HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Winnipeg

$255+ Cheap flights from Oakland, CA (OAK) to Winnipeg (YWG)

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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — YWG
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Winnipeg with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$651
(Delta)

One-way from

$255
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$310
Provider with most accurate pricing for Oakland-Winnipeg flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-Winnipeg flights.
Search Deals
From Oakland to Winnipeg
Search Deals
One-way flight from Oakland to Winnipeg
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Oakland to Winnipeg

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 September 25, 2025.

This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:55 amOAK - YWG
2 stops15h 41mDelta
Wed 12/36:40 amYWG - OAK
2 stops19h 28mDelta
Deal found 9/24$651
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/245:55 amOAK - YWG
2 stops15h 41mDelta
Thu 12/46:40 amYWG - OAK
2 stops19h 28mDelta
Deal found 9/24$663
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/234:57 pmOAK - YWG
2 stops29h 42mDelta
Thu 1/14:10 pmYWG - OAK
2 stops33h 48mDelta
Deal found 9/24$985
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:34 pmOAK - YWG
2 stops9h 11mDelta
Thu 1/14:10 pmYWG - OAK
2 stops33h 48mDelta
Deal found 9/24$1,086
This Delta deal was found by Cheapflights users on 9/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:53 amOAK - YWG
2 stops10h 13mDelta
Thu 1/14:10 pmYWG - OAK
2 stops33h 48mDelta
Deal found 9/24$1,099

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 2,558,603 searches. Data last updated September 25, 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 11/25

5:55 am-11:36 pm

2 stops15h 41m

Winnipeg

Wed 12/3

6:40 am-12:08 am

2 stops19h 28m

$651

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 11/24

5:55 am-11:36 pm

2 stops15h 41m

Winnipeg

Thu 12/4

6:40 am-12:08 am

2 stops19h 28m

$663

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 11/25

5:55 am-11:36 pm

2 stops15h 41m

Winnipeg

Thu 12/4

6:40 am-12:08 am

2 stops19h 28m

$663

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 3/10

5:55 am-5:00 pm

2 stops9h 05m

Winnipeg

Wed 3/11

5:38 pm-4:34 pm

2 stops24h 56m

$964

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Tue 12/23

4:57 pm-12:39 am

2 stops29h 42m

Winnipeg

Thu 1/1

4:10 pm-11:58 pm

2 stops33h 48m

$985

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 12/22

12:34 pm-11:45 pm

2 stops9h 11m

Winnipeg

Thu 1/1

4:10 pm-11:58 pm

2 stops33h 48m

$1,086

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Sun 12/21

5:53 am-6:06 pm

2 stops10h 13m

Winnipeg

Thu 1/1

4:10 pm-11:58 pm

2 stops33h 48m

$1,099

OaklandWinnipeg

OAK - YWG

OAKYWG

Oakland

Mon 10/13

10:02 am-2:13 pm

3 stops50h 11m

$255

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/25

Compare providers for flights from Oakland to Winnipeg

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Winnipeg in September.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Winnipeg flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Winnipeg flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Winnipeg flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Winnipeg flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Winnipeg flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, August is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $358). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $501). 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?

    Departing from Oakland, California to Winnipeg will take you 15h 41m. The distance from Oakland, California to Winnipeg is about 1492 mi.

  • 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, August is the cheapest month in which you can book a flight from Oakland, California to Winnipeg (average of $358). Flying from Oakland, California to Winnipeg in December is currently the most expensive (average of $501). 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

Traveling to a place near Winnipeg?

Book flights to Winnipeg if you plan to visit one of these locations
Portage la Prairie

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.