$122+ Cheap flights from Winnipeg (YWG) to Oregon
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Winnipeg to Oregon 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
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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 August 21, 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 August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am -
2 stops9h 50m
Tue 9/82:30 pm -
1 stop5h 40m
Deal found 8/16![WestJet logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:10 am -
1 stop5h 40m
Tue 9/82:30 pm -
1 stop5h 40m
Deal found 8/16![WestJet logo]()
$217
This FlightHub deal was found by Cheapflights users on 8/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/313:15 pm -
2 stops24h 35m
Tue 9/82:30 pm -
1 stop24h 55m
Deal found 8/16![WestJet logo]()
$271
This Delta deal was found by Cheapflights users on 8/17. 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 8/285:42 pm -
1 stop7h 38m
Sun 8/3012:35 am -
1 stop9h 19m
Deal found 8/17![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 8/20. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 8/20![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 8/16. 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.
Tue 9/296:40 am -
1 stop6h 09m
Sun 10/412:25 am -
1 stop9h 26m
Deal found 8/16![Delta logo]()
$300
This Delta deal was found by Cheapflights users on 8/20. 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 9/3012:41 pm -
1 stop9h 35m
Sat 10/1011:51 am -
1 stop9h 28m
Deal found 8/20![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 8/19. 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.
Tue 12/812:38 pm -
2 stops12h 49m
Sat 12/126:00 am -
2 stops8h 44m
Deal found 8/19![Delta logo]()
$513
This Delta deal was found by Cheapflights users on 8/20. 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.
Tue 9/153:58 pm -
2 stops9h 19m
Tue 9/225:29 pm -
2 stops16h 22m
Deal found 8/20![Delta logo]()
$526
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:50 pm -
3 stops13h 09m
Tue 9/2210:29 am -
2 stops28h 56m
Deal found 8/20![Multiple Airlines logo]()
$533
This Delta deal was found by Cheapflights users on 8/20. 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 12/1212:38 pm -
2 stops12h 49m
Tue 12/155:27 pm -
2 stops16h 27m
Deal found 8/20![Delta logo]()
$553
This United Airlines deal was found by Cheapflights users on 8/18. 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 12/88:30 am -
1 stop6h 39m
Sat 12/1212:45 pm -
1 stop6h 03m
Deal found 8/18![United Airlines logo]()
$674
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 August 21, 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 August 21, 2026.
This Delta deal was found by Cheapflights users on 8/17. 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 8/285:42 pm -
1 stop7h 38m
Sun 8/3012:35 am -
1 stop9h 19m
Deal found 8/17![Delta logo]()
$288
This Air Canada deal was found by Cheapflights users on 8/18. 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.
Tue 10/2710:55 am -
1 stop5h 46m
Sat 10/3110:00 am -
2 stops12h 09m
Deal found 8/18![Air Canada logo]()
$360
This United deal was found by Cheapflights users on 8/18. 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.
Fri 9/187:00 am -
2 stops19h 37m
Sun 9/207:45 pm -
1 stop5h 12m
Deal found 8/18![Multiple Airlines logo]()
$366
This United Airlines deal was found by Cheapflights users on 8/17. 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 9/308:45 am -
1 stop16h 08m
Sat 10/104:07 pm -
2 stops18h 30m
Deal found 8/17![United Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 8/16. 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.
Wed 9/25:42 pm -
1 stop7h 38m
Tue 9/812:25 am -
1 stop9h 26m
Deal found 8/16![Delta logo]()
$288
This Delta deal was found by Cheapflights users on 8/20. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 8/20![Delta logo]()
$289
This Air Canada deal was found by Cheapflights users on 8/18. 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 9/185:45 am -
1 stop5h 46m
Sun 9/207:45 pm -
1 stop5h 12m
Deal found 8/18![Air Canada logo]()
$361
This Delta deal was found by Cheapflights users on 8/17. 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 9/3012:41 pm -
1 stop9h 35m
Sat 10/103:00 pm -
1 stop6h 19m
Deal found 8/17![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/16. 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.
Mon 8/318:45 am -
2 stops14h 14m
Wed 9/911:02 pm -
1 stop10h 50m
Deal found 8/16![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 8/19. 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.
