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Cheap flights from Winnipeg to Portland from C$ 315

YWG — PDX
24 Nov — 1 Dec1
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

Fri 20/116:40 a.m. -
1 stop5h 46m
Fri 27/113:15 p.m. -
2 stops7h 04m
Deal found 21/10C$ 723
Sat 5/126:40 a.m. -
1 stop5h 46m
Mon 14/123:15 p.m. -
1 stop7h 17m
Deal found 22/10C$ 725
Sun 20/1212:15 p.m. -
1 stop11h 24m
Thu 31/1211:05 a.m. -
2 stops22h 20m
Deal found 22/10C$ 732
Sun 22/115:45 p.m. -
1 stop9h 01m
Sat 28/1112:35 a.m. -
1 stop8h 19m
Deal found 25/10C$ 737
Thu 17/129:40 a.m. -
2 stops15h 56m
Wed 30/124:28 p.m. -
2 stops18h 24m
Deal found 22/10C$ 739
Thu 17/126:40 a.m. -
1 stop5h 46m
Sun 3/13:15 p.m. -
1 stop7h 17m
Deal found 22/10C$ 744
Sun 22/116:40 a.m. -
1 stop5h 46m
Sun 29/113:15 p.m. -
2 stops7h 04m
Deal found 25/10C$ 751
Sat 5/129:40 a.m. -
2 stops11h 51m
Mon 14/127:25 p.m. -
2 stops23h 30m
Deal found 21/10C$ 752

Find flight deals from Winnipeg to Portland

Round-trip from

C$ 717

One-way from

C$ 315

Popular in

December

Cheapest in

June

Average price

C$ 816
United Airlines
  • United Airlines
  • 21/1-4/2
  • 4 total stops
  • 27h 43m total
  • Winnipeg to Portland
Search Deals
6/1-31/12
  • 6/1-31/12
  • 2 total stops
  • 30h 32m total
  • Winnipeg to Portland
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 29 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 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

Wed 6/1

6:00 a.m.-4:42 p.m.

3 stops36h 42m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 375

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Thu 7/1

6:00 a.m.-5:47 p.m.

2 stops13h 47m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 378

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Sun 6/12

12:10 p.m.-5:22 p.m.

2 stops31h 12m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 388

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Fri 4/12

8:35 a.m.-10:18 a.m.

3 stops27h 43m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 394
Quickest round-trip

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Sun 6/12

6:40 a.m.-10:26 a.m.

1 stop5h 46m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 395

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Thu 7/1

9:40 a.m.-7:11 p.m.

2 stops11h 31m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 396

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Fri 22/1

7:35 p.m.-6:00 p.m.

3 stops48h 25m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 402

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Mon 21/12

12:22 p.m.-9:39 p.m.

1 stop11h 17m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 409

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Wed 6/1

9:40 a.m.-10:15 p.m.

1 stop14h 35m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 409

WinnipegPortland

YWG Winnipeg - PDX Portland

YWGPDX

Winnipeg

Tue 5/1

8:00 a.m.-7:59 p.m.

1 stop13h 59m

Portland

Wed 31/12

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

Nonstop0h 00m

C$ 409

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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$ 462). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 842). 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.

Reviews of airlines servicing Portland

Get a feel of what it's like to fly with 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.
Air Canada
7.1
Good
11,810 reviews
Check prices

Food

6.3

Crew

7.8

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had
Air Canada
7.1
Good
11,810 reviews
Air Canada
7.1
Good
11,810 reviews
Check prices

Food

6.3

Crew

7.8

Boarding

7.3

Comfort

7.1

Entertainment

6.8

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Sylvia,Aug 2026

YYZ - PHL

Our flight from Kelowna was 5 hours delayed. We missed our connection. We were able to get to a hotel by 3:00 a.m. but the breakfast cost us $40. The hotel was good. We were rescheduled for the flight the next night when it was canceled. There were no hotel vouchers available which didn't matter because there were no hotel rooms available. We decided to just drive which was not easy doing a one-way rental to the United States. Worst possible trip I've ever had

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 United Airlines or Air Canada 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 is the cheapest airline to fly from Winnipeg to Portland round-trip?

    According to our current data, Air Canada (C$ 382), offers the cheapest pricing from Winnipeg to Portland. You may be able to fly from Winnipeg to Portland for 38% less than the average price by searching for this airline.

  • 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$ 462). Flying from Winnipeg to Portland in December is currently the most expensive (average of C$ 842). 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
Gresham

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Winnipeg to Portland

Winnipeg to Medford flights

Top airline flying from Winnipeg to Portland

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 382AverageC$ 600FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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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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