$230+ Cheap flights from Oregon to Winnipeg (YWG)
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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
Nov 5 — Nov 121
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Oregon to Winnipeg 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 Oregon to Winnipeg
Cheapest
Best
Last-minute
One-way
Cheapest flights from Oregon to WinnipegExplore the most affordable flight options available from Oregon to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2026.
Explore the most affordable flight options available from Oregon to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 6, 2026.
This Air Canada deal was found by Cheapflights users on 10/3. 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 10/197:45 pm -
1 stop5h 12m
Sat 10/245:45 am -
1 stop5h 46m
Deal found 10/3![Air Canada logo]()
$508
This United Airlines 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:02 am -
1 stop13h 31m
Wed 10/212:00 pm -
1 stop10h 23m
Deal found 10/5![United Airlines logo]()
$546
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:21 am -
2 stops9h 13m
Sun 12/135:24 pm -
2 stops7h 37m
Deal found 10/6![Delta logo]()
$611
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.
Tue 10/203:30 pm -
1 stop6h 55m
Wed 10/215:45 am -
1 stop5h 46m
Deal found 10/4![Air Canada logo]()
$617
This United deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:20 am -
2 stops9h 26m
Deal found 10/3![Multiple Airlines logo]()
$623
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:00 am -
3 stops13h 31m
Deal found 10/3![United Airlines logo]()
$642
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/253:15 pm -
1 stop8h 17m
Sat 1/211:05 pm -
1 stop12h 21m
Deal found 10/5![Air Canada logo]()
$709
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:04 am -
2 stops12h 46m
Sun 12/137:00 am -
3 stops11h 51m
Deal found 10/6![Multiple Airlines logo]()
$919
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:00 am -
1 stop13h 55m
Sun 12/138:40 am -
1 stop6h 15m
Deal found 10/6![United Airlines logo]()
$954
Best flights from Oregon to WinnipegDiscover carefully curated flight deals from Oregon to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 6, 2026.
Discover carefully curated flight deals from Oregon to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 6, 2026.
This United Airlines 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:02 am -
1 stop13h 31m
Wed 10/212:00 pm -
1 stop10h 23m
Deal found 10/5![United Airlines logo]()
$546
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:21 am -
2 stops9h 13m
Sun 12/135:24 pm -
2 stops7h 37m
Deal found 10/6![Delta logo]()
$611
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.
Tue 10/203:30 pm -
1 stop6h 55m
Wed 10/215:45 am -
1 stop5h 46m
Deal found 10/4![Air Canada logo]()
$617
This United deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:20 am -
2 stops9h 26m
Deal found 10/3![Multiple Airlines logo]()
$623
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:00 am -
3 stops13h 31m
Deal found 10/3![United Airlines logo]()
$642
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/46:04 am -
2 stops12h 46m
Sun 12/137:00 am -
3 stops11h 51m
Deal found 10/6![Multiple Airlines logo]()
$919
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/45:00 am -
1 stop13h 55m
Sun 12/138:40 am -
1 stop6h 15m
Deal found 10/6![United Airlines logo]()
$954
Last-minute flights from Oregon to WinnipegDiscover last-minute flight deals from Oregon to Winnipeg. Data last updated October 6, 2026 and is based on user searches.
Discover last-minute flight deals from Oregon to Winnipeg. Data last updated October 6, 2026 and is based on user searches.
This Air Canada deal was found by Cheapflights users on 10/3. 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 10/197:45 pm -
1 stop5h 12m
Sat 10/245:45 am -
1 stop5h 46m
Deal found 10/3![Air Canada logo]()
$508
This United deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:20 am -
2 stops9h 26m
Deal found 10/3![Multiple Airlines logo]()
$623
This United Airlines deal was found by Cheapflights users on 10/3. 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 10/1911:30 pm -
1 stop11h 07m
Sat 10/247:00 am -
3 stops13h 31m
Deal found 10/3![United Airlines logo]()
$642
This United Airlines 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 Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:02 am -
1 stop13h 31m
Wed 10/212:00 pm -
1 stop10h 23m
Deal found 10/5![United Airlines logo]()
$546
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.
Tue 10/203:30 pm -
1 stop6h 55m
Wed 10/215:45 am -
1 stop5h 46m
Deal found 10/4![Air Canada logo]()
$617
One-way flights from Oregon to WinnipegSearch for one-way flight options from Oregon to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 6, 2026.
Search for one-way flight options from Oregon to Winnipeg. Find affordable one-way fares based on user searches. Data last updated October 6, 2026.