Tue 12/812:38 pm -
2 stops12h 49m
Sat 12/126:00 am -
2 stops8h 44m
Deal found 8/19![Delta logo]()
$513
This United Airlines deal was found by Cheapflights users on 8/18. 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 12/88:30 am -
1 stop14h 40m
Sat 12/1212:45 pm -
2 stops20h 54m
Deal found 8/18![United Airlines logo]()
$674
This Delta deal was found by Cheapflights users on 8/20. 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 12/1212:38 pm -
2 stops12h 49m
Tue 12/155:27 pm -
2 stops16h 27m
Deal found 8/20![Delta logo]()
$553
This United Airlines deal was found by Cheapflights users on 8/20. 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 12/128:30 am -
2 stops16h 39m
Tue 12/155:10 am -
1 stop13h 38m
Deal found 8/20![United Airlines logo]()
$694
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/158:45 am -
1 stop6h 16m
Wed 9/235:00 am -
1 stop13h 57m
Deal found 8/20![United Airlines logo]()
$721
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/158:45 am -
1 stop14h 23m
Tue 9/225:00 am -
1 stop13h 57m
Deal found 8/20![United Airlines logo]()
$721
Last-minute flights from Winnipeg to OregonDiscover last-minute flight deals from Winnipeg to Oregon. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Oregon. Data last updated August 21, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/17. 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 8/285:42 pm -
1 stop7h 38m
Sun 8/3012:35 am -
1 stop9h 19m
Deal found 8/17![Delta logo]()
$288
This United Airlines deal was found by Cheapflights users on 8/17. 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 8/288:45 am -
1 stop8h 20m
Mon 8/315:30 am -
2 stops28h 22m
Deal found 8/17![United Airlines logo]()
$519
This Delta deal was found by Cheapflights users on 8/20. 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 9/912:41 pm -
1 stop9h 35m
Fri 9/1112:25 am -
1 stop9h 26m
Deal found 8/20![Delta logo]()
$289
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/98:45 am -
2 stops14h 02m
Sat 9/127:02 am -
1 stop13h 31m
Deal found 8/20![United Airlines logo]()
$387
This Delta deal was found by Cheapflights users on 8/20. 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.
Tue 9/153:58 pm -
2 stops9h 19m
Tue 9/225:29 pm -
2 stops16h 22m
Deal found 8/20![Delta logo]()
$526
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/1512:50 pm -
3 stops13h 09m
Tue 9/2210:29 am -
2 stops28h 56m
Deal found 8/20![Multiple Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/158:45 am -
1 stop14h 23m
Tue 9/225:00 am -
1 stop13h 57m
Deal found 8/20![United Airlines logo]()
$721
This Air Canada deal was found by Cheapflights users on 8/18. 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 9/185:45 am -
1 stop5h 46m
Sun 9/207:45 pm -
1 stop5h 12m
Deal found 8/18![Air Canada logo]()
$361
This United deal was found by Cheapflights users on 8/18. 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.
Fri 9/187:00 am -
2 stops19h 37m
Sun 9/207:45 pm -
1 stop5h 12m
Deal found 8/18![Multiple Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 8/17. 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 9/3012:41 pm -
1 stop9h 35m
Sat 10/103:00 pm -
1 stop6h 19m
Deal found 8/17![Delta logo]()
$300
This United Airlines deal was found by Cheapflights users on 8/20. 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 9/308:45 am -
1 stop14h 25m
Sat 10/104:07 pm -
2 stops18h 30m
Deal found 8/20![United Airlines logo]()
$367
This Air Canada deal was found by Cheapflights users on 8/20. 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 9/307:20 am -
2 stops13h 51m
Sat 10/107:45 pm -
2 stops14h 34m
Deal found 8/20![Air Canada logo]()
$422
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 August 21, 2026.
Search for one-way flight options from Winnipeg to Oregon. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This deal was found by Cheapflights users on 8/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/610:10 am -
1 stop5h 40m
Deal found 8/17![WestJet logo]()
$122
This deal was found by Cheapflights users on 8/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/110:10 am -
1 stop5h 40m
Deal found 8/17![WestJet logo]()
$123
This Delta deal was found by Cheapflights users on 8/17. 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 9/173:58 pm -
1 stop9h 12m
Deal found 8/17![Delta logo]()
$171
This Delta deal was found by Cheapflights users on 8/20. 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 9/1912:41 pm -
1 stop9h 35m
Deal found 8/20![Delta logo]()
$172
This Air Canada deal was found by Cheapflights users on 8/17. 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 10/2810:55 am -
1 stop5h 46m
Deal found 8/17![Air Canada logo]()
$180
This Air Canada deal was found by Cheapflights users on 8/17. 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.
