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Cheap flights from Oakland, CA to Winnipeg from C$ 256

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
24 Aug — 31 Aug1
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
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 25 July 2026.

Thu 10/910:11 a.m.
OAK
-
YWG
2 stops9h 29m
Multiple Airlines
Fri 11/92:55 p.m.
YWG
-
OAK
2 stops9h 59m
Multiple Airlines
Deal found 23/7C$ 1,474
Wed 12/86:22 a.m.
OAK
-
YWG
2 stops11h 38m
Multiple Airlines
Mon 17/87:30 a.m.
YWG
-
OAK
2 stops14h 24m
Multiple Airlines
Deal found 21/7C$ 1,916
Sun 13/96:00 a.m.
OAK
-
YWG
2 stops8h 54m
Delta
Wed 16/93:58 p.m.
YWG
-
OAK
2 stops10h 01m
Delta
Deal found 25/7C$ 2,185
Mon 27/712:30 p.m.
OAK
-
YWG
2 stops8h 59m
Delta
Sat 1/83:59 p.m.
YWG
-
OAK
2 stops7h 39m
Delta
Deal found 23/7C$ 2,263
Mon 27/76:00 a.m.
OAK
-
YWG
2 stops15h 29m
Delta
Sun 2/83:59 p.m.
YWG
-
OAK
2 stops9h 51m
Delta
Deal found 22/7C$ 2,277
Mon 27/711:15 p.m.
OAK
-
YWG
2 stops23h 40m
Multiple Airlines
Sat 1/84:15 p.m.
YWG
-
OAK
3 stops31h 29m
Multiple Airlines
Deal found 22/7C$ 2,294
Mon 27/712:30 p.m.
OAK
-
YWG
2 stops8h 59m
Delta
Fri 31/75:41 p.m.
YWG
-
OAK
2 stops8h 09m
Delta
Deal found 23/7C$ 2,457
Mon 27/711:15 p.m.
OAK
-
YWG
2 stops23h 40m
Multiple Airlines
Sun 2/86:05 p.m.
YWG
-
OAK
3 stops29h 55m
Multiple Airlines
Deal found 22/7C$ 2,463

Find 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 25 July 2026.

Round-trip from

C$ 1,449

One-way from

C$ 256

Popular in

December

Cheapest in

September

Average price

C$ 741
19/8-25/8
  • 19/8-25/8
  • 4 total stops
  • 42h 22m total
  • Oakland to Winnipeg
Search Deals
1/9
  • 1/9
  • 2 total stops
  • 25h 18m total
  • Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 130 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 58 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 25 July 2026.
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 - YWG

OAKYWG

Oakland

Wed 19/8

6:52 p.m.-11:40 p.m.

2 stops26h 48m

Winnipeg

Tue 25/8

9:20 a.m.-10:54 p.m.

2 stops15h 34m

C$ 1,449

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Thu 10/9

10:11 a.m.-9:40 p.m.

2 stops9h 29m

Winnipeg

Fri 11/9

2:55 p.m.-10:54 p.m.

2 stops9h 59m

C$ 1,474

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 12/8

6:22 a.m.-8:00 p.m.

2 stops11h 38m

Winnipeg

Mon 17/8

7:30 a.m.-7:54 p.m.

2 stops14h 24m

C$ 1,916
Quickest round-trip

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 21/8

6:00 a.m.-4:52 p.m.

2 stops8h 52m

Winnipeg

Fri 28/8

3:58 p.m.-11:56 p.m.

2 stops9h 58m

C$ 2,844
Cheapest one-way

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 1/9

6:52 p.m.-10:10 p.m.

2 stops25h 18m

C$ 256
Quickest one-way

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sat 29/8

6:00 a.m.-11:30 p.m.

2 stops15h 30m

C$ 669

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 2/9

5:00 p.m.-11:54 a.m.

2 stops16h 54m

C$ 683

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 31/8

6:00 a.m.-11:30 p.m.

2 stops15h 30m

C$ 690

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Thu 3/9

5:00 p.m.-11:54 a.m.

2 stops16h 54m

C$ 834

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 6/9

5:00 p.m.-8:00 p.m.

2 stops25h 00m

C$ 852

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/7

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
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.

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 8h 52m. Delta provides one of the quickest options available for as low as C$ 2,844. 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
Selkirk

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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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