$166+ Cheap flights from Winnipeg (YWG) to Portland (PDX)
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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — PDX
Jun 4 — Jun 111
Round-trip
1 adult, Economy
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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
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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 May 5, 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 May 5, 2026.
This oojo deal was found by Cheapflights users on 5/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Wed 9/92:30 pm
PDX
- YWG
1 stop7h 10m
WestJet
Deal found 5/3![WestJet logo]()
$219
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/17:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/3010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Fri 6/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$273
This Delta deal was found by Cheapflights users on 4/30. 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 9/2212:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Fri 9/2512:40 am
PDX
- YWG
1 stop8h 54m
Delta
Deal found 4/30![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Fri 9/2512:40 am
PDX
- YWG
1 stop8h 54m
Delta
Deal found 5/3![Delta logo]()
$276
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Fri 6/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$281
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 May 5, 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 May 5, 2026.
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Fri 9/2512:40 am
PDX
- YWG
1 stop8h 54m
Delta
Deal found 5/3![Delta logo]()
$276
This Air Canada deal was found by Cheapflights users on 5/4. 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 9/2310:50 am
YWG
- PDX
1 stop6h 01m
Air Canada
Sat 9/2610:10 am
PDX
- YWG
1 stop5h 37m
Air Canada
Deal found 5/4![Air Canada logo]()
$286
This oojo deal was found by Cheapflights users on 5/4. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Wed 6/102:30 pm
PDX
- YWG
1 stop19h 45m
WestJet
Deal found 5/4![WestJet logo]()
$293
This Delta deal was found by Cheapflights users on 5/1. 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 9/2212:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Fri 9/2512:40 am
PDX
- YWG
1 stop8h 54m
Delta
Deal found 5/1![Delta logo]()
$277
This Delta deal was found by Cheapflights users on 5/5. 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.
Fri 7/103:59 pm
YWG
- PDX
1 stop9h 19m
Delta
Sat 7/1112:33 am
PDX
- YWG
1 stop9h 20m
Delta
Deal found 5/5![Delta logo]()
$330
This Delta deal was found by Cheapflights users on 5/1. 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.
Wed 6/311:55 am
YWG
- PDX
1 stop10h 16m
Delta
Sat 6/611:58 am
PDX
- YWG
1 stop9h 28m
Delta
Deal found 5/1![Delta logo]()
$337
This Delta deal was found by Cheapflights users on 5/1. 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 5/3111:55 am
YWG
- PDX
1 stop10h 16m
Delta
Wed 6/1011:46 am
PDX
- YWG
1 stop9h 43m
Delta
Deal found 5/1![Delta logo]()
$344
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/712:46 pm
YWG
- PDX
1 stop9h 31m
Delta
Sun 6/148:42 pm
PDX
- YWG
2 stops13h 14m
Delta
Deal found 5/3![Delta logo]()
$411
Last-minute flights from Winnipeg to PortlandDiscover last-minute flight deals from Winnipeg to Portland. Data last updated May 5, 2026 and is based on user searches.
Discover last-minute flight deals from Winnipeg to Portland. Data last updated May 5, 2026 and is based on user searches.
This oojo deal was found by Cheapflights users on 5/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/217:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Fri 5/292:30 pm
PDX
- YWG
1 stop19h 45m
WestJet
Deal found 5/3![WestJet logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 5/3010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$273
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/307:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Fri 6/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/17:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$264
This oojo deal was found by Cheapflights users on 5/1. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/27:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Tue 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$245
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/210:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Fri 6/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$281
This oojo deal was found by Cheapflights users on 5/4. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Wed 6/102:30 pm
PDX
- YWG
2 stops19h 30m
WestJet
Deal found 5/4![WestJet logo]()
$287
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Fri 6/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 5/1![WestJet logo]()
$286
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 May 5, 2026.
Search for one-way flight options from Winnipeg to Portland. Find affordable one-way fares based on user searches. Data last updated May 5, 2026.
