$235+ Cheap flights from Winnipeg (YWG) to Oregon
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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Nov 8 — Nov 151
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Oregon with Cheapflights
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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
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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 Oregon
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Cheapest flights from Winnipeg to OregonExplore the most affordable flight options available from Winnipeg to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 9, 2026.
Explore the most affordable flight options available from Winnipeg to Oregon. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 9, 2026.
This Air Canada deal was found by Cheapflights users on 10/7. 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.
Sun 10/255:40 am -
1 stop5h 46m
Mon 11/93:15 pm -
1 stop8h 17m
Deal found 10/7![Air Canada logo]()
$395
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/1811:55 am -
1 stop4h 46m
Wed 11/253:15 pm -
1 stop8h 17m
Deal found 10/4![Air Canada logo]()
$417
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/146:40 am -
1 stop4h 46m
Mon 11/233:15 pm -
2 stops7h 54m
Deal found 10/4![Air Canada logo]()
$421
This Delta deal was found by Cheapflights users on 10/7. 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
Sun 11/2212:35 am -
1 stop10h 20m
Deal found 10/7![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 10/5. 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.
Thu 10/225:40 pm -
1 stop8h 04m
Mon 10/2611:51 am -
1 stop9h 28m
Deal found 10/5![Delta logo]()
$428
This United Airlines deal was found by Cheapflights users on 10/8. 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.
Sat 12/58:40 am -
1 stop11h 27m
Mon 12/147:25 pm -
2 stops14h 58m
Deal found 10/8![United Airlines logo]()
$442
This Air Canada deal was found by Cheapflights users on 10/6. 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 11/116:40 am -
1 stop4h 46m
Fri 11/203:15 pm -
1 stop8h 17m
Deal found 10/6![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 10/7. 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 11/216:40 am -
1 stop4h 46m
Sat 11/283:15 pm -
2 stops7h 54m
Deal found 10/7![Air Canada logo]()
$447
This Air Canada deal was found by Cheapflights users on 10/8. 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 12/711:55 am -
1 stop4h 46m
Tue 12/153:15 pm -
2 stops8h 09m
Deal found 10/8![Air Canada logo]()
$449
Best flights from Winnipeg to OregonDiscover carefully curated flight deals from Winnipeg to Oregon that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
Discover carefully curated flight deals from Winnipeg to Oregon that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 9, 2026.
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/1811:55 am -
1 stop4h 46m
Wed 11/253:15 pm -
1 stop8h 17m
Deal found 10/4![Air Canada logo]()
$417
This Delta deal was found by Cheapflights users on 10/7. 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
Sun 11/2212:35 am -
1 stop10h 20m
Deal found 10/7![Delta logo]()
$427
This United Airlines deal was found by Cheapflights users on 10/7. 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.
Thu 10/222:00 pm -
1 stop10h 23m
Mon 10/267:26 pm -
2 stops14h 57m
Deal found 10/7![United Airlines logo]()
$465
This United deal was found by Cheapflights users on 10/5. 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.
Sat 1/97:00 am -
2 stops16h 15m
Sat 1/163:15 pm -
2 stops7h 54m
Deal found 10/5![Multiple Airlines logo]()
$503
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/146:40 am -
1 stop4h 46m
Mon 11/233:15 pm -
1 stop8h 17m
Deal found 10/4![Air Canada logo]()
$421
This Delta deal was found by Cheapflights users on 10/7. 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 11/216:32 pm -
1 stop7h 14m
Sat 11/286:00 am -
1 stop9h 42m
Deal found 10/7![Delta logo]()
$427
This Delta deal was found by Cheapflights users on 10/5. 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.
Thu 10/225:40 pm -
1 stop8h 04m
Mon 10/2611:51 am -
1 stop9h 28m
Deal found 10/5![Delta logo]()
$428
This Air Canada deal was found by Cheapflights users on 10/6. 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 11/116:40 am -
1 stop4h 46m
Fri 11/203:15 pm -
2 stops7h 54m
Deal found 10/6![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 10/6. 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 10/225:45 am -
1 stop5h 46m
Mon 10/263:20 pm -
1 stop7h 12m
Deal found 10/6![Air Canada logo]()
$462
This Air Canada deal was found by Cheapflights users on 10/7. 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 11/2111:55 am -
2 stops11h 07m
Sat 11/283:15 pm -
2 stops7h 54m
Deal found 10/7![Air Canada logo]()
$525
Last-minute flights from Winnipeg to OregonDiscover last-minute flight deals from Winnipeg to Oregon. Data last updated October 9, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Oregon. Data last updated October 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/5. 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.
Thu 10/225:40 pm -
1 stop8h 04m
Mon 10/2611:51 am -
1 stop9h 28m
Deal found 10/5![Delta logo]()
$428
This Air Canada deal was found by Cheapflights users on 10/6. 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 10/225:45 am -
1 stop5h 46m
Mon 10/263:20 pm -
1 stop7h 12m
Deal found 10/6![Air Canada logo]()
$462
This Air Canada deal was found by Cheapflights users on 10/7. 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.
