$357 Find Cheap Flights from Portland to Jamaica

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Jamaica departing on 8/22. 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

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Cheap Flights from Portland to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Montego Bay
Montego Bay2 stops$357
Kingston
Kingston1 stop$468
Montego Bay
Montego Bay2 stops$357
Kingston
Kingston1 stop$468

Book Cheap Portland to Jamaica Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Jamaica 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 Portland to Jamaica

Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:50 pm - 12:03 pm
PWM
-
MBJ
18h 13m
2 stops
American Airlines Logo
3:20 pm - 11:12 am
MBJ
-
PWM
18h 52m
2 stops
$357American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:50 pm - 1:58 pm
PWM
-
MBJ
20h 08m
1 stop
American Airlines Logo
3:20 pm - 11:12 am
MBJ
-
PWM
18h 52m
2 stops
$363American Airlines
Tue, Jun 30 - Fri, Jul 3
American Airlines Logo
6:00 am - 1:30 pm
PWM
-
MBJ
8h 30m
1 stop
American Airlines Logo
5:17 pm - 10:36 am
MBJ
-
PWM
16h 19m
2 stops
$391American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:50 pm - 1:58 pm
PWM
-
MBJ
20h 08m
1 stop
American Airlines Logo
3:02 pm - 11:51 pm
MBJ
-
PWM
7h 49m
1 stop
$393American Airlines
Mon, Jun 29 - Mon, Jul 6
American Airlines Logo
6:54 pm - 1:55 pm
PWM
-
MBJ
20h 01m
1 stop
American Airlines Logo
5:17 pm - 2:16 pm
MBJ
-
PWM
19h 59m
2 stops
$397American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
6:50 pm - 1:58 pm
PWM
-
MBJ
20h 08m
1 stop
American Airlines Logo
1:35 pm - 11:01 pm
MBJ
-
PWM
8h 26m
1 stop
$401American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
5:57 pm - 9:25 am
PWM
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MBJ
16h 28m
1 stop
American Airlines Logo
3:20 pm - 11:12 am
MBJ
-
PWM
18h 52m
2 stops
$431American Airlines
Sat, May 23 - Mon, Jun 1
American Airlines Logo
7:19 pm - 1:30 pm
PWM
-
MBJ
19h 11m
1 stop
American Airlines Logo
5:17 pm - 1:38 pm
MBJ
-
PWM
19h 21m
2 stops
$441American Airlines
Thu, May 21 - Thu, May 28
JetBlue Logo
2:36 pm - 10:48 pm
PWM
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KIN
9h 12m
1 stop
JetBlue Logo
11:59 pm - 1:35 pm
KIN
-
PWM
12h 36m
1 stop
$468JetBlue
Tue, May 26 - Tue, Jun 2
JetBlue Logo
2:36 pm - 10:48 pm
PWM
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KIN
9h 12m
1 stop
JetBlue Logo
12:20 pm - 11:58 pm
KIN
-
PWM
10h 38m
1 stop
$472JetBlue
Booking Insights

KAYAK's insights & trends for Portland to Jamaica flights

Get data-powered insights and trends into flights from Portland to Jamaica to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Portland to Jamaica?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Portland to Jamaica were found on American Airlines ($357) and JetBlue ($468).

Good to know

Low seasonApril
Cheapest flight$357
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Portland to Montego Bay

FAQs - booking Jamaica flights

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

    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 Portland to Jamaica.

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

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

    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 Portland to Jamaica 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 Portland to Jamaica?

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

Reviews of the top 3 airlines serving from Portland to Jamaica

 
Need help choosing which airline to fly with from Portland to Jamaica? 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.
7.9
DeltaOverall score based on 8398 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

The flight was smooth, the crew was great but the plane was quite old

8.0 ExcellentDimitrina, Apr 2026
BOS - DCA
Read more Delta reviews

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It's a long flight and I would have liked better snacks between lunch and the arrival meal. It's fine to have fruit and nuts but I really don't like ramen because it's salty junk soup. I'd suggest sandwiches. They're not expensive nor are they hard to store for a long flight. The FA's had a couple of big services and they were super busy preparing, executing and then cleaning up. Then they disappeared.

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

This was the first flight in the morning. We boarded fine. The cabin door was closed and we were ready to go. We were notified by the Captain that ATC issued and ground stop for 40 minutes. So, without even pushing back from the gate, we were already 40 minutes late. We actually were released to push-back and taxi at 30 minutes. But, some passengers had tight connections and were not going to make their connections. Some passengers asked about the delay and the effect on the connections and were told by the cabin attendant that all flights will be delayed and so they should be OK. However, that was not true. My connecting flight was on time and I arrived at IAH with 21 minutes to make my connection. I did and I'm happy about that, but the flight crew should not have given assurances to the passengers who might have missed their connections.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

All good flight was 35 minutes early when arriving in Edinburgh

Flights were on time actually early service was good and crew cheerful

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

Air condition was not working for long both after boarding and also after landing ; unbearably hot and suffocating

On time flight, good communication about boarding, lines didn't form unnecessarily for boarding before their group was announced (kept aisles clear), friendly flight attendants and service

Flight was extremely hot and they made us check our bags when the space was nowhere near full

Everything was excellent and I enjoyed myself. Thank for everything

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Boarding was quick and efficient. We arrived at our destination early.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Everything you need to know for your flight from Portland to Jamaica

Information on your arrival and departure airports