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2912:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Deal found 5/3![Delta logo]()
$166
This WestJet deal was found by Cheapflights users on 5/1. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 5/1![WestJet logo]()
$172
This Air Canada deal was found by Cheapflights users on 5/2. 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 6/65:40 am
YWG
- PDX
1 stop5h 50m
Air Canada
Deal found 5/2![Air Canada logo]()
$173
This oojo deal was found by Cheapflights users on 5/3. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/177:00 am
YWG
- PDX
2 stops32h 50m
WestJet
Deal found 5/3![WestJet logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/179:05 pm
YWG
- PDX
3 stops24h 42m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$246
This Mytrip deal was found by Cheapflights users on 5/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/295:25 pm
YWG
- PDX
3 stops22h 25m
Multiple Airlines
Deal found 5/3![Multiple Airlines logo]()
$278
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 May 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $219 (oojo) |
One-way from | $166 (Delta) |
Popular in | March |
Cheapest in | August |
Average price | $409 |
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 2,558,603 searches. Data last updated May 5, 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
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Wed 9/23
12:40 pm-8:15 pm
1 stop9h 35m
Portland
Fri 9/25
12:40 am-11:34 am
1 stop8h 54m
$276
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Tue 9/22
12:40 pm-8:15 pm
1 stop9h 35m
Portland
Fri 9/25
12:40 am-11:34 am
1 stop8h 54m
$277
Quickest round-trip
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Wed 9/23
10:50 am-2:51 pm
1 stop6h 01m
Portland
Sat 9/26
10:10 am-5:47 pm
1 stop5h 37m
$286
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Wed 6/3
7:00 am-1:50 pm
2 stops8h 50m
Portland
Wed 6/10
2:30 pm-12:15 pm
1 stop19h 45m
$293
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Fri 7/10
3:59 pm-11:18 pm
1 stop9h 19m
Portland
Sat 7/11
12:33 am-11:53 am
1 stop9h 20m
$330
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Wed 6/3
11:55 am-8:11 pm
1 stop10h 16m
Portland
Sat 6/6
11:58 am-11:26 pm
1 stop9h 28m
$337
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Sun 5/31
11:55 am-8:11 pm
1 stop10h 16m
Portland
Wed 6/10
11:46 am-11:29 pm
1 stop9h 43m
$344
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Sun 6/7
12:46 pm-8:17 pm
1 stop9h 31m
Portland
Sun 6/14
8:42 pm-11:56 am
2 stops13h 14m
$411
Cheapest one-way
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Tue 9/29
12:40 pm-8:15 pm
1 stop9h 35m
$166
Quickest one-way
WinnipegPortland
YWG - PDX
YWGPDX
Winnipeg
Sat 6/6
5:40 am-9:30 am
1 stop5h 50m
$172
Showing 1-10 of 12 resultsSorted by cheapest first
Compare providers for flights from Winnipeg to Portland
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Winnipeg to Portland in May.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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
What is the cheapest month to book a flight from Winnipeg to Portland?
Currently, August is the cheapest month in which you can book a flight from Winnipeg to Portland (average of $224). Flying from Winnipeg to Portland in March is currently the most expensive (average of $572). 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 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 May 5, 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.
Comfort
7.1
Crew
7.8
Food
6.3
Boarding
7.3
Entertainment
6.8
Overall
7.1
Reviews
1 / 20
6.0
GoodPaula,Mar 2026
YVR - PSP
Comfort
7.1
Crew
7.8
Food
6.3
Boarding
7.3
Entertainment
6.8
Overall
7.1
Reviews
1 / 20
6.0
GoodPaula,Mar 2026
YVR - PSP
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
Vancouver
Lincoln City
Longview
Lake Oswego
Hillsboro
Clackamas
Troutdale
Cannon Beach
Long Beach
McMinnville
Tigard
The Dalles
Wilsonville
Depoe Bay
Stevenson
Tillamook
Astoria
Pacific City
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.
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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 May 5, 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 May 5, 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 May 5, 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 2,558,603 searches. Data last updated May 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$214 | Average$384 | FlexibilityNo cancel fee | On-time67% |