Flights To Portland - Cheap Flights Starting at CA $188

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Epic view of the sun as it sets in Montego Bay, Jamaica.

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How Much Does it Cost To Fly To Portland?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Mon, Jun 15 - Mon, Jun 22
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $469 Roundtrip, found 5 hours ago
CA $469
Roundtrip
found 5 hours ago
Select Flair Airlines flight, departing Mon, Jun 15 from Pearson Intl. to Norman Manley Intl., returning Mon, Jun 22, priced at CA $469 found 5 hours ago
Fri, Dec 4 - Wed, Dec 16
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $524 Roundtrip, found 1 day ago
CA $524
Roundtrip
found 1 day ago
Select Air Canada flight, departing Fri, Dec 4 from Pearson Intl. to Norman Manley Intl., returning Wed, Dec 16, priced at CA $524 found 1 day ago
Fri, Jul 3 - Fri, Jul 10
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $562 Roundtrip, found 1 day ago
CA $562
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Jul 3 from Pearson Intl. to Norman Manley Intl., returning Fri, Jul 10, priced at CA $562 found 1 day ago
Tue, Jul 14 - Tue, Jul 21
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $572 Roundtrip, found 5 days ago
CA $572
Roundtrip
found 5 days ago
Select WestJet flight, departing Tue, Jul 14 from Pearson Intl. to Norman Manley Intl., returning Tue, Jul 21, priced at CA $572 found 5 days ago
Thu, May 28 - Mon, Jun 1
YKF
Region of Waterloo Intl.
KIN
Norman Manley Intl.
CA $591 Roundtrip, found 1 day ago
CA $591
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, May 28 from Region of Waterloo Intl. to Norman Manley Intl., returning Mon, Jun 1, priced at CA $591 found 1 day ago
Sun, Jun 7 - Tue, Jun 16
YHZ
Stanfield Intl.
KIN
Norman Manley Intl.
CA $601 Roundtrip, found 3 days ago
CA $601
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sun, Jun 7 from Stanfield Intl. to Norman Manley Intl., returning Tue, Jun 16, priced at CA $601 found 3 days ago
Wed, Jun 17 - Thu, Jun 18
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $606 Roundtrip, found 5 days ago
CA $606
Roundtrip
found 5 days ago
Select Caribbean Airlines flight, departing Wed, Jun 17 from Pearson Intl. to Norman Manley Intl., returning Thu, Jun 18, priced at CA $606 found 5 days ago
Tue, Aug 25 - Tue, Sep 8
YHM
John C. Munro Hamilton Intl.
KIN
Norman Manley Intl.
CA $606 Roundtrip, found 2 days ago
CA $606
Roundtrip
found 2 days ago
Select Air Canada flight, departing Tue, Aug 25 from John C. Munro Hamilton Intl. to Norman Manley Intl., returning Tue, Sep 8, priced at CA $606 found 2 days ago
OriginDestinationTravel datesFlights from*
YYZKingstonJune 8 to June 15CA $484
JFKKingstonJuly 4 to July 28CA $552
EWRKingstonJuly 4 to July 28CA $552
ATLKingstonAugust 19 to September 2CA $599
FLLKingstonJuly 26 to August 30CA $643
BOSKingstonJuly 10 to July 17CA $675
MCOKingstonJune 21 to June 23CA $687
NASKingstonJune 12 to June 15CA $935
YYZBoscobelJune 7 to June 16CA $1,163
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
YYZKingstonMay 29 to June 5CA $525
FLLKingstonMay 29 to June 5CA $639
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa
3.0-star property

Blue Berry Hills Villa

Jul 25 - Aug 1

7 night stay

Toronto (YYZ) to Ocho Rios (OCJ)

WestJet • Roundtrip • Coach
Price was CA $5,074, price is now CA $4,182 per person
CA $4,182
per person
found 1 day ago
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Travelers ❤️ These Portland 🏨

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Stay at this hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located nearby.
8.2/10 Very Good! (198 reviews)
"It was"

Reviewed on May 20, 2026

Opens in a new windowSea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Book a stay at this business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Trident Castle and Frenchman's Cove Beach are located nearby.
8.2/10 Very Good! (302 reviews)
"I have stay here before and was very happy they could accommodate my family and I.. We booked another accommodation which was not as advertised… Breakfast is on point and with a wide choice. Room was clean and smells clean too… Great location to pop into town or to Boston beach… I will be back.."

Reviewed on May 19, 2026

Opens in a new windowJamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
Book a stay at this luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Frenchman's Cove Beach and San San Beach are located nearby.
9.6/10 Exceptional! (89 reviews)
"Property and scenery was great . Awesome staff. Room and bathroom well decorated with pictures of music musicians in black and white also country folks. Food was delicious also property , pools and surroundings is well kept ."

Reviewed on May 14, 2026

Opens in a new windowGeejam
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Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
Book a stay at this beach resort in Port Antonio. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Boston Bay Beach and Winnifred Beach are located nearby.
9.2/10 Wonderful! (222 reviews)
"My family and I spent one night over our 4 day adventure in Portland. Our first time experiencing an eco-tourism type of accommodation. It was amazing. We stayed in the Fig Tree hut and all I can say is it is the best room of the house. They are undergoing some renovation but no disruption to our ..."

Reviewed on May 21, 2026

Opens in a new windowGreat Huts
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Portland?
In the last seven days, the cheapest roundtrip flight to Portland cost CA $469 on this site. Take a look at our fantastic deals, make a booking and look forward to your next travel adventure. This price was available on Travelocity for flights to Portland departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Portland?
June is the cheapest month to fly to Portland based on Travelocity's direct return flight demand between January and December last year. We can help you snap up a great bargain so you can start organizing your escape today.
How can I check my flight status to Portland?
Whether you'd like to check the status of your flight to Portland or change your itinerary, you'll find all the info you need on our customer portal, Trips. Click on "Trips" at the top of the Travelocity homepage, then log in or create a new account. Another helpful way to view and manage all your bookings is with the Travelocity app. Get alerts about gate changes or flight delays and share updates with any friends or family flying with you.
How do I find the best deals on flights to Portland?
Be flexible with your dates and you might just find an incredible deal. When searching for flights on Travelocity, select the "Flexible dates" box at the top of the page to see all the prices for surrounding days. Also try to book early and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Portland was CA $469. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Portland with Travelocity?
A memorable vacation is at the click of a button when you book your trip with Travelocity. With great deals on cheap family flights, accommodations and more, we make it simple to find awesome prices to suit your needs. You can also make use of our 24/7 online chat support and free cancellations on most hotels during every stage of the process. Wander wisely with us and reserve your cheap flights to Portland today.
What are the most popular flight routes to Portland?
Browse through these busy flight routes to Portland and start planning your next great adventure:

  • New York, NY (JFK-John F. Kennedy Intl.) to Norman Manley Intl. Airport (KIN) - 749 flights a month.
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to Norman Manley Intl. Airport (KIN) - 706 flights a month.
  • Providenciales (PLS-Providenciales Intl.) to Norman Manley Intl. Airport (KIN) - 212 flights a month.

How much is a flight to Portland on average?
Airfares for roundtrip flights to Portland cost between CA $469 and CA $1,163 in the last seven days. The moment you see a terrific deal, lock it in and get ready to take off on your next fun adventure with Travelocity. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.