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Cheap flights from Winnipeg to Portland from C$ 186

YWG — PDX
9 Oct — 16 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Winnipeg to Portland

Enter your travel dates to find the best prices.

Cheapest flights from Winnipeg to Portland

Wed 21/105:45 a.m. -
1 stop5h 46m
Wed 28/103:20 p.m. -
1 stop7h 12m
Deal found 5/9C$ 356
Fri 6/115:40 a.m. -
1 stop5h 46m
Mon 9/113:15 p.m. -
2 stops6h 54m
Deal found 7/9C$ 361
Sun 20/95:45 a.m. -
1 stop5h 46m
Sun 27/97:45 p.m. -
1 stop5h 12m
Deal found 9/9C$ 389
Wed 21/105:40 p.m. -
1 stop8h 04m
Wed 28/108:44 p.m. -
2 stops13h 04m
Deal found 5/9C$ 510
Sun 20/94:15 p.m. -
2 stops23h 35m
Sun 27/92:30 p.m. -
1 stop24h 55m
Deal found 9/9C$ 554
Fri 6/112:15 p.m. -
2 stops21h 21m
Mon 9/117:26 p.m. -
2 stops14h 57m
Deal found 7/9C$ 659
Sun 20/95:25 p.m. -
3 stops22h 25m
Sun 27/92:30 p.m. -
2 stops16h 50m
Deal found 9/9C$ 691
Wed 21/107:00 a.m. -
2 stops17h 53m
Wed 28/101:15 p.m. -
2 stops21h 08m
Deal found 5/9C$ 705
Wed 9/97:20 a.m. -
2 stops9h 26m
Sat 12/93:43 p.m. -
2 stops9h 14m
Deal found 4/9C$ 882

Find flight deals from Winnipeg to Portland

Round-trip from

C$ 356

One-way from

C$ 186

Popular in

April

Cheapest in

June

Average price

C$ 602
Air Canada
  • Air Canada
  • 21/10-28/10
  • 2 total stops
  • 12h 58m total
  • Winnipeg to Portland
Search Deals
WestJet
  • WestJet
  • 23/9-31/12
  • 1 total stop
  • 5h 40m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 102 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2026
Search Deals

Cheapflights Fare Finder

 
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

Price

Cheapest round-trip

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Sat 24/10

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 205

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Fri 25/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 218

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Sat 24/10

6:00 a.m.-4:44 p.m.

2 stops12h 44m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 305

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Wed 16/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 306

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Wed 21/10

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Wed 28/10

3:20 p.m.-12:32 a.m.

1 stop7h 12m

C$ 356

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Mon 15/2

12:30 p.m.-8:23 p.m.

1 stop9h 53m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 358

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Fri 6/11

5:40 a.m.-9:26 a.m.

1 stop5h 46m

Portland

Mon 9/11

3:15 p.m.-12:09 a.m.

2 stops6h 54m

C$ 361

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Sun 20/9

5:45 a.m.-9:31 a.m.

1 stop5h 46m

Portland

Sun 27/9

7:45 p.m.-2:57 a.m.

1 stop5h 12m

C$ 389

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Tue 16/2

7:00 a.m.-7:17 p.m.

1 stop14h 17m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 398
Quickest round-trip

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Mon 21/9

10:10 a.m.-1:50 p.m.

1 stop5h 40m

Portland

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 400

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 21 resultsSorted by cheapest first
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3

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.
Estimated round-trip price

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, June is the cheapest month in which you can book a flight from Winnipeg to Portland (average of C$ 455). Flying from Winnipeg to Portland in April is currently the most expensive (average of C$ 747). 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?

Airfare is below average for this route at the moment.

Winnipeg to Portland flights typically cost between C$ 379 and C$ 647 in October.
The cheapest round-trip price found within the last 5 days was C$ 356 on Air Canada (21 Oct-28 Oct).

Reviews of airlines servicing Portland

Get a feel of what it's like to fly with WestJet and Air Canada from Winnipeg to Portland by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
WestJet
7.2
Good
3,446 reviews
Check prices

Food

6.2

Comfort

7.1

Overall

7.2

Entertainment

6.1

Crew

7.9

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
WestJet
7.2
Good
3,446 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Food

6.2

Comfort

7.1

Overall

7.2

Entertainment

6.1

Crew

7.9

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment
Air Canada
7.1
Good
11,608 reviews
WestJet
7.2
Good
3,446 reviews
Check prices

Food

6.2

Comfort

7.1

Overall

7.2

Entertainment

6.1

Crew

7.9

Boarding

7.4

Reviews

1 / 20
10.0
Excellent

Anonymous,Aug 2026

YHZ - DTW

Better snacks I also flew Delta much better with movies and entertainment

Related info for your journey

  • How long is the flight from Winnipeg to Portland?

    There are many flights that can get you from Winnipeg to Portland in 5h 46m. Fly via Air Canada, Delta, or WestJet to get the fastest option. The distance between Winnipeg and Portland is about 1944 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • What are the cheapest airlines flying from Winnipeg to Portland round-trip?

    According to our current data, WestJet (C$ 302), and Air Canada (C$ 344) offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 49% less than the average price by searching for these airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Portland 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 Winnipeg to Portland?

    Currently, June is the cheapest month in which you can book a flight from Winnipeg to Portland (average of C$ 455). Flying from Winnipeg to Portland in April is currently the most expensive (average of C$ 747). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Vancouver
Salem
Cannon Beach
Lincoln City
Gresham

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to Portland

Winnipeg to Medford flights

Top 2 airlines flying from Winnipeg to Portland

AirlineCheapestAverageFlexibilityOn-time
WestJetCheapestC$ 302AverageC$ 441FlexibilityNo cancel feeOn-time60%
Search WestJet flights
Air CanadaCheapestC$ 344AverageC$ 591FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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

Deals for Winnipeg to Portland flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Winnipeg to Portland for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Winnipeg to Portland with no change fees?

Certainly. Search results for flights to Portland from Winnipeg shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

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Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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