$152 Find Cheap Flights from Portland to Jamaica

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to Jamaica departing on 7/15. 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 Bay1 stop$352
Kingston
Kingston2 stops$565
Montego Bay
Montego Bay1 stop$352
Kingston
Kingston2 stops$565

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

Wed, Aug 26 - Wed, Sep 2
Delta Logo
6:05 am - 3:34 pm
PWM
-
MBJ
10h 29m
1 stop
Delta Logo
2:26 pm - 11:13 pm
MBJ
-
PWM
7h 47m
1 stop
$352Delta
Wed, Aug 26 - Wed, Sep 2
Delta Logo
6:30 am - 3:34 pm
PWM
-
MBJ
10h 04m
2 stops
Delta Logo
1:09 pm - 11:13 pm
MBJ
-
PWM
9h 04m
1 stop
$357Delta
Tue, Aug 18 - Sun, Aug 23
American Airlines Logo
6:46 pm - 11:37 am
PWM
-
MBJ
17h 51m
2 stops
American Airlines Logo
5:08 pm - 2:21 pm
MBJ
-
PWM
20h 13m
2 stops
$362American Airlines
Tue, Aug 18 - Sun, Aug 23
American Airlines Logo
7:22 am - 1:28 pm
PWM
-
MBJ
7h 06m
1 stop
American Airlines Logo
2:12 pm - 11:38 am
MBJ
-
PWM
20h 26m
1 stop
$364American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
7:22 am - 1:28 pm
PWM
-
MBJ
7h 06m
1 stop
American Airlines Logo
5:08 pm - 2:21 pm
MBJ
-
PWM
20h 13m
2 stops
$367American Airlines
Wed, Aug 19 - Sun, Aug 23
American Airlines Logo
7:22 am - 1:28 pm
PWM
-
MBJ
7h 06m
1 stop
American Airlines Logo
2:12 pm - 11:38 am
MBJ
-
PWM
20h 26m
1 stop
$369American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
6:50 pm - 11:00 am
PWM
-
MBJ
17h 10m
2 stops
American Airlines Logo
5:00 pm - 1:22 pm
MBJ
-
PWM
19h 22m
2 stops
$411American Airlines
Sat, Jul 18 - Tue, Jul 21
United Airlines Logo
5:15 am - 3:10 pm
PWM
-
MBJ
10h 55m
1 stop
United Airlines Logo
4:12 pm - 11:51 pm
MBJ
-
PWM
6h 39m
1 stop
$437United Airlines
Sun, Jul 19 - Mon, Jul 20
JetBlue Logo
6:00 am - 6:48 pm
PWM
-
KIN
13h 48m
1 stop
JetBlue Logo
7:00 am - 12:30 pm
KIN
-
PWM
28h 30m
2 stops
$795JetBlue
Sun, Jul 19 - Mon, Jul 20
JetBlue Logo
6:00 am - 6:48 pm
PWM
-
KIN
13h 48m
1 stop
JetBlue Logo
8:10 pm - 12:30 pm
KIN
-
PWM
15h 20m
1 stop
$814JetBlue
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.

What is the cheapest month to fly from Portland to Jamaica?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Jamaica, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Jamaica is September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are March and July, when the average cost of round-trip tickets is $634 and $559 respectively.

Good to know

Low seasonMay
Cheapest flight$152
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 15% 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 8425 reviews
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
7.8Comfort
Airline reviews

Planes were clean, no water or snacks on either flight.

6.0 GoodAnonymous, May 2026
ECP - ATL
Read more Delta reviews

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

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

Information on your arrival and departure airports