$178 Find Cheap Flights from Portland to Jamaica - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Jamaica

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Montego Bay
6h 17m2 stops
from $409per person
Kingston
7h 06m2 stops
from $477per person
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?

The cheapest month for flights from Portland to Jamaica is May, when tickets cost $352 (return) on average. On the other hand, the most expensive months are February and September, when the average cost of round-trip tickets is $1,008 and $715 respectively.

Good to know

Low season

March

Cheapest flight

$178
Most popular time to fly with an average 12% 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 airlines flying 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.
7.4
United AirlinesOverall score based on 10226 reviews
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
6.7Food
Airline reviews

United did nit provide any updated on flight crew not bein available until boarding time started. It was bad. Itws alate night flight and there no proactive communication and iha d an important meeting that i missed due to thus

2.0 MediocreMadhavan, Sep 2026
Read more United Airlines reviews

United did nit provide any updated on flight crew not bein available until boarding time started. It was bad. Itws alate night flight and there no proactive communication and iha d an important meeting that i missed due to thus

From the boarding crew to the FAs was such a good team. All with smiles and positive energy. The pilots made an announcement of us waiting on some passengers who were late landing and I didn’t hear one person feel like it was an inconvenience which was wonderful. Massive kudos to all that worked that flight. Everyone was united. 😊💙

Smooth flight, easy boarding process. Made up time in the air with initial delay due to weather pass through

Flight was over two hours late, but they notified us early in the morning. They ended up changing planes the food on board that was extremely mediocre and we were in premier class.

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

I enjoyed it, again I believe air Canada has better seating options and better drink options

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

Why is it that United flights from Newark are constantly delayed? Newark is a United hub!!!!!

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

I sat in seat 22D near the back right of the plane. My phone battery was getting low, so I plugged my charger into the power outlets below the seats in front of me. They did not work. When I asked the flight attendant whether this was the case for the whole plane he said, "No. It's only this one. It hasn't worked for months". This should be noted to whomever services this plane so that maintenance can fix this for future passengers. I was on Flight AA5614 from Grand Rapids to Philadelphia on Wednesday, September 23, 2026.

The crew was wonderful, the plane was fine. We left the gate on time, but we had to wait 40 minutes on the tarmac because of all the congestion at Boston.

Seats were the worst i ever experienced — narrow, hard, no leg room and a long flight

ontime. Seats are terribly close together for someone my height.

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Nothing exceptional. No drink of any type, even in first class was provided for the hour and half trip.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

More options for your flight from Portland to Jamaica

Complete your trip to Jamaica with a hotel stay or car rental