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Cheap flights from Oakland, CA to Winnipeg from C$ 765

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

Cheap flight deals from Oakland to Winnipeg

Enter your travel dates to find the best prices.

Cheapest flights from Oakland to Winnipeg

Thu 12/115:55 a.m. -
2 stops8h 30m
Sat 14/1112:44 p.m. -
2 stops12h 18m
Deal found 22/10C$ 3,104
Wed 11/115:55 a.m. -
2 stops8h 30m
Sat 14/1112:44 p.m. -
2 stops12h 18m
Deal found 22/10C$ 3,225
Thu 12/115:55 a.m. -
2 stops8h 30m
Sun 15/116:35 a.m. -
2 stops12h 42m
Deal found 22/10C$ 3,645

Find flight deals from Oakland to Winnipeg

Round-trip from

C$ 765

Popular in

December

Cheapest in

January

Average price

C$ 643
15/1-18/1
  • 15/1-18/1
  • 3 total stops
  • 36h 04m total
  • Oakland to Winnipeg
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Highest demand for flights based on searches. 13% potential increase in price (C$ 153 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
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Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Oakland to Winnipeg that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Fri 15/1

10:58 p.m.-5:25 p.m.

2 stops15h 27m

Winnipeg

Mon 18/1

4:00 p.m.-9:37 a.m.

1 stop20h 37m

C$ 765
Quickest round-trip

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Wed 11/11

12:41 p.m.-12:33 a.m.

2 stops8h 52m

Winnipeg

Wed 31/12

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

Nonstop0h 00m

C$ 1,030

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Sun 17/1

5:55 a.m.-12:34 a.m.

2 stops15h 39m

Winnipeg

Wed 20/1

6:35 a.m.-11:56 p.m.

2 stops20h 21m

C$ 1,388

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Wed 13/1

5:55 a.m.-12:34 a.m.

2 stops15h 39m

Winnipeg

Sat 16/1

12:30 p.m.-11:56 p.m.

2 stops14h 26m

C$ 1,388

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Tue 12/1

5:55 a.m.-12:50 p.m.

2 stops27h 55m

Winnipeg

Thu 21/1

5:38 p.m.-11:56 p.m.

2 stops33h 18m

C$ 1,427

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Tue 12/1

5:05 p.m.-12:34 a.m.

2 stops28h 29m

Winnipeg

Sun 17/1

6:35 a.m.-12:25 p.m.

2 stops8h 50m

C$ 1,510

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Wed 11/11

5:55 a.m.-5:25 p.m.

2 stops8h 30m

Winnipeg

Sat 14/11

12:44 p.m.-10:02 p.m.

2 stops12h 18m

C$ 3,225

OaklandWinnipeg

OAK Oakland - YWG Winnipeg

OAKYWG

Oakland

Thu 12/11

5:55 a.m.-5:25 p.m.

2 stops8h 30m

Winnipeg

Sun 15/11

6:35 a.m.-4:17 p.m.

2 stops12h 42m

C$ 3,645

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/10

Sorted by cheapest first

Best time to book a flight from Oakland to Winnipeg

Have a flexible travel schedule? Discover the best time to fly to Winnipeg from Oakland with our price prediction graph.
Estimated round-trip price

Related info for your journey

  • How long is the flight from Oakland, California to Winnipeg?

    A quick flight from Oakland, California to Winnipeg can take about 15h 39m. Delta provides one of the quickest options available for as low as C$ 1,388. There are 2401 km between Oakland, California and Winnipeg.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland 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.

See more FAQs

Travelling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
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Cheapflights makes it easy to find Oakland 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 Oakland to Winnipeg?

Cheapflights simply makes it quick and affordable to book flights from Oakland to Winnipeg by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

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

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

Can Cheapflights notify me if prices for flights from Oakland to Winnipeg become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Winnipeg from Oakland today and book when prices fit your budget.

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