This Delta deal was found by Cheapflights users on 10/1. 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 11/311:51 am -
1 stop10h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$230
This Delta deal was found by Cheapflights users on 10/1. 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 10/2511:51 am -
1 stop9h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Delta logo]()
$239
This Air Canada deal was found by Cheapflights users on 10/1. 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 10/283:20 pm -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Thu 11/510:59 am -
2 stops35h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$255
This Air Canada deal was found by Cheapflights users on 10/1. 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 11/43:15 pm -
2 stops7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Thu 10/299:33 pm -
2 stops26h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 11/211:06 am -
3 stops35h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/275:45 pm -
2 stops29h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 10/1. 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.
Sat 10/3110:28 am -
1 stop13h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$272
This Air Canada deal was found by Cheapflights users on 10/1. 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 10/293:20 pm -
1 stop7h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Air Canada logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 10/1. 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 10/2810:48 am -
3 stops49h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$282
Find flight deals from Oregon to Winnipeg
Keep the following information in mind while searching for Oregon to Winnipeg flight deals. Data was last updated October 6, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $508 (Air Canada) |
One-way from | $230 (Delta) |
Popular in | February |
Cheapest in | November |
Average price | $521 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oregon to Winnipeg 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 6, 2026.
Use the filters below to find and compare flights from Oregon to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Tue 11/3
11:51 am-1:19 am
1 stop10h 28m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$230
Quickest round-trip
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Wed 11/4
3:22 pm-1:19 am
1 stop6h 57m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$230
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 10/26
11:51 am-11:19 pm
1 stop9h 28m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$239
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sun 10/25
11:51 am-11:19 pm
1 stop9h 28m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$239
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Thu 10/29
9:33 pm-1:44 am
2 stops26h 11m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$266
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Sat 11/7
3:15 pm-2:32 am
1 stop8h 17m
Winnipeg
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$300
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Tue 10/20
7:02 am-10:33 pm
1 stop13h 31m
Winnipeg
Wed 10/21
2:00 pm-10:23 pm
1 stop10h 23m
$546
RedmondWinnipeg
RDM Bend/Redmond - YWG Winnipeg
RDMYWG
Bend/Redmond
Fri 12/4
6:21 am-6:34 pm
2 stops9h 13m
Winnipeg
Sun 12/13
5:24 pm-10:01 pm
2 stops7h 37m
$611
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Tue 10/20
3:30 pm-12:25 am
1 stop6h 55m
Winnipeg
Wed 10/21
5:45 am-9:31 am
1 stop5h 46m
$617
PortlandWinnipeg
PDX Portland - YWG Winnipeg
PDXYWG
Portland
Mon 10/19
11:30 pm-12:37 pm
1 stop11h 07m
Winnipeg
Sat 10/24
7:20 am-2:46 pm
2 stops9h 26m
$623
Showing 1-10 of 13 resultsSorted by cheapest first
Best time to book a flight from Oregon to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oregon with our price prediction graph.
PDX-YWG
RDM-YWG
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 Oregon to Winnipeg
USOR-YWG
PDX-YWG
RDM-YWG
What is the cheapest month to book a flight from Oregon to Winnipeg?
Currently, November is the cheapest month in which you can book a flight from Oregon to Winnipeg (average of $364). Flying from Oregon to Winnipeg in February is currently the most expensive (average of $878). 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 Oregon to Winnipeg?
Airfare is typical for this route at the moment.
Oregon to Winnipeg flights typically cost between $456 and $608 in October.The cheapest round-trip price found within the last 5 days was $508 on Air Canada (Oct 19-Oct 24).
Related info for your journey
Find useful and relevant information for your journey from Oregon to Winnipeg. 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 Winnipeg?
Book flights to Winnipeg if you plan to visit one of these locationsPortage la Prairie
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.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Winnipeg flight routes
Alternative routes for Oregon to Winnipeg
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Winnipeg by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oregon to Winnipeg by cabin class
Find flights from Oregon to Winnipeg, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oregon and Winnipeg flights
Browse other Oregon and Winnipeg flight options. Last updated on October 6, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Winnipeg
Explore flights to Winnipeg departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 6, 2026.
Top 3 airlines flying from Oregon to Winnipeg
Discover the top 3 airlines that operate flights from Oregon to Winnipeg. 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 6, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$163 | Average$419 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$497 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$245 | Average$431 | FlexibilityNo cancel fee | On-time60% |