$151 Find Cheap Flights from Caribbean to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 8/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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

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

Save 24% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Portland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Caribbean to Portland

Mon, Sep 14 - Tue, Sep 22
Delta Logo
7:00 am - 1:54 pm
SJU
-
PWM
6h 54m
1 stop
Delta Logo
6:00 am - 4:31 pm
PWM
-
SJU
10h 31m
1 stop
$322Delta
Wed, May 20 - Mon, May 25
United Airlines Logo
1:00 am - 9:11 am
SJU
-
PWM
8h 11m
1 stop
United Airlines Logo
5:15 am - 12:34 pm
PWM
-
SJU
7h 19m
1 stop
$368United Airlines
Thu, Aug 6 - Thu, Aug 13
Delta Logo
5:50 pm - 12:59 am
SJU
-
PWM
7h 09m
1 stop
Delta Logo
6:00 am - 4:33 pm
PWM
-
SJU
10h 33m
1 stop
$379Delta
Mon, Sep 14 - Tue, Sep 22
Southwest Logo
5:30 am - 12:25 pm
SJU
-
PWM
6h 55m
1 stop
Southwest Logo
5:45 am - 4:25 pm
PWM
-
SJU
10h 40m
2 stops
$402Southwest
Sat, Aug 22 - Wed, Aug 26
American Airlines Logo
7:05 am - 10:44 pm
SJU
-
PWM
15h 39m
1 stop
American Airlines Logo
6:00 am - 4:03 pm
PWM
-
SJU
10h 03m
2 stops
$417American Airlines
Fri, May 29 - Sun, May 31
JetBlue Logo
6:30 am - 1:35 pm
SJU
-
PWM
7h 05m
1 stop
JetBlue Logo
6:00 am - 3:34 pm
PWM
-
SJU
9h 34m
1 stop
$441JetBlue
Tue, Jun 2 - Tue, Jun 9
JetBlue Logo
6:30 am - 1:35 pm
SJU
-
PWM
7h 05m
1 stop
JetBlue Logo
2:37 pm - 1:38 am
PWM
-
SJU
11h 01m
1 stop
$448JetBlue
Fri, Jul 10 - Sun, Jul 12
JetBlue Logo
3:10 pm - 12:14 am
SJU
-
PWM
9h 04m
1 stop
JetBlue Logo
1:16 pm - 10:39 pm
PWM
-
SJU
9h 23m
1 stop
$450JetBlue
Tue, Aug 25 - Sat, Aug 29
JetBlue Logo
5:01 am - 12:21 pm
SJU
-
PWM
7h 20m
1 stop
JetBlue Logo
6:40 am - 1:58 pm
PWM
-
SJU
7h 18m
1 stop
$451JetBlue
Fri, Jun 12 - Sun, Jul 5
JetBlue Logo
5:45 pm - 12:52 am
SJU
-
PWM
7h 07m
1 stop
JetBlue Logo
2:05 pm - 10:27 pm
PWM
-
SJU
8h 22m
1 stop
$452JetBlue
Useful Info

Good to know

Cheapest flight$151
Flight from San Juan to Portland

FAQs for booking flights from Caribbean to Portland

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

    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 Caribbean to Portland.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from 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 Caribbean to Portland?

    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 to Portland with an airline and back to Caribbean with another airline.

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

    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 to Portland from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean to Portland

 
Need help choosing which airline to fly with from Caribbean to Portland? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11668 reviews
6.4Food
6.9Entertainment
7.2Comfort
7.5Boarding
7.9Crew
Airline reviews

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

8.0 ExcellentConnie, May 2026
PHX - MKE
Read more American Airlines reviews

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Jackson
Freeport
Bartlett
Oxford
Windham
Intervale
Tamworth
Falmouth
Durham
Waterford

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Portland (PWM)