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Cheap flights from Oakland, CA to Winnipeg from C$ 452

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 28/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
9 Apr — 16 Apr1
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 10 March 2026.

Wed 29/710:20 a.m.
OAK
-
YWG
2 stops9h 20m
Multiple Airlines
Thu 6/812:50 p.m.
YWG
-
OAK
2 stops12h 09m
Multiple Airlines
Deal found 7/3C$ 974
Thu 13/85:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Tue 25/88:50 a.m.
YWG
-
OAK
2 stops33h 41m
Delta
Deal found 6/3C$ 1,015
Sun 16/85:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Sat 22/86:40 a.m.
YWG
-
OAK
2 stops19h 09m
Delta
Deal found 6/3C$ 1,023
Mon 3/85:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Sat 8/86:40 a.m.
YWG
-
OAK
2 stops16h 54m
Delta
Deal found 6/3C$ 1,034
Wed 15/47:00 a.m.
OAK
-
YWG
2 stops15h 41m
Multiple Airlines
Sat 18/45:55 a.m.
YWG
-
OAK
2 stops13h 51m
Multiple Airlines
Deal found 5/3C$ 1,037
Tue 28/710:20 a.m.
OAK
-
YWG
2 stops9h 20m
Multiple Airlines
Wed 5/812:50 p.m.
YWG
-
OAK
2 stops12h 09m
Multiple Airlines
Deal found 8/3C$ 1,039
Sun 2/85:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Mon 10/88:50 a.m.
YWG
-
OAK
2 stops16h 59m
Delta
Deal found 6/3C$ 1,042
Mon 3/85:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Mon 10/86:40 a.m.
YWG
-
OAK
2 stops19h 09m
Delta
Deal found 6/3C$ 1,053
Tue 28/75:55 a.m.
OAK
-
YWG
2 stops15h 32m
Delta
Tue 4/84:09 p.m.
YWG
-
OAK
2 stops9h 40m
Delta
Deal found 9/3C$ 1,109
Mon 27/710:20 a.m.
OAK
-
YWG
2 stops9h 20m
Multiple Airlines
Wed 5/812:50 p.m.
YWG
-
OAK
2 stops12h 09m
Multiple Airlines
Deal found 7/3C$ 1,129
Mon 5/108:00 a.m.
OAK
-
YWG
2 stops10h 00m
Multiple Airlines
Tue 13/106:00 a.m.
YWG
-
OAK
2 stops15h 19m
Multiple Airlines
Deal found 6/3C$ 1,261

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 10 March 2026.

Round-trip from

C$ 974

One-way from

C$ 452

Popular in

December

Cheapest in

September

Average price

C$ 645
29/7-6/8
  • 29/7-6/8
  • 4 total stops
  • 21h 29m total
  • Oakland to Winnipeg
Search Deals
28/7
  • 28/7
  • 3 total stops
  • 21h 00m total
  • Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 183 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 62 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 10 March 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
Quickest round-trip

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 29/7

10:20 a.m.-9:40 p.m.

2 stops9h 20m

Winnipeg

Wed 5/8

12:50 p.m.-10:59 p.m.

2 stops12h 09m

C$ 974

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Thu 30/7

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Tue 11/8

8:50 a.m.-11:49 p.m.

2 stops16h 59m

C$ 1,015

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 31/7

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Wed 12/8

8:50 a.m.-11:49 p.m.

2 stops16h 59m

C$ 1,015

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 2/8

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Tue 11/8

8:50 a.m.-11:49 p.m.

2 stops16h 59m

C$ 1,023

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 14/8

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Sun 23/8

8:50 a.m.-11:49 p.m.

2 stops16h 59m

C$ 1,034

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 3/8

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Tue 11/8

6:40 a.m.-11:49 p.m.

2 stops19h 09m

C$ 1,034

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Fri 31/7

5:05 p.m.-11:27 p.m.

2 stops28h 22m

Winnipeg

Mon 10/8

6:40 a.m.-11:49 p.m.

2 stops19h 09m

C$ 1,034

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Wed 15/4

7:00 a.m.-12:41 a.m.

2 stops15h 41m

Winnipeg

Sat 18/4

5:55 a.m.-5:46 p.m.

2 stops13h 51m

C$ 1,037

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 28/7

10:20 a.m.-9:40 p.m.

2 stops9h 20m

Winnipeg

Wed 5/8

12:50 p.m.-10:59 p.m.

2 stops12h 09m

C$ 1,039

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 28/7

5:55 a.m.-11:27 p.m.

2 stops15h 32m

Winnipeg

Tue 4/8

4:09 p.m.-11:49 p.m.

2 stops9h 40m

C$ 1,109

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 11 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of C$ 155). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of C$ 524). 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 15h 32m. Delta provides one of the quickest options available for as low as C$ 1,015. 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, June is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of C$ 155). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of C$ 524). 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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