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Cheap flights from Oakland, CA to Winnipeg from C$ 1,274

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
27 Nov — 4 Dec1
1 adult
1 adult, Economy, 0 bags

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Cheapest flights from Oakland to Winnipeg
Explore the most affordable flight options available from Oakland to Winnipeg. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 28 October 2025.

Wed 29/1012:30 p.m.OAK - YWG
2 stops8h 57mDelta
Wed 5/115:40 p.m.YWG - OAK
2 stops8h 13mDelta
Deal found 26/10C$ 2,339

Cheap flight deals from Oakland to Winnipeg

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) 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 28 October 2025.

Round-trip from

C$ 1,274

Popular in

November

Cheapest in

September

Average price

C$ 663
Delta
  • Delta
  • 10/3-11/3
  • 4 total stops
  • 34h 01m total
  • Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland 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 629,999 searches. Data last updated 28 October 2025.
Use the filters below to find and compare flights from Oakland to Winnipeg that are best for you.

Fly from

Oakland

Fly to

Winnipeg

Route

Depart

Return

Price

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 10/3

5:55 a.m.-5:00 p.m.

2 stops9h 05m

Winnipeg

Wed 11/3

5:38 p.m.-4:34 p.m.

2 stops24h 56m

C$ 1,274

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 15/4

5:55 a.m.-4:54 p.m.

2 stops8h 59m

Winnipeg

Sun 19/4

12:40 p.m.-11:49 p.m.

2 stops13h 09m

C$ 1,311

Flights are sorted by cheapest round-trip flights first.

Deals found on 25/10

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
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 Oakland to Winnipeg

What is the cheapest month to book a flight from Oakland, California to Winnipeg?

Currently, February is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of C$ 159). Flying from Oakland, California to Winnipeg in November is currently the most expensive (average of C$ 386). 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.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Winnipeg. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    A quick flight from Oakland, California to Winnipeg can take about 9h 05m. Delta provides one of the quickest options available for as low as C$ 1,274. 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.

  • What is the cheapest month to book a flight from Oakland, California to Winnipeg?

    Currently, February is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of C$ 159). Flying from Oakland, California to Winnipeg in November is currently the most expensive (average of C$ 386). 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
Portage la Prairie

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

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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