Sun 10/255:40 am -
1 stop5h 46m
Mon 11/93:15 pm -
1 stop8h 17m
Deal found 10/7![Air Canada logo]()
$395
This Air Canada deal was found by Cheapflights users on 10/6. 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 11/116:40 am -
1 stop4h 46m
Fri 11/203:15 pm -
1 stop8h 17m
Deal found 10/6![Air Canada logo]()
$444
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/146:40 am -
1 stop4h 46m
Mon 11/233:15 pm -
2 stops7h 54m
Deal found 10/4![Air Canada logo]()
$421
This Delta deal was found by Cheapflights users on 10/7. 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
Sun 11/2212:35 am -
1 stop10h 20m
Deal found 10/7![Delta logo]()
$427
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/1811:55 am -
1 stop4h 46m
Wed 11/253:15 pm -
1 stop8h 17m
Deal found 10/4![Air Canada logo]()
$417
This Air Canada deal was found by Cheapflights users on 10/7. 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 11/216:40 am -
1 stop4h 46m
Sat 11/283:15 pm -
2 stops7h 54m
Deal found 10/7![Air Canada logo]()
$447
One-way flights from Winnipeg to OregonSearch for one-way flight options from Winnipeg to Oregon. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
Search for one-way flight options from Winnipeg to Oregon. Find affordable one-way fares based on user searches. Data last updated October 9, 2026.
This Air Canada deal was found by Cheapflights users on 10/4. 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 11/186:40 am -
1 stop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![Air Canada logo]()
$235
This Air Canada deal was found by Cheapflights users on 10/6. 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 11/209:10 am -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Air Canada logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/6. 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.
Fri 11/204:45 pm -
2 stops18h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$277
This United Airlines deal was found by Cheapflights users on 10/4. 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 11/182:15 pm -
2 stops10h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/4![United Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 10/5. 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.
Wed 11/184:45 pm -
2 stops20h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/5![Multiple Airlines logo]()
$280
This Mytrip deal was found by Cheapflights users on 10/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:00 pm -
2 stops21h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Multiple Airlines logo]()
$315
Find flight deals from Winnipeg to Oregon
Keep the following information in mind while searching for Winnipeg to Oregon flight deals. Data was last updated October 9, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $395 (Air Canada) |
One-way from | $235 (Air Canada) |
Popular in | December |
Cheapest in | June |
Average price | $460 |
Cheapflights Fare Finder
Customize your flight search to find flights from Winnipeg to Oregon 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 9, 2026.
Use the filters below to find and compare flights from Winnipeg to Oregon 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
Wed 11/18
6:40 am-8:26 am
1 stop4h 46m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$235
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 11/20
9:10 am-1:41 pm
1 stop7h 31m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$247
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 11/20
4:45 pm-8:32 am
2 stops18h 47m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$277
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 11/18
2:15 pm-10:09 pm
2 stops10h 54m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$279
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 11/18
4:45 pm-10:36 am
2 stops20h 51m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$280
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 10/26
4:00 pm-11:07 am
2 stops21h 07m
Portland
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$315
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 11/18
11:55 am-1:41 pm
1 stop4h 46m
Portland
Wed 11/25
3:15 pm-2:32 am
1 stop8h 17m
$417
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 11/14
6:40 am-8:26 am
1 stop4h 46m
Portland
Mon 11/23
3:15 pm-2:32 am
1 stop8h 17m
$421
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 11/14
6:32 pm-10:46 pm
1 stop7h 14m
Portland
Sun 11/22
12:35 am-1:55 pm
1 stop10h 20m
$427
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Sat 11/21
6:32 pm-10:46 pm
1 stop7h 14m
Portland
Sat 11/28
6:00 am-6:42 pm
1 stop9h 42m
$427
Showing 1-10 of 16 resultsSorted by cheapest first
Best time to book a flight from Winnipeg to Oregon
Have a flexible travel schedule? Discover the best time to fly to Oregon 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 Oregon
YWG-USOR
YWG-PDX
What is the cheapest month to book a flight from Winnipeg to Oregon?
Currently, June is the cheapest month in which you can book a flight from Winnipeg to Oregon (average of $330). Flying from Winnipeg to Oregon in December is currently the most expensive (average of $539). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How much does it cost to fly round-trip from Winnipeg to Oregon?
Airfare is below average for this route at the moment.
Winnipeg to Oregon flights typically cost between $407 and $460 in October.The cheapest round-trip price found within the last 5 days was $395 on Air Canada (Oct 25-Nov 9).
Reviews of airlines servicing Oregon
Get insights into the airlines that provide service to Oregon. 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 Oregon. Reviews last updated October 9, 2026.
Read through reviews of airlines operating flights from Winnipeg to Oregon, such as Air Canada. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.3
Entertainment
6.8
Boarding
7.3
Overall
7.1
Comfort
7.1
Crew
7.8
Reviews
1 / 20
2.0
MediocreSylvia,Aug 2026
YYZ - PHL
Food
6.3
Entertainment
6.8
Boarding
7.3
Overall
7.1
Comfort
7.1
Crew
7.8
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 Oregon. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Winnipeg to Oregon
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Complete your trip
Complete your trip to Oregon by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Winnipeg to Oregon, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Winnipeg and Oregon flights
Browse other Winnipeg and Oregon flight options. Last updated on October 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Winnipeg to Oregon
Discover the top airline that operate flights from Winnipeg to Oregon. 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 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$345 | Average$503 | FlexibilityNo cancel fee | On-time67% |