$247+ Cheap flights from Winnipeg (YWG) to Portland (PDX)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Nov 15 — Nov 221
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Winnipeg to Portland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Winnipeg to Portland
Cheapest
Best
Last-minute
One-way
Cheapest flights from Winnipeg to PortlandExplore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2026.
Explore the most affordable flight options available from Winnipeg to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2026.
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:54 pm -
1 stop9h 25m
Mon 12/146:00 am -
1 stop9h 34m
Deal found 10/15![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:32 pm -
1 stop7h 14m
Mon 11/2311:58 am -
1 stop10h 35m
Deal found 10/13![Delta logo]()
$484
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:32 pm -
1 stop7h 14m
Fri 11/2011:58 am -
1 stop10h 35m
Deal found 10/16![Delta logo]()
$517
This Air Canada deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:40 am -
1 stop4h 46m
Mon 12/143:15 pm -
1 stop8h 17m
Deal found 10/14![Air Canada logo]()
$519
This Air Canada deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:40 am -
1 stop4h 46m
Fri 12/43:15 pm -
1 stop8h 17m
Deal found 10/13![Air Canada logo]()
$520
Best flights from Winnipeg to PortlandDiscover carefully curated flight deals from Winnipeg to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 16, 2026.
Discover carefully curated flight deals from Winnipeg to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 16, 2026.
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:54 pm -
1 stop9h 25m
Mon 12/146:00 am -
1 stop9h 34m
Deal found 10/15![Delta logo]()
$439
This Air Canada deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/56:40 am -
1 stop4h 46m
Mon 12/143:15 pm -
1 stop8h 17m
Deal found 10/14![Air Canada logo]()
$519
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:32 pm -
1 stop7h 14m
Mon 11/235:51 pm -
2 stops17h 04m
Deal found 10/13![Delta logo]()
$506
This Air Canada deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:40 am -
1 stop4h 46m
Fri 12/43:15 pm -
1 stop8h 17m
Deal found 10/13![Air Canada logo]()
$520
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:32 pm -
1 stop7h 14m
Fri 11/2011:58 am -
1 stop10h 35m
Deal found 10/16![Delta logo]()
$517
This Air Canada deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:40 am -
1 stop4h 46m
Tue 11/103:15 pm -
1 stop8h 17m
Deal found 10/13![Air Canada logo]()
$541
Last-minute flights from Winnipeg to PortlandDiscover last-minute flight deals from Winnipeg to Portland. Data last updated October 16, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Portland. Data last updated October 16, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:40 am -
1 stop4h 46m
Tue 11/103:15 pm -
1 stop8h 17m
Deal found 10/13![Air Canada logo]()
$541
This Air Canada deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:40 am -
1 stop4h 46m
Fri 11/133:15 pm -
1 stop8h 17m
Deal found 10/14![Air Canada logo]()
$547
This United deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/93:15 pm -
2 stops21h 03m
Fri 11/133:15 pm -
2 stops8h 04m
Deal found 10/14![Multiple Airlines logo]()
$573
This Air Canada deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:05 pm -
2 stops15h 21m
Fri 11/203:15 pm -
1 stop8h 17m
Deal found 10/14![Air Canada logo]()
$563
This Delta deal was found by Cheapflights users on 10/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/116:32 pm -
1 stop7h 14m
Fri 11/2011:58 am -
1 stop10h 35m
Deal found 10/14![Delta logo]()
$574
This Delta deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/136:32 pm -
1 stop7h 14m
Fri 11/2011:58 am -
1 stop10h 35m
Deal found 10/16![Delta logo]()
$517
This United Airlines deal was found by Cheapflights users on 10/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/133:15 pm -
2 stops20h 21m
Fri 11/203:40 pm -
2 stops19h 43m
Deal found 10/16![United Airlines logo]()
$543
This Delta deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:32 pm -
1 stop7h 14m
Mon 11/2311:58 am -
1 stop10h 35m
Deal found 10/13![Delta logo]()
$484
This Air Canada deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:40 am -
1 stop4h 46m
Fri 12/43:15 pm -
1 stop8h 17m
Deal found 10/13![Air Canada logo]()
$520
One-way flights from Winnipeg to PortlandSearch for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated October 16, 2026.
