A clear turquoise sea, a small island with dense green foliage, and a clear blue sky.

Portland Flights - Book Cheap Flights to Portland

View RM913 flight on Tue, 8 Sept 2026Opens in a new window

Flight 1

Flight 2

Popular airlines to Portland

  • American Airlines

  • JetBlue Airways

  • Delta

  • United

  • Copa

  • Air Canada

  • Caribbean Airlines

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Portland

Prices were available within the past 7 days and start at RM913 for one-way flights and RM2,193 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, 8 Sept - Tue, 15 Sept
ORD
Chicago
KIN
Kingston
RM2,193 Return, found 2 days ago
RM2,193
Return
found 2 days ago
Select Delta flight, departing Tue, 8 Sept from Chicago to Kingston, returning Tue, 15 Sept, priced at RM2,193 found 2 days ago
American Airlines
Wed, 9 Sept - Wed, 16 Sept
ORD
Chicago
KIN
Kingston
RM2,229 Return, found 15 hours ago
RM2,229
Return
found 15 hours ago
Select American Airlines flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,229 found 15 hours ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
KIN
Kingston
RM2,233 Return, found 15 hours ago
RM2,233
Return
found 15 hours ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,233 found 15 hours ago
Delta
Tue, 8 Sept - Tue, 15 Sept
ORD
Chicago
KIN
Kingston
RM2,318 Return, found 2 days ago
RM2,318
Return
found 2 days ago
Select Delta flight, departing Tue, 8 Sept from Chicago to Kingston, returning Tue, 15 Sept, priced at RM2,318 found 2 days ago
Delta
Wed, 9 Sept - Wed, 16 Sept
ORD
Chicago
KIN
Kingston
RM2,341 Return, found 15 hours ago
RM2,341
Return
found 15 hours ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,341 found 15 hours ago
Air Canada
Wed, 9 Sept - Wed, 16 Sept
ORD
Chicago
KIN
Kingston
RM2,345 Return, found 15 hours ago
RM2,345
Return
found 15 hours ago
Select Air Canada flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,345 found 15 hours ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
KIN
Kingston
RM2,381 Return, found 15 hours ago
RM2,381
Return
found 15 hours ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,381 found 15 hours ago
Delta
Wed, 9 Sept - Wed, 16 Sept
MDW
Chicago
KIN
Kingston
RM2,398 Return, found 15 hours ago
RM2,398
Return
found 15 hours ago
Select Delta flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,398 found 15 hours ago
Copa
Wed, 9 Sept - Wed, 16 Sept
ORD
Chicago
KIN
Kingston
RM2,422 Return, found 15 hours ago
RM2,422
Return
found 15 hours ago
Select Copa flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,422 found 15 hours ago
United
Wed, 9 Sept - Wed, 16 Sept
ORD
Chicago
KIN
Kingston
RM2,760 Return, found 15 hours ago
RM2,760
Return
found 15 hours ago
Select United flight, departing Wed, 9 Sept from Chicago to Kingston, returning Wed, 16 Sept, priced at RM2,760 found 15 hours ago

Frequently asked questions

How do I find cheap flights to Portland that have flexible change policies?
When it comes to flying these days, flexibility is important. That's why we've added a "No change fee" filter to help you locate flexible and cheap flights to Portland. It's on the left-hand side of your screen directly below the "Flexible change policies" subheading.
Which airlines fly to Portland?
Reserve your seat with one of these airlines and the exciting region of Portland will be all yours to discover:

  • JetBlue Airways - 151 flights to or near Portland each month, including 151 flights to Norman Manley Intl. Airport (KIN) per month.
  • American Airlines - 91 flights to or near Portland each month, including 91 flights to Norman Manley Intl. Airport (KIN) per month.
  • Spirit Airlines - 30 flights to or near Portland each month, including 30 flights to Norman Manley Intl. Airport (KIN) per month.

How can I find cheap tickets to Portland?
One of the easiest ways to nab cheap tickets to Portland is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll reveal the cheapest prices for nearby days. The lowest price for a flight to Portland in the last seven days was RM2,193. Booking ahead will generally help you pick up an even better deal.
How much is a flight to Portland?
You could have snapped up a return airfare to Portland from anywhere between RM2,193 and RM2,760 in the last seven days. For one-way trips departing from Chicago (ORD), the lowest amount paid during this time was just RM913.
What are the most popular airports to fly into in Portland?
Start arranging your Portland getaway by reserving a seat on one of the 338 flights each month to Norman Manley Intl. Airport (KIN). This is the region's principal gateway.
How much is a plane ticket to Portland?
In the last seven days, plane tickets cost between RM2,193 and RM2,760. Check out our awesome deals to Portland, pick your favourite and then start packing!
What months are the cheapest to book a flight to Portland?
The top month to book well-priced airfares to Portland is February. It's worth noting that in the USA, an expensive time to secure a ticket is the busy month of December.

Book with confidence

About Portland

Expedia offers flights to Portland to meet every traveler's needs. Whatever your flight need - Expedia has the flight for you. So choose from flights to Portland or destinations around the world and discover how easy it is to make your flight reservations on Expedia.
About Portland
*Available to Expedia members.