Tue 9/155:45 am -
1 stop5h 46m
Deal found 8/17![Air Canada logo]()
$199
This deal was found by Cheapflights users on 8/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am -
1 stop5h 31m
Deal found 8/17![Air Canada logo]()
$203
This Air Canada deal was found by Cheapflights users on 8/18. 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 9/245:45 am -
1 stop5h 46m
Deal found 8/18![Air Canada logo]()
$205
This Air Canada deal was found by Cheapflights users on 8/18. 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 9/237:20 am -
2 stops9h 26m
Deal found 8/18![Air Canada logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/184:55 pm -
2 stops18h 12m
Deal found 8/19![Multiple Airlines logo]()
$208
This Air Canada deal was found by Cheapflights users on 8/21. 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 9/105:45 am -
1 stop5h 46m
Deal found 8/21![Air Canada logo]()
$209
This Trip.com deal was found by Cheapflights users on 8/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:10 am -
2 stops11h 57m
Deal found 8/20![Multiple Airlines logo]()
$227
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 August 21, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $289 (Delta) |
One-way from | $122 |
Popular in | April |
Cheapest in | June |
Average price | $346 |
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 August 21, 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
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 8/28
5:42 pm-11:20 pm
1 stop7h 38m
Portland
Sun 8/30
12:35 am-11:54 am
1 stop9h 19m
$288
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/2
5:42 pm-11:20 pm
1 stop7h 38m
Portland
Tue 9/8
12:25 am-11:51 am
1 stop9h 26m
$288
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/9
12:41 pm-8:16 pm
1 stop9h 35m
Portland
Fri 9/11
12:25 am-11:51 am
1 stop9h 26m
$289
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/30
12:41 pm-8:16 pm
1 stop9h 35m
Portland
Sat 10/10
3:00 pm-11:19 pm
1 stop6h 19m
$300
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Tue 10/27
10:55 am-2:41 pm
1 stop5h 46m
Portland
Sat 10/31
10:00 am-12:09 am
2 stops12h 09m
$360
Quickest round-trip
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 9/18
5:45 am-9:31 am
1 stop5h 46m
Portland
Sun 9/20
7:45 pm-2:57 am
1 stop5h 12m
$361
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Fri 9/18
7:00 am-12:37 am
2 stops19h 37m
Portland
Sun 9/20
7:45 pm-2:57 am
1 stop5h 12m
$366
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Wed 9/30
8:45 am-10:53 pm
1 stop16h 08m
Portland
Sat 10/10
4:07 pm-12:37 pm
2 stops18h 30m
$366
WinnipegPortland
YWG Winnipeg - PDX Portland
YWGPDX
Winnipeg
Mon 8/31
8:45 am-8:59 pm
2 stops14h 14m
Portland
Wed 9/9
11:02 pm-11:52 am
1 stop10h 50m
$369
WinnipegMedford
YWG Winnipeg - MFR Medford
YWGMFR
Winnipeg
Tue 12/8
12:38 pm-11:27 pm
2 stops12h 49m
Medford
Sat 12/12
6:00 am-4:44 pm
2 stops8h 44m
$513
Showing 1-10 of 29 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
YWG-MFR
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
YWG-MFR
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 April is currently the most expensive (average of $542). 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 $290 and $408 in September.The cheapest round-trip price found within the last 5 days was $289 on Delta (Sep 9-Sep 11).
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 August 21, 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.
Overall
7.1
Entertainment
6.8
Comfort
7.1
Crew
7.8
Boarding
7.3
Food
6.3
Reviews
1 / 20
8.0
ExcellentMicheline,Aug 2026
YUL - LAX
Overall
7.1
Entertainment
6.8
Comfort
7.1
Crew
7.8
Boarding
7.3
Food
6.3
Reviews
1 / 20
8.0
ExcellentMicheline,Aug 2026
YUL - LAX
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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Oregon by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Winnipeg to Oregon by cabin class
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 August 21, 2026.
Popular flight searches
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Winnipeg to Oregon flights
Consider these flights traveling from Winnipeg to Oregon.
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 August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$299 | Average$437 | FlexibilityNo cancel fee | On-time67% |