$131+ Cheap flights from Portland (PDX) to Winnipeg (YWG)
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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
PDX — YWG
May 27 — Jun 31
Round-trip
1 adult, Economy
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Find cheap flights from Portland 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
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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 Portland to Winnipeg
Cheapest
Best
Last-minute
One-way
Cheapest flights from Portland to WinnipegExplore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
Explore the most affordable flight options available from Portland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
This Trip.com deal was found by Cheapflights users on 4/27. 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.
Mon 7/62:30 pm
PDX
- YWG
1 stop7h 10m
WestJet
Sat 7/117:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 4/27![WestJet logo]()
$235
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Wed 8/122:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Thu 8/2010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/26![WestJet logo]()
$263
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Wed 9/232:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Wed 9/3010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/26![WestJet logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Mon 6/2910:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$281
This Trip.com deal was found by Cheapflights users on 4/24. 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.
Wed 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Tue 5/2610:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/24![WestJet logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 4/25. 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 6/92:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Tue 6/1610:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/25![WestJet logo]()
$288
This FlightHub deal was found by Cheapflights users on 4/25. 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.
Thu 8/132:30 pm
PDX
- YWG
2 stops19h 30m
WestJet
Mon 8/1710:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/25![WestJet logo]()
$292
Best flights from Portland to WinnipegDiscover carefully curated flight deals from Portland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
Discover carefully curated flight deals from Portland to Winnipeg that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
This Delta deal was found by Cheapflights users on 4/26. 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 9/2511:39 am
PDX
- YWG
1 stop9h 48m
Delta
Sat 10/36:40 am
YWG
- PDX
1 stop8h 14m
Delta
Deal found 4/26![Delta logo]()
$319
This Booking.com deal was found by Cheapflights users on 4/25. 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.
Tue 6/92:30 pm
PDX
- YWG
2 stops16h 50m
WestJet
Tue 6/167:00 am
YWG
- PDX
2 stops8h 50m
WestJet
Deal found 4/25![WestJet logo]()
$353
This Air Canada deal was found by Cheapflights users on 4/24. 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 8/157:45 pm
PDX
- YWG
1 stop15h 25m
Air Canada
Wed 8/195:40 am
YWG
- PDX
1 stop5h 51m
Air Canada
Deal found 4/24![Air Canada logo]()
$367
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/274:15 pm
PDX
- YWG
2 stops17h 37m
United Airlines
Tue 6/237:00 am
YWG
- PDX
1 stop18h 53m
United Airlines
Deal found 4/22![United Airlines logo]()
$391
This Delta deal was found by Cheapflights users on 4/26. 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 9/2711:39 am
PDX
- YWG
1 stop9h 48m
Delta
Sun 10/412:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Deal found 4/26![Delta logo]()
$319
This Delta deal was found by Cheapflights users on 4/26. 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 9/2611:39 am
PDX
- YWG
1 stop9h 48m
Delta
Sat 10/38:50 am
YWG
- PDX
1 stop9h 08m
Delta
Deal found 4/26![Delta logo]()
$319
This Trip.com deal was found by Cheapflights users on 4/27. 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.
Thu 6/112:30 pm
PDX
- YWG
1 stop18h 40m
WestJet
Thu 6/1810:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/27![WestJet logo]()
$450
This Delta deal was found by Cheapflights users on 4/26. 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 9/207:40 pm
PDX
- YWG
2 stops13h 54m
Delta
Mon 9/2812:40 pm
YWG
- PDX
1 stop9h 35m
Delta
Deal found 4/26![Delta logo]()
$446
This Delta deal was found by Cheapflights users on 4/27. 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 6/1111:46 am
PDX
- YWG
1 stop9h 43m
Delta
Thu 6/183:54 pm
YWG
- PDX
1 stop9h 24m
Delta
Deal found 4/27![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/23. 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 5/176:15 am
PDX
- YWG
1 stop6h 40m
Delta
Fri 6/263:54 pm
YWG
- PDX
1 stop9h 27m
Delta
Deal found 4/23![Delta logo]()
$493
This Delta deal was found by Cheapflights users on 4/24. 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 5/1211:58 am
PDX
- YWG
1 stop9h 28m
Delta
Fri 5/1511:55 am
YWG
- PDX
1 stop10h 16m
Delta
Deal found 4/24![Delta logo]()
$498
This Delta deal was found by Cheapflights users on 4/23. 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 5/176:15 am
PDX
- YWG
1 stop6h 40m
Delta
Wed 6/243:54 pm
YWG
- PDX
1 stop9h 27m
Delta
Deal found 4/23![Delta logo]()
$512
Last-minute flights from Portland to WinnipegDiscover last-minute flight deals from Portland to Winnipeg. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Winnipeg. Data last updated April 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Mon 6/2910:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$281
This Trip.com deal was found by Cheapflights users on 4/24. 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.
Wed 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Tue 5/2610:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/24![WestJet logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Mon 5/2510:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/24![WestJet logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Wed 6/2410:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$299
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Sat 5/3010:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Sun 6/289:05 pm
YWG
- PDX
1 stop18h 45m
WestJet
Deal found 4/23![WestJet logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/222:30 pm
PDX
- YWG
2 stops16h 50m
WestJet
Mon 6/2910:10 am
YWG
- PDX
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$304
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/265:46 pm
PDX
- YWG
2 stops24h 29m
Multiple Airlines
Mon 6/110:10 am
YWG
- PDX
1 stop5h 40m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 4/23. 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 5/265:46 pm
PDX
- YWG
2 stops24h 29m
Multiple Airlines
Sat 5/3010:10 am
YWG
- PDX
1 stop5h 40m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$311
One-way flights from Portland to WinnipegSearch for one-way flight options from Portland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
Search for one-way flight options from Portland to Winnipeg. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Trip.com deal was found by Cheapflights users on 4/23. 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.