Search for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated October 16, 2026.
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:32 pm -
1 stop7h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$247
This Air Canada deal was found by Cheapflights users on 10/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:40 am -
1 stop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/12![Air Canada logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:00 am -
3 stops27h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Multiple Airlines logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 10/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/307:55 pm -
2 stops27h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/13![Multiple Airlines logo]()
$293
This Air Canada deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:40 am -
1 stop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Air Canada logo]()
$294
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/19:40 am -
1 stop15h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$298
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/163:15 pm -
2 stops20h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$303
This Delta deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2712:15 pm -
1 stop10h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![Delta logo]()
$313
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/309:40 am -
1 stop13h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 10/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/299:40 am -
2 stops28h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/15![United Airlines logo]()
$330
Find flight deals from Winnipeg to Portland
Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Portland (PDX). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 16, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $417 (Air Canada) |
One-way from | $247 (Delta) |
Popular in | October |
Cheapest in | June |
Average price | $583 |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 16, 2026.
Use the filters below to find and compare flights from Winnipeg to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Thu 11/26
6:40 am-8:26 am
1 stop4h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$257
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/16
10:00 am-10:07 am
3 stops27h 07m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$287
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/30
7:55 pm-8:52 pm
2 stops27h 57m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$293
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 1/1
9:40 am-10:26 pm
1 stop15h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$298
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/16
3:15 pm-8:36 am
2 stops20h 21m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$303
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sun 12/27
12:15 pm-7:39 pm
1 stop10h 24m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$313
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 11/30
6:40 am-8:26 am
1 stop4h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$333
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Tue 12/29
9:40 am-10:26 pm
1 stop15h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$333
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 12/28
12:15 pm-7:39 pm
1 stop10h 24m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$335
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 10/23
9:05 pm-11:02 pm
2 stops27h 57m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$358
Showing 1-10 of 17 resultsSorted by cheapest first
- Most accurate provider: When it comes to deals on Winnipeg-Portland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Portland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Portland flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Winnipeg-Portland flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Winnipeg-Portland flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Winnipeg to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Winnipeg with our price prediction graph.
YWG-PDX
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Winnipeg to Portland
Reviews of airlines servicing Portland
Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated October 16, 2026.
Peruse reviews from past customers who have flown with Air Canada from Winnipeg to Portland to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.3
Boarding
7.3
Crew
7.8
Overall
7.1
Entertainment
6.8
Comfort
7.1
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Food
6.3
Boarding
7.3
Crew
7.8
Overall
7.1
Entertainment
6.8
Comfort
7.1
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Related info for your journey
Find useful and relevant information for your journey from Winnipeg to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsBeaverton
Seaside
Durham
Longview
Lake Oswego
Cannon Beach
Vancouver
Kelso
Troutdale
Lincoln City
Clackamas
McMinnville
The Dalles
Wilsonville
Stevenson
Hillsboro
Tillamook
Astoria
Gresham
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Complete your trip
Flights by cabin class
Other flight options
Other flights from Winnipeg
Popular flights
Portland flight routes
Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Winnipeg to Portland by cabin class
Find flights from Winnipeg to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Portland flights
Browse other Winnipeg and Portland flight options. Last updated on October 16, 2026.
Other flights from Winnipeg
Browse through other flights departing from Winnipeg. Flights are based on user searches made on Cheapflights and were last updated on October 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 16, 2026.
Top airline flying from Winnipeg to Portland
Discover the top airline that operate flights from Winnipeg to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$345 | Average$503 | FlexibilityNo cancel fee | On-time67% |