Mon
multi-stopJetBlue
33h 40mMBJ-PDX
$735
7/20Sun
multi-stopSouthwest
12h 30mPDX-MBJ
7/29Tue
multi-stopSouthwest
11h 35mMBJ-PDX
$875

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Caribbean

Cabin class types available on flights to Oregon

Cabin classes available on flights to Oregon. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.