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Cheap flights from Portland to Winnipeg from C$ 369

PDX — YWG
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Portland to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Portland to Winnipeg

Wed 23/127:25 p.m. -
1 stop25h 20m
Thu 31/124:00 p.m. -
1 stop7h 35m
Deal found 23/10C$ 833
Wed 23/127:25 p.m. -
1 stop25h 20m
Wed 6/16:00 a.m. -
2 stops30h 32m
Deal found 24/10C$ 845
Thu 17/123:15 p.m. -
1 stop7h 17m
Wed 6/16:40 a.m. -
1 stop5h 46m
Deal found 25/10C$ 880
Fri 4/1210:00 a.m. -
2 stops12h 24m
Sat 5/126:40 a.m. -
1 stop5h 46m
Deal found 26/10C$ 889
Sun 6/126:08 p.m. -
2 stops48h 37m
Sun 13/126:30 a.m. -
1 stop11h 37m
Deal found 22/10C$ 894
Thu 24/127:00 a.m. -
1 stop13h 45m
Thu 31/124:00 p.m. -
1 stop7h 35m
Deal found 23/10C$ 900
Thu 24/126:25 a.m. -
2 stops15h 19m
Tue 29/1212:15 p.m. -
1 stop11h 24m
Deal found 23/10C$ 905
Thu 24/123:15 p.m. -
1 stop7h 17m
Sun 3/110:15 p.m. -
1 stop14h 11m
Deal found 26/10C$ 907
Thu 24/1211:52 p.m. -
1 stop11h 00m
Sun 3/13:15 p.m. -
2 stops21h 24m
Deal found 26/10C$ 915
Wed 23/127:25 p.m. -
1 stop25h 20m
Mon 28/124:00 p.m. -
1 stop20h 46m
Deal found 23/10C$ 918
Wed 23/127:25 p.m. -
1 stop25h 20m
Thu 7/111:00 a.m. -
2 stops36h 49m
Deal found 24/10C$ 919

Find flight deals from Portland to Winnipeg

Round-trip from

C$ 723

One-way from

C$ 369

Popular in

February

Cheapest in

November

Average price

C$ 667
31/1-4/2
  • 31/1-4/2
  • 3 total stops
  • 29h 39m total
  • Portland to Winnipeg
Search Deals
23/12-31/12
  • 23/12-31/12
  • 1 total stop
  • 25h 20m total
  • Portland to Winnipeg
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

Cheapflights Fare Finder

 
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

Price

Cheapest round-trip

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Fri 18/12

11:50 p.m.-1:52 p.m.

1 stop11h 02m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 444

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Mon 21/12

11:59 a.m.-12:44 a.m.

1 stop9h 45m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 444

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Thu 17/12

4:28 p.m.-1:52 p.m.

2 stops18h 24m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 451

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Wed 23/12

7:41 p.m.-12:25 p.m.

2 stops13h 44m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 463

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Fri 6/11

3:40 p.m.-1:23 p.m.

2 stops18h 43m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 482

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Sat 7/11

1:25 p.m.-1:23 p.m.

2 stops20h 58m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 482

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Fri 6/11

6:08 a.m.-10:15 a.m.

2 stops25h 07m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 603
Quickest round-trip

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Thu 5/11

3:22 p.m.-12:19 a.m.

1 stop5h 57m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 607

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Sun 1/11

7:26 p.m.-1:23 p.m.

2 stops14h 57m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 607

PortlandWinnipeg

PDX Portland - YWG Winnipeg

PDXYWG

Portland

Thu 5/11

9:00 a.m.-9:57 p.m.

2 stops9h 57m

Winnipeg

Wed 31/12

12:00 a.m.-10:00 p.m.

Nonstop0h 00m

C$ 607

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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.
Estimated round-trip price

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 C$ 510). Flying from Portland to Winnipeg in February is currently the most expensive (average of C$ 1,231). 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?

Airfare is typical for this route at the moment.

Portland to Winnipeg flights typically cost between C$ 282 and C$ 926 in January.
The cheapest round-trip price found within the last 5 days was C$ 723 on Multiple Airlines (31 Jan-4 Feb).

Related info for your journey

  • How long is the flight from Portland to Winnipeg?

    A quick flight from Portland to Winnipeg can take about 7h 17m. Air Canada provides one of the quickest options available for as low as C$ 880. The distance from Portland to Winnipeg is about 1944 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • Can I find deals for flights from Portland to Winnipeg that include hotel bookings?

    Yes. In addition to deals on Portland to Winnipeg flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Winnipeg?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Winnipeg.

  • Can I find deals for business class flights from Portland to Winnipeg?

    Yes. Cheapflights offers flight deals from Portland to Winnipeg by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • 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 C$ 510). Flying from Portland to Winnipeg in February is currently the most expensive (average of C$ 1,231). 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.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Selkirk

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Thompson car rentals

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How does Cheapflights help users find flights from Portland to Winnipeg?

Cheapflights makes it easy to find Portland to Winnipeg flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Portland to Winnipeg?

Millions of users choose and trust Cheapflights to book the best flight deals from Portland to Winnipeg for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Portland to Winnipeg flexibly with Cheapflights today.

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