HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Oakland

$593+ Cheap flights from Winnipeg (YWG) to Oakland, CA (OAK)

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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
YWG — OAK
Mar 1 — Mar 81
Sun 3/1
Sun 3/8
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Winnipeg to Oakland 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 Winnipeg to Oakland

Cheapest flights from Winnipeg to Oakland
Explore the most affordable flight options available from Winnipeg to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.

This Delta deal was found by Cheapflights users on 1/29. 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 4/65:20 pm
YWG
-
OAK
2 stops20h 31m
Delta
Fri 4/175:04 pm
OAK
-
YWG
2 stops28h 26m
Delta
Deal found 1/29$593
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/64:10 pm
YWG
-
OAK
3 stops31h 01m
Multiple Airlines
Fri 4/1711:16 pm
OAK
-
YWG
2 stops23h 23m
Multiple Airlines
Deal found 1/29$879

Find flight deals from Winnipeg to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Winnipeg (YWG) to Oakland (OAK). 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 January 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$593
(Delta)

Popular in

December

Cheapest in

September

Average price

$266
Provider with most accurate pricing for Winnipeg-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Winnipeg-Oakland flights.
Search Deals
From Winnipeg to Oakland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($51 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Winnipeg to Oakland 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 January 30, 2026.
Use the filters below to find and compare flights from Winnipeg to Oakland that are best for you.

Fly from

Winnipeg

Fly to

Oakland

Route

Depart

Return

Price

WinnipegOakland

YWG - OAK

YWGOAK

Winnipeg

Mon 4/6

5:20 pm-11:51 am

2 stops20h 31m

Oakland

Fri 4/17

5:04 pm-11:30 pm

2 stops28h 26m

$593

WinnipegOakland

YWG - OAK

YWGOAK

Winnipeg

Mon 4/6

4:10 pm-9:11 pm

3 stops31h 01m

Oakland

Fri 4/17

11:16 pm-12:39 am

2 stops23h 23m

$879

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

  • Most accurate provider: When it comes to deals on Winnipeg-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Winnipeg-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Winnipeg-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Winnipeg-Oakland, California 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 Winnipeg-Oakland, California 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 Winnipeg to Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland from Winnipeg 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 Winnipeg to Oakland

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

Currently, October is the cheapest month in which you can book a flight from Winnipeg to Oakland, California (average of $139). Flying from Winnipeg to Oakland, California in December is currently the most expensive (average of $217). 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 Winnipeg to Oakland. 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 Winnipeg to Oakland, California?

    Delta can get you from Winnipeg to Oakland, California in just under 20h 31m. Your travel time can differ by up to . Airlines will cover a distance of 1492 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Winnipeg to Oakland 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 Winnipeg to Oakland, California?

    Currently, October is the cheapest month in which you can book a flight from Winnipeg to Oakland, California (average of $139). Flying from Winnipeg to Oakland, California in December is currently the most expensive (average of $217). 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

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.
Site
Cookie settings©2026 Cheapflights