Wed 5/202:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/222:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 4/27![WestJet logo]()
$140
This deal was found by Cheapflights users on 4/23. 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 5/263:30 pm
PDX
- YWG
1 stop6h 19m
Air Canada
Deal found 4/23![Air Canada logo]()
$149
This Delta deal was found by Cheapflights users on 4/24. 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 5/1211:58 am
PDX
- YWG
1 stop9h 28m
Delta
Deal found 4/24![Delta logo]()
$154
This United Airlines deal was found by Cheapflights users on 4/26. 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 6/14:15 pm
PDX
- YWG
2 stops17h 37m
United Airlines
Deal found 4/26![United Airlines logo]()
$155
This United Airlines deal was found by Cheapflights users on 4/27. 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 5/117:45 pm
PDX
- YWG
2 stops14h 07m
United Airlines
Deal found 4/27![United Airlines logo]()
$159
This deal was found by Cheapflights users on 4/23. 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.
Sat 5/302:30 pm
PDX
- YWG
1 stop5h 40m
WestJet
Deal found 4/23![WestJet logo]()
$161
This Justfly.com deal was found by Cheapflights users on 4/27. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/132:30 pm
PDX
- YWG
2 stops22h 10m
WestJet
Deal found 4/27![WestJet logo]()
$163
This United Airlines deal was found by Cheapflights users on 4/24. 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 5/127:45 pm
PDX
- YWG
2 stops14h 07m
United Airlines
Deal found 4/24![United Airlines logo]()
$164
Find flight deals from Portland to Winnipeg
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PDX) to Winnipeg (YWG). 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 April 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $235 (Trip.com) |
One-way from | $131 (Trip.com) |
Popular in | February |
Cheapest in | November |
Average price | $638 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland 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 2,558,603 searches. Data last updated April 27, 2026.
Use the filters below to find and compare flights from Portland to Winnipeg that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Fri 9/25
11:39 am-11:27 pm
1 stop9h 48m
Winnipeg
Sat 10/3
6:40 am-12:54 pm
1 stop8h 14m
$319
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sun 9/27
11:39 am-11:27 pm
1 stop9h 48m
Winnipeg
Sun 10/4
12:40 pm-8:15 pm
1 stop9h 35m
$319
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sat 9/26
11:39 am-11:27 pm
1 stop9h 48m
Winnipeg
Sat 10/3
8:50 am-3:58 pm
1 stop9h 08m
$319
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Tue 6/9
2:30 pm-9:20 am
2 stops16h 50m
Winnipeg
Tue 6/16
7:00 am-1:50 pm
2 stops8h 50m
$353
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sat 8/15
7:45 pm-1:10 pm
1 stop15h 25m
Winnipeg
Wed 8/19
5:40 am-9:31 am
1 stop5h 51m
$367
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Wed 5/27
4:15 pm-11:52 am
2 stops17h 37m
Winnipeg
Tue 6/23
7:00 am-11:53 pm
1 stop18h 53m
$391
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sun 9/20
7:40 pm-11:34 am
2 stops13h 54m
Winnipeg
Mon 9/28
12:40 pm-8:15 pm
1 stop9h 35m
$446
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Thu 6/11
2:30 pm-11:10 am
1 stop18h 40m
Winnipeg
Thu 6/18
10:10 am-1:50 pm
1 stop5h 40m
$450
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Thu 6/11
11:46 am-11:29 pm
1 stop9h 43m
Winnipeg
Thu 6/18
3:54 pm-11:18 pm
1 stop9h 24m
$493
Quickest round-trip
PortlandWinnipeg
PDX - YWG
PDXYWG
Portland
Sun 5/17
6:15 am-2:55 pm
1 stop6h 40m
Winnipeg
Fri 6/26
3:54 pm-11:21 pm
1 stop9h 27m
$493
Showing 1-10 of 21 resultsSorted by cheapest first
Compare providers for flights from Portland to Winnipeg
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 Portland to Winnipeg in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland-Winnipeg flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland-Winnipeg 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 Portland-Winnipeg 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 Portland to Winnipeg
Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Portland with our price prediction graph.
PDX-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 Portland to Winnipeg
What is the cheapest month to book a flight from Portland to Winnipeg?
Currently, November is the cheapest month in which you can book a flight from Portland to Winnipeg (average of $247). Flying from Portland 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 Portland to Winnipeg?
Reviews of airlines servicing Winnipeg
Get insights into the airlines that provide service to Winnipeg. 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 Winnipeg. Reviews last updated April 27, 2026.
Read reviews from past customers who have flown Delta,WestJet, andAir Canada from Portland to Winnipeg. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Crew
8.5
Boarding
8.1
Comfort
7.9
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Portland to Winnipeg. 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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Portland and Winnipeg flights
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Top 3 airlines flying from Portland to Winnipeg
Discover the top 3 airlines that operate flights from Portland 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 2,558,603 searches. Data last updated April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$88 | Average$245 | FlexibilityNo cancel fee | On-time60% | |
| Cheapest$188 | Average$424 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$203 | Average$364 | FlexibilityNo cancel fee | On-time67% |