Flights To Portland - Cheap Flights Starting at CA $186

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Portland's top cities

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.

Port Antonio

Flights
Port Antonio

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.

Fri, Oct 16 - Sun, Oct 25
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $424 Roundtrip, found 1 hour ago
CA $424
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Fri, Oct 16 from Pearson Intl. to Norman Manley Intl., returning Sun, Oct 25, priced at CA $424 found 1 hour ago
Fri, Sep 18 - Mon, Sep 21
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $518 Roundtrip, found 1 hour ago
CA $518
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Sep 18 from Pearson Intl. to Norman Manley Intl., returning Mon, Sep 21, priced at CA $518 found 1 hour ago
Tue, Oct 13 - Mon, Oct 19
JFK
John F. Kennedy Intl.
KIN
Norman Manley Intl.
CA $524 Roundtrip, found 1 day ago
CA $524
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 13 from John F. Kennedy Intl. to Norman Manley Intl., returning Mon, Oct 19, priced at CA $524 found 1 day ago
Mon, Sep 7 - Fri, Sep 11
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $529 Roundtrip, just found
CA $529
Roundtrip
just found
Select WestJet flight, departing Mon, Sep 7 from Pearson Intl. to Norman Manley Intl., returning Fri, Sep 11, priced at CA $529 just found
Thu, Oct 1 - Thu, Nov 26
YYZ
Pearson Intl.
KIN
Norman Manley Intl.
CA $541 Roundtrip, found 3 days ago
CA $541
Roundtrip
found 3 days ago
Select Air Canada flight, departing Thu, Oct 1 from Pearson Intl. to Norman Manley Intl., returning Thu, Nov 26, priced at CA $541 found 3 days ago
Sat, Sep 12 - Mon, Sep 21
YOW
Macdonald-Cartier Intl.
KIN
Norman Manley Intl.
CA $575 Roundtrip, found 3 days ago
CA $575
Roundtrip
found 3 days ago
Select Air Canada flight, departing Sat, Sep 12 from Macdonald-Cartier Intl. to Norman Manley Intl., returning Mon, Sep 21, priced at CA $575 found 3 days ago
Thu, Oct 22 - Sun, Oct 25
FLL
Fort Lauderdale - Hollywood Intl.
KIN
Norman Manley Intl.
CA $578 Roundtrip, found 2 hours ago
CA $578
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Oct 22 from Fort Lauderdale - Hollywood Intl. to Norman Manley Intl., returning Sun, Oct 25, priced at CA $578 found 2 hours ago
Fri, Nov 13 - Tue, Dec 15
YUL
Pierre Elliott Trudeau Intl.
KIN
Norman Manley Intl.
CA $580 Roundtrip, found 5 days ago
CA $580
Roundtrip
found 5 days ago
Select WestJet flight, departing Fri, Nov 13 from Pierre Elliott Trudeau Intl. to Norman Manley Intl., returning Tue, Dec 15, priced at CA $580 found 5 days ago
Mon, Jan 25 - Mon, Feb 1
EWR
Newark Liberty Intl. Airport
KIN
Norman Manley Intl.
CA $601 Roundtrip, found 6 days ago
CA $601
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Jan 25 from Newark Liberty Intl. Airport to Norman Manley Intl., returning Mon, Feb 1, priced at CA $601 found 6 days ago
OriginDestinationTravel datesFlights from*
YYZKingstonOctober 19 to November 5CA $416
JFKKingstonOctober 13 to October 19CA $524
JFKKingstonOctober 13 to October 19CA $524
FLLKingstonOctober 22 to October 25CA $578
MIAKingstonNovember 7 to November 14CA $587
ATLKingstonOctober 25 to November 5CA $661
BOSKingstonOctober 2 to October 5CA $662
MCOKingstonOctober 5 to October 10CA $663
NASKingstonNovember 24 to November 30CA $941
POSKingstonSeptember 7 to September 14CA $968
YYZBoscobelOctober 14 to October 21CA $1,150
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
JFKKingstonAugust 28 to September 6CA $790
JFKKingstonAugust 28 to September 6CA $790
MIAKingstonAugust 29 to September 17CA $859
FLLKingstonAugust 28 to October 9CA $888
ATLKingstonAugust 29 to September 2CA $1,000
YYZKingstonAugust 28 to September 2CA $1,157
*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

Sep 4 - Sep 10

6 night stay

Toronto (YTO) to Ocho Rios (OCJ)

WestJet • Coach

Ocho Rios (OCJ) to Toronto (YTO)

American Airlines • Coach
Price was CA $4,321, price is now CA $3,662 per person
CA $3,662
per person
found 6 hours ago
Don't see what you're looking for?
See all available trips from Toronto to Portland
View all trips

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.
8/10 Very good! (227 reviews)
"The stay was amazing. The views from the room, the sound of waves crashing at night was so refreshing. The quiet of the property really allows for reset, relaxation and reconnection that a hotel can’t provide. The staff were helpful and respectful at all times, zero complaints. Nitpicking - I wished ..."

Reviewed on Aug 22, 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 Blue Lagoon and Trident Castle are located nearby.
Opens in a new windowJamaica Palace Hotel
Match Resort Hotel

Match Resort Hotel

3 out of 5
Dolphin Bay Port Antonio
Stay at this hotel in Port Antonio. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Blue Lagoon and Trident Castle are located nearby.
8/10 Very good! (240 reviews)
"Didn’t like the fact the room had no mirro."

Reviewed on Aug 22, 2026

Opens in a new windowMatch Resort Hotel
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 Blue Lagoon and Frenchman's Cove Beach are located nearby.
Opens in a new windowGeejam
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 $416 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?
October 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 $416. 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 $416 and CA $1